Italicized configurational prefixes (as glycero-) are used as main entries, whereas other italicized prefixes (as scyllo-) are listed under the stem name.
A Absolute configuration, 15 Acacia species, 685, 510
gum arabic, 685
Acetaldehyde, see also Ethylidene de- rivatives, 235
Acetals, see also Alkylidene derivatives, individual aldehydes and ke- tones, individual sugars, and Anhydro sugars,
acetal type, 227 alkali labile, 390 definition, 188 preparation, 157, 288 Acetamide derivatives, 408
Acetates, see also Acetylation, Es- ters, Esterification, Orthoace- tates and individual compounds, 139
ΑΓ-acetyl groups hydrolysis, 650
resistance to alkali, 463 acetyl migration, 147, 408 acyclic, 139, 142, 144 aldehydo, 139, 142
anomerization, 141, 483, 495
distinction between N- and O-acetyl groups, 410
enhancement of rotation (alditols), 260 furanose, 141
keto, 139, 144 polysaccharides, 692
estimation of hydroxyl groups, 648 preparation of aryl glycosides, 198 pyranose, 139
replacement of anomeric acetate byhalide, see O-Acylglycosyl halides by nitrate, 169
septanose, 146
Acetic acid, labeled, degradation, 624
* Subject Index compiled by James W. Pratt.
Acetoacetic ester, 240
synthesis of DL-mannitol, 250 reactions with sugars, 240 Acetobacter species,
A. acetigenum, 708 cellulose synthesis, 708 A. suboxydans, 98, 133, 365
action on inositols, 282 preparation of
1,6-labeled ketoses, 136 planteobiose, 501 A. xylinum, 98, 102, 132, 365
cellulose synthesis, 707
Acetohalogeno sugars, see O-Acetylgly- cosyl halides; also Acetates and individual sugars
Acetolysis,
anhydro compounds, 394 anhydro sugars, acetal type, 223 méthylène groups, 232
polysaccharides, 702
Acetone derivatives, see Isopropylidene Acetylation, see also Acetates, Ortho-
acetates, and individual com- pounds, 139
aminodeoxy sugars, 471
anomeric ratio, conditions affecting, 140 as analytical procedure, 140
catalysts, 139, 140, 692 effect of pH on rate, 140 glycosylamines, 408 tautomers, 140 Acetylene,
synthesis of alditols, 242, 244 ethylidene compounds, 235 β-N- Acetylglucosaminidase,
alfalfa emulsin, 590 almond emulsin, 577 O-Acetylglycosyl halides, 150
formation of anhydro sugars, acetal type, 222
Achromycin, 465 Achroic point, 681 851
Achroic R-value, 681
Acids (mineral), see also 2-Furaldehyde, Levulinic acid, Anhydro sugars, acetal type, and individual sugars
condensation (polymerization) reac- tions, 59
dehydration reactions, 57 glycoside formation, 59
"reversion", 60
Acids, Organic, see also Aldonic, Aldaric, Uronic and individual acids peroxy acids, 360
oxidation of glycals, 400 thioacetals, 360 Acofriose, 553 Acorn, 274 Acovenose, 553
a-Acritol (see DL-Mannitol), 250 Acrolein dibromide, 103 a-Acrose, 104
phenylosazone, 103 reduction, 250 Acrylonitrile,
cyanoethylcellulose, 695
*'Active glycolaldehyde,,, 770 acceptors, 771
donors, 770
Acyclic sugars, see also aldehydo and keto sugars, 226
O-Acylhalogeno sugars, see O-Acylgly- cosyl halides
Acyl migration, 175, 408 O-Acylglycosyl fluorides,
epimerization, 482
O-Acylglycosyl halides, see also Ace- tates, Benzoates and individual sugars, 150, 153
acyclic, 157
addition to anhydro sugars, 485 2-deoxy, 401
furanose, 156 hydrolysis, 152
''neighboring group" effect, 153, 157 reactions with,
amino acids, 447 nitrogenous bases, 417 reduction, 383
relative stabilities, 151
substitution reactions, mechanism, 153
synthesis, 151 synthesis of,
1,2-glycoseens, 402 glycosides, 197, 552
aryl, 190 aryl, thio-, 555 glycosylamines, 416 nucleosides, 429 oligosaccharides, 483 thiocyanates, 416
O-Acylglycosyl phosphates, 174
Acyl halides (Aldonyl halides), 144, 309 reduction to aldehydo sugars, 144 Adenine, 425
nucleosides, 424
Adenosine (D-Ribosyl-N-adenine), 84, 425 diphosphoric acid (ADP), 435
synthesis, 436
triphosphoric acid (ATP), 435 high energy phosphate bonds, 749 mixed anhydride formation, 436 sucrose synthesis (enzymic), 521 synthesis, 436
Adenylic acid, 431 Adhesives, 678 Adonis vernalis, 246 Adonitol, see Ribitol Aerobacillus macerans, 681
cyclic dextrine, 681 Aerobacter species,
A. aerogenes, 620 A. levanicum, 530 levan-sucrase, 706 Agar, 88, 90, 685
structure, 685 use, 686 Agarobiose, 511
Aglycon; aglycon group, 190 Alanine, N-D-glucosyl-, 447
Alcian Blue 8GS, histochemical use, 634 Aldaric acids, see also Tetraric, Pentaric, etc., and individual acids, 3, 310-14
as intermediates, 314 preparation of dialdoses, 335 Aldazimes, 462
Aldehyde-ammonia structure (glycosyl- amines), 411
aldehydo Sugars,
O-acetyl, mutarotation, 145 preparation, 144
proof of structure, 54
reaction with acyl halides, 157 Schiff reaction, 144
Aldehydrols, O-acetyl, 703 Alditoleens, 405
Alditols, see also individual compounds, 3, 241-267
O-alkylation, 265 aminodeoxy, 261, 409
formation of anhydro derivatives, 378
preparation, 475-6 biochemistry, 266 biosynthesis, 763 chromatography, 265
"complexes", 262 configuration, 258, 262 1-deoxy-l-nitro, 476 esterification, 261 etherification, 265 nitrates, 261
nutritional aspects, 796 occurrence, 241 optical activity, 258
in aqueous borax, 171
in molybdate, molybdic acid, 259 oxidation, 264
qualitative determination, 265 quantitative determination, 265 reactions, 261-4
reduction, 265 synthesis, 241, 260 structure, 258
use in structural determinations, 258 Aldobioronic acids, 318
hydrolysis, 319 isolation, 319, 669 occurrence, 320 pseudo, 319 Aldolase, 183
configurations of condensation prod- ucts, 759
general reaction, 758 steric control, 114 Aldol condensation, 105, 759
aldolase catalysis, 758 asymmetric catalysts, 114
D-glycerose with dihydroxy acetone, 113
steric factors, 114
Aldonate esters, 162 Aldonic acids, 3, 301-310
acyl chlorides, 309 reduction, 144 amides, 308 2-amino-2-deoxy,
epimerization, 472 preparation, 472 as intermediates, 301 benzimidazole formation, 414 biosynthesis, 763
characterization of sugars, 301 2-deoxy, 401
epimerization, 302, 305 esterification, 308 hydrazides, 309
hydrolysis, 309 2-keto, 325
acid decomposition, 327 enolization, 326 Ruff degradation, 327 synthesis, 326 5-keto, 325
acid decomposition, 327 behavior toward oxidants, 326 synthesis, 326
quantitative estimation, 327
optical rotatory relationships and
"rules", 306 pharmaceutical use, 301 phenylhydrazide formation, 415 polymerization, 305
preparation, 302
reactivity, influence of cations, 308 reduction, 310
salts, 308 solubilities, 308 synthesis, total, 303 thiol esters, reduction, 261 Aldonic lactones, 304
epimerization, 305
equilibrium with corresponding acid, 304
hydrazides, 462 mutarotation, 303, 304 reactions with alkalies, 308 reducing action, 313 test for, 308 Aldononitriles, 464
Aldoses, see also Monosaccharides, Su- gars and individual compounds, 24
conversion to ketoses, see also Lobry de Bruyn-Alberda van Eken- stein, Glycals, Osones, 134 2-deoxy, preparation, 400
6-deoxy, in cardiac glycosides, 553 2-deoxy-2-halogeno, osazone forma-
tion, 401 labeled (Cl), 135 quantitative estimation,
chloride method, 346 hypoiodite method, 343, 617 Kiliani reaction, 618
Alduronic acids, see Uronic acids Alfalfa emulsin, glycosidase system, 590 Algae, 99
glycerol D-galactoside, 88 polysaccharides, 686 Porphyr a umbilicalis, 94 Algin, industrial use, 687 Alginic acid, 687
nutritional aspects, 799 structure, 687
Alizarin, 551 Alkali, action on,
aryl glycosides, 221 polysaccharides, 653
nature of glycosidic linkages, determination, 653
sugars, 60-69
deep-seated rearrangements, 63 dependence on cations, 65
fragmentation and condensation, 65 internal oxidation-reduction, 65 lactic acid production, 66 mutarotation, 55
saccharinic acids, 66
effect of alkali concentration, 68 Alkali number (starch), 649
O-Alkylation, see also Methylation, and Triphenylmethylation, 369 alkyl iodide-alkoxide method,
sodium, 370 silver, 370 thallium, 371
alkyl sulfate-alkali method, 369 formation of glycosides, 202
order of reactivity of hydroxyl groups, 372
selective, 371
C-Alkyl compounds, preparation, 117 O-Alkyl derivatives, see Ethers Alkylidene derivatives, see also Ben-
zylidene, Ethylidene, Isopropyl- idene, Méthylène and individual compounds, 229-240
formation, 229 in synthesis, 232 ring shifts, 230 ring size, 230 Alligator pear, 101
Allihn method (reducing sugars), 614 Allitol, 252
from D-glueose, 63 total synthesis, 106 Allium species, 520 Allodulcitol, see Allitol D-Allose, 24
D-Allopyranoside, methyl, 2,3-anhydro, 168 3,4-anhydro, 168 Allyl alcohol, 105
Allyl ethers, polymerization, 369 Allyl isothiocyanate, from sinigrin, 554 Almond emulsin, 563, 575
effect of pH on activity, 576 effect on pentosides, 577 enzymes present, 577 ß-glucosaminidase, 473 /3-glucuronidase, 596
hydrolysis of nucleic acids, 426 preparation and purification, 575 Aloe barbadensis, 83
Aloins (cathartic-acting glycosides), 83 D-Altritol, see D-Talitol
D-aZiro-Heptulose (Sedoheptulose), 101, 259
action of acid, 102 2,7-anhydro, 102,81
tetra-O-benzoyl, 81 enzymic synthesis, 759
in carbohydrate metabolism, 102 in "pentose pathway", 183 in photosynthesis, 102 labeled, degradation, 624 occurrence, 102
7-phosphate, 183
hexose monophosphate shunt, 770 metabolism, 771
photochemical production, 753 1,7-diphosphate, 183, 772 preparation, 102 D-Altrose, 24
2-amino-2-deoxy, from D-glucal, 470 4-0-0-D-galactosyl, 482
4-0-0-D-glucosyl, 482
methyl 2,6-anhydro-a-D-altroside, 375 phenylosazone, 3,6-anhydro, 387 synthesis, 168, 482
Aluminum chloride on acetylated sugars, formation of O-acylglycosyl halides,
151 inversions, 482
Amadori rearrangement, see also Ami- nodeoxy sugars and individual sugars 135, 422
in phenylosazone formation, 456 ketosylamines to aldoses, 423 mechanism, 423
"reverse", 423 Amice tin, 425
û>-(p-Aminoacetophenone) ethers of cel- lulose, 369
Amino acids,
acylation of aminodeoxy sugars, 448 iV-aldonyl derivatives, 450
combinations with carbohydrates, 446- 450
configuration, correlations with L-glyc- erose, 28
nomenclature, 28
Aminodeoxyalditols, see Alditols Aminodeoxyhexoses, see also Amino-
deoxy sugars and individual compounds,
quantitative and qualitative test, 650 Aminodeoxy sugars, see also Glycosyl-
amines and individual sugars 3, 407, 465
2-amino-2-deoxy, 465 3-amino-3-deoxy, 465 o-amino-co-deoxy, 470 iV-acetylation, 471
oxazoline formation, 474 analysis, 474
anhydro derivatives, 378 biosynthesis, 471
configuration, 449
Elson and Morgan procedure, 650 glycosides, 472
hydrolysis, 472 isolation, 469
nutritional aspects, 797 occurrence, 465 preparation, 391, 468 reactions, 471
with amino acids, 448 Schiff bases, 471
selective deacetylation, 471 structure, 466
synthesis, 469
Aminopyrimidines, condensation with sugars, 415
Amino sugars, see Aminodeoxy sugars Ammonia,
action on aldehy do-glucose pentaace- tate, 408
ammonolysis, 391, 467 as solvent, 370
glycosylamine formation, 407 hexosamine formation, 469-471 hydrolysis of nucleic acids, 425 Ammonium,
chloride, catalytic action, 408, 412 hydrogen sulfide, reductive denitra-
tion, 170
molybdate, effect on rotations, 259 amphi compounds, Rosanoff definition,
26
Amygdalin, 492, 550 sugar moiety, 492 synthesis, 550
Amygdalose, see Gentiobiose
Amygdalus communis (/3-glucosidase), 588
Amylases, 678 a-amylases, 678 ß-amylases, 678 action on glycogen, 715 crystalline, 679 liquefying, 678 saccharogenic, 678 selective inactivation, 679 Amylo-(l —* 6)-glucosidase, 683
"Amyloid", 637
Amylomaltase, polysaccharide synthesis, 704
Amylopectin, 94, 675 isolation, 675
nutritional aspects, 805 parenteral feeding, 805 structure, 675
synthesis of amylopectin-type poly- saccharide, 705
Amylopsin, 678 Amylose, 675
acetate, 678
film-forming properties, 678 action of phosphorylase, 682
behavior in cuprammonium solution, 676
conformation of D-glucose units, 676 cyclohexaamylose, 682
iodine reaction, 676 isolation, 675 structure, 675
synthesis of amylose-type polys ac- charides, 704
Amylosucrase, polysaccharide synthesis, 705
1-Amyl-l-phenylhydrazine, 90 Angelica lactones, 58
Anhydroalditols, see also Anhydro de- rivatives (general),
esters, partial, 397
industrial applications, 397 glycol cleavage, 396
inversions during formation, 386 oxidation, 395
nitrates, 397
substitution products, 396 synthesis, 382, 384
Anhydro compounds (general), benzimidazoles, 387, 414 formation,
mechanism, 376 steric requirements, 376
intramolecular rearrangements, 378 phenylosazones, 387, 461
preparation, 376 ring size, 375 ring scission, 390
acetolysis, 394 ammonolysis, 391, 467 direction of opening, 393-4 hydrolysis, 390
inversions, 390 methoxide ion, 390
reductive, 393
solvolysis, general, 391 stability, 378
Anhydro sugars, acetal type (glycosans), see also Anhydro sugars, ether type, 188, 220-225
acetolysis, 223
1,6-anhydrohexof uranoses,
resistance to periodate oxidation, 217 diketose dianhydrides, 224
preparation, 221
alkali on aryl glycosides, 221 mineral acid on sugars, 222 reactions, 223
structure determination, 222 synthesis of oligosaccharides, 484
sucrose, 485
Anhydro sugars, ether type, 188, 375-399
"Non-reducing" anhydro sugars (gly- cosans) are listed as Anhydro sugars, acetal type
aminodeoxy sugars, 468, 470 5,6-anhy drohexoses,
reactions with amino acids, 448 2,5-anhydro sugars, osazone forma-
tion, 395
methyl 3,6-anhydroaldohexopyrano- sides, 389
py ranose-f uranose transformations, 388
reactivity, effect of anhydro ring, 388 synthesis of oligosaccharides, 483, 485 Anilides, see also iV-phenylglycosyl-
amines, 415 Aniline, reactions with
acids, lactones, salts, 415 sugars, 412
Anomeric substitution, see also Koenigs - Knorr reaction, 194
Anomers, 31 anomerization,
acetates, 151
factors controlling, 156
configuration, by infrared spectra, 41 nomenclature, 42
structural significance, 42 of acyclic derivatives, 43 Anthocyanidin glycosides, 538 Anthocyanins, 538
leucoanthocyanins, 539 Anthoxanthins, 538
Anthrone, 617 Antigens,
blood group, 721 Forssman, 729 synthetic, 450
specificity related to carbohydrate, 451
Wasserman, 729 Antioxidants, 163 Aorta polysaccharide, 712 Aphid, 532
Aphio spiralcola, 532 Apiin, 553
Apiose, 78, 553 structure, 79 Apples, 95
Apricot (0-glucosidase), 588 Apurinic acid, 444
Arabans, in pectic substances, 671 Arabic acid, 685
D-Arabinitol, 243 umbilicin, 243 DL-Arabinitol, 244 L-Arabinitol, 244
D-ara&ino-Hexosone (D-glucosone), 395 2,3,4,6-tetra-O-acetyl, 334
behavior toward glycol cleaving agents, 334
1,2:2, 3:5,6-tri-0-isopropylidene, 334 5,6-di-O-methyl, 334
1-phenyl, 335 D-Arabinonic acid,
3-(j8-D-galactopyranosyl), 356 3-(0-D-glucopyranosyl), 356 1,4-lactone,
2,3,5-tri-O-methyl, 505 D-Arabinose, 19, 83
4-O-formyl-2-O-methansulfonyl, 351 dimethyl acetal, 227
methyl tri - 0 - acetyl - ß - D -arabinopy- ranoside, 157
nutritional aspects, 795 occurrence, 83
preparation, 83 synthesis, 118 L-Arabinose, 79
2,5-anhydro, 395 osazone formation, 395 3-O-jS-L-arabinopyranosyl, 510 l,2:3,4-dicarbonate, 159 3-O-a-D-galactopyranosyl, 510
3-O-a-D-glucopyranosyl, 526 synthesis (enzymic) 526 hydrazones, 80
methyl 2,5-anhydro-L-arabinofurano- side, 389
hydrolysis, 389 occurrence, 79 preparation, 83
5 (or 4)-0-j8-D-xylopyranosyl, 512 O-arabino-3,4,5,6-Tetraacet oxy-1,1 -bis-
(ethanesulfonyl) -1 -hexene, 361 Arabitol, see Arabinitol
Arabonic acid, see Arabinonic acid Arbutin, 547
methyl, 547
Aretostaphylos uva-ursi, 547 Argentic ion, 347
Arlitan, see D-Glucitol, 1,4-anhydro Arsenate, effect on enzymic transglu-
cosidation, 530, 682
C-Aryl compounds, preparation, 117 Ascophyllum nodosum, 99
L-Ascorbic acid (Vitamin C), 331 biosynthesis, 763
precursors, 764
equilibrium with dehydro-ascorbic acid, 332
histochemical detection, 637 methylation, 332
occurrence, 331 mono-O-palmitate, 163 stability, 332
synthesis, 333
D-Ascorbic acid, synthesis, 115 Ascorbic acids, (general), 328-31
acidity, 331 nomenclature, 329 preparation, 330 reducing action, 331 structure, 329 Ash, 500
manna, 515, 519 Asparogosan, 683 Aspergillus species, 250
A. foetidus, enzyme system, 667 A. nicert 365
"NRRL 337", 533
crude enzymes, action on cellulose, 664
ß-glucosidase, 588 inulases, 683
mycodextran, 706 polysaccharides, 688 A. oryzae,
ß-glucosidase, 588 transfructosidase, 707 inulobiose, 534 Asphodelan, 683
Astragalus family, gum tragacanth, 685 Avocado, 253
Azaquinine, enzymic synthesis, 426 Azotobacter vinelandii, 445
B
Bacillus species, levan-sucrase, 706 B. macerans, 705
cyclic dextrine, 705 B. megatherium, 620-1 B. mesentericus, 681 B. friedländeri, 620-1 Bagasse, 502
Barbaloin, 83
Barfoed method (reducing sugars), 616 Barium hydroxide, isolation of sucrose,
504
"Barium saccharate,,, 504 Barry reaction, 701 Basophilia, 629
extinction point, 630 Bassorin, 686
Bearberry leaves, 547 Beef lung, 88
galactan, 716 Beet pulp, 83 Behenic acid, 560
"Bemberg", 663
Benedict method (reducing sugars), 614 Benzaldehyde, see also Benzylidene and
individual compounds, 233 Benzenediazonium chloride,
formazans, 455, 460 Benzidine, Tauber's test, 607 Benzilic acid rearrangements, 68 Benzimidazole,
l-D-ribofuranosyl-5,6-dimethyl, 425 2-styryl, 624
Benzimidazole rule, 307 Benzimidazoles, 609
anhydro derivatives, 387, 414 from acids (aldonic, aldaric, sac-
charinic, etc.), 414 from sugars, 413
isolation as copper salts, 610 labeled, degradation, 624 virus inhibition, 414
Benzoates, see also individual sugars, 148
acyl migration, 149 partially esterified, 149
borates as intermediates, 149, 171 selective esterification, 149
Benzohalogeno sugars, see O-Benzoyl- glycosyl halides; also Benzoates and individual sugars
Benzoin condensation, 115 O-Benzoylglycosyl halides, 150 Benzyl ethers, hydrogenolysis, 368 Benzylidene derivatives, 233
alkali labile, 390 formation, rules, 231 hydrogenolysis, 234
Dibenzyl phosphorodichloridate, syn- thesis of phosphates, 174, 436 Bertrand method (reducing sugars), 615 Bertrand Rule, 133
Best's carmine stain, glycogen, histo- chemical, 638
Beta vulgaris, 274
manufacture of sucrose, 504 Betitol, 276
Bioinosose, see mi/o-Inosose-2
Birefrigence, streaming, polysaccha- rides, 643
Black mustard, 554 Blackstrap, 503
Blocking groups, see also Benzyl, Benzylidene, Borates, Tri- chloroacetyl, Ethylidene, Iso- propylidene, Méthylène, Tri- phenylmethyl, and individual compounds, 158
Blood-group polysaccharides, 721 from salivas, 728
occurrence, 721 structure, 721
Blood sugar, see D-Glucose Blueberries, 138, 149
Borate complexes, see Borates Borates, 171, 262
as blocking groups, 149, 171 electrophoresis, 604
ion-exchange chromâtography, 171, 603
ionization, 171 ionophoresis, 604
of alditols, effect on rotation, 171 Borax, effect on rotation, 259 Boric acid, see also Borates, 262
aminodeoxysugars, separation, 475 titration in presence of mannitol, 263 Bornesitol, 274
Bostrychia scorpoides, 248 Brachiose, see Isomaltose Brain sugar, see D-Galactose Branched chain sugars, 78
Branching enzyme, polysaccharide syn- thesis, 705
Brassica nigra Koch, 554
BrigPs anhydride (1,2-Anhydro-tri-O- acetyl-a-D-glucopyranose), see D-Glucose derivatives
British gums, 677 Bromine,
action on starch, 699 oxidation,
"electrolytic" method, 339 ketoses, 291, 339
polyols, 339 rates, 341-2
•y-Bromocrotonaldehyde, 105
iV-Bromosuccinimide, hydroxylation of double bond, 245
Browning reaction, see Melanoidin re- action
Brown rots, 665
Bupleurum jalactum, 246 Burdock, 96
Butadiene, 164 C Calcium,
hydroxide, isolation of sucrose, 504 saccharate, tri, 504
utilization, effect of lactose, 794 Calf liver, /3-glucuronidase, 596 Calf spleen, /3-glucuronidase, 596 Caffeic acid, 278
Cane sugar, see Sucrose
Cannizzaro reaction, 2-amino-2-deoxy- D-glucose, 476
Canna species, synthesis of sucrose, 524 Carageenan, 685
separation of polysaccharides, 687
structure, 687 use, 686
Carbamates, polysaccharides, 695 Carbanilates, 160
polysaccharides, estimation of second- ary hydroxyl groups, 648 Carbazole, estimation of
sugars, 617
uronicacids in polysaccharides, 648 Carbodiimide reagent, 176
Carbohydrases, 562 commercial value, 562 effect of pH, 570 history, 562 Carbohydrates, 2
biochemistry, 766-779 biosynthesis, 757-766 color reactions, 607-8 dental aspects, 807-14
"Artificial Mouth" studies, 811 decay,
incidence, 809 types of attack, 812
experimental animal studies, 810 oral clearance factor, 812 oral microflora, 814
post-eruptive effects, 808-11 pre-eruptive effects, 808 saliva, 814
histochemistry, 624-40 isotope procedures, 622-4 metabolism,
glycolysis, 766-75
interconversion of sugars, 775-7 pathways, 766
•pyruvic acid oxidation, 777 nutritional aspects, 779-814
absorption, 781 appetite, 800
blood glucose and the urge to eat, 801
caloric value, 780
candy and "soft drinks", 803 digestion, 781
parenteral feeding, 805 protein-sparing action, 803 sources, 779
utilizability, estimation, 795 weight control, 801-804 oxidation products, 299 oxidizable groups, 299
photosynthesis, 733-57 qualitative analysis, 602-10 quantitative estimation, 610-22 synthesis, cell-free system, 755 Carbomycin, 466
Carbonates, 158
furanoside formation, 203 hydrolysis, 159
Carbon chain lengthening, see also Cyanohydrin, Diazomethane, Friedel-Crafts, Grignard, Nitro- me thane, 106
glycosylamines, 469
Carbon chain shortening, see also Löwen- feld, MacDonald-Fischer, Ruff, Weerman, Weygand, Wohl deg- radations, Glycals, Hydrogen peroxide, Lead tetraacetate, Oxygen, Periodate, and indi- vidual sugars, 118
Carbon dioxide fixation, see also Photo- synthesis, 733
appearance of carbohydrates, 750 chemosynthetic (chemautotrophic),
743
Carbon disulfide, 159
xanthates, polysaccharides, 694 Carbonyl chloride, 159
1-Carboxy-D-arabinose, see D-Gluconic acid, 2-keto
Carboxy dismutase, 755 2-Carboxypyrrole, 731 Cardiac glycosides, 543 Carob bean, 250
galactomannans, 684 Carotene, 740
occurrence, 741 Cartilage, 469
chondromucoid, 723 Cataracts, 792 Cataractogenesis,
D-galactose, 89, 792 D-xylose, 85, 796
Cathartic-acting glycosides, 83 Cellobiose, 490
homologs, 491 metabolism, 491 nutritional aspects, 795 octaacetate, 490
preparation from cellulose,
acetolysis, 490 enzymic, 490 structure, 491, 500
Cellotriose, -tetraose, -pentaose, etc., Celluloid, 692 491
Cellulose, 662-5
acetate, commercial preparation, 692 azo dyes, 369
biological utilization, 663
cuprammonium rayon (Bemberg), 663 degree of polymerization, 662
effect of acids, enzymes, 664 esterification, 692
ethers, 695
co-(p-aminoacetophenone), 369 carboxymethyl, 695
cyanoethyl, 695 ethyl, 695 hydroxyethyl, 696 methyl, 695
solubility, 369 mercerization, 663 nitrate, 168
nutritional aspects, 797 dietary fiber, 798 in ruminants, 798
saccharification of wood, 799 oxidation,
analysis of groups formed, 697 periodate-oxidized, structure, 701
"tendering", 697
physical characteristics, 662 soda cellulose, 694
swelling, 663
synthesis, enzymic, 707
Celtrobiose, see D-Altrose, 4-0-/3-D- glucosyl
Cephalin, 272 Cerebrosides, 88, 560
fatty acid components, 560 structure, 560
Cerebrose, see D -Galactose Ceric sulfate, 361-2 Chaemerops humilis, 275 Chaetonium globosum, 664 Chei-Hou, 246
Chicory, 96
Chinese rhubarb, 161 Chinovin, 100
Chinoyose, see D-Glucose, 6-deoxy Chitaric acid, see D-Glucaric acid, 2,5-
anhydro Chitin, 465, 715
occurrence, 715 isolation, 715 structure, 715
Chitobiose octaacetate, 715
Chitonic acid, see D-Mannonic acid, 2,5-anhydro
Chitosamine, see D-Glucose, 2-amino-2- deoxy
Chitosaminic acid, see D-Gluconic acid, 2-amino-2-deoxy
Chitose, see D-Mannose, 2,5-anhydro Chalamydomonas eugametos, 541 Chloric acid, preparation of 2-keto-
aldonic acids, 345 Chlorine,
as oxidant, 342
oxidation of glycoseens, 335
Chloroacetic acid, preparation of car- boxymethylcellulose, 695 Chlorogenic acid, 278
Chlorous acid, 345
polysaccharides, aldehyde and ketone groups, 649
Chloroplasts, 735 composition, 736 structure, 735 Chlorophyll, 741
a, 740
occurrence, 741 structure, 740 b, 740
occurrence, 741 structure, 740
localization in plants, 735 Chlorosulfonic acid, 170 Cholla gum, 512 Chondroitin, 720
sulfate, 321, 719 isolation, 719 occurrence, 719 structure ,-719 Chondromucoid, 723
Chondrosamine, see D-Galactose, 2- amino-2-deoxy
Chondrosine, 321, 719 Chondrus crispus, 685
Chromatography, 603 adsorbents, 603 adsorption, 607 ion-exchange, 603
separation of borates, 171, 603 paper, 604
acidic substances, detection, 631, 635
as guide for cellulose column, 607 carbohydrates, solvent systems, 605 sugar phosphates, solvent systems,
605 procedures, 604 Rf, 605 Rx, 606
spray reagents, 606 Chromic acid, 361-2
induction of metachromasia (histo- chemical), 632
Cladinose, 78
Clerget method (reducing sugars), 612 Cinchona, 100, 278
Cionia intestinalis, 278 Citric acid cycle, 777 Cobalt sulfide (catalyst), 248 Cocarboxylase (TPP), 747 Cocositol, see scyllo-Inositol Cocos palm, 274
Coenzyme, A, 748
acetyl, 750 structure, 748 1,437
II, 438 III, 438
Coenzymes, 437, 745 flavin, 439 uridine type, 440
Coffee emulsin, glycosidase system, 590 Collagen, 722
Color reactions, 607-8 Compositae, 96
fructans, 683 Condurango tree, 277 Conduritol, 277
configuration, 283 Configuration,
absolute, 15
and optical activity, 9 anomeric center, 35
determination, conductivity in boric acid, 262
methods for modifying, see also Epi- merization, 125
relative, Fischer convention, 15 Conformations, pyranose rings, 40
O-acylglycosyl halides, 152 axial-equatorial substituents, 210 conformational stability, 210 D-glucose units in amylose, 676 glycosides, 210
Coniferin, 548
relation to lignin, 548 Coniferyl alcohol, 549
dehydrogenation, 549 Convoivulaceae, 99 Convoivulin, 99
Copper number, cellulose, 649 Cordycepose, 78
Cori ester, 182 Cornea,
keratosulfate, 722 polysaccharide, 712 Corn cobs, 85
Corn sirup unmixed, 93 Corn starch, 91
Corn sugar, see D-Glucose Cottonseed hulls, 85
Cottonseed meal, raffinose, 518 o-Coumaric acid, 549
Coumarin, 549 o-Coumarinic acid, 549
C.S.U., see Corn sirup, unmixed Crab shells, 468
Crocetin, 541
sexual influence, Chlamydomonas, 541 Crocin, 541
sugar moiety, 492 Crocus sativus, 541
pollen, 539
Crown-gall polysaccharide, 690 Cryptococcus neoformans, 632
Cucurbita moschata, 0-glucosidase, 588 Cuprammonium solution,
glycol cleavage, 218
optical rotation, polysaccharides, 655 rayon, 663
Cupric ion,
as oxidant, 365, 613 effect of pH, 364
in ammoniacal solution, 364
Cupric sulfate, phenylosotriazoles, 460 Cyanohydrin synthesis, for lengthening
carbon chain, 106 2-amino-2-deoxy sugars, 469 Cl labeling, 135
polysaccharides, determination of al- dehyde and ketone groups, 650 proportions of epimers, 107
quantitative determination of aldoses, 618
separation of epimers, 107
use in Rosanoff system of nomencla- ture, 22
steric effects, 106
Cycas revoluta, ß-glucosidase, 588 Cyclitols, see Inositols, Polyols (cyclic),
and individual compounds Cyclohexanehexols, see Inositols Cyclohexanepentols, see Inositols, mono-
deoxy, and individual com- pounds
Cyclohexanetetrols, see Inositols, di- deoxy
Cyclohexenetetrols, 277 Cymarin, 544
Cymarose, 544
Cysteine, reactions with sugars, 447 Cytidine, 425
di- and triphosphoric acids, 437 Cytosine, 425
D Dahlias, 96
f rue tans, 683
Dambonitol, see rai/o-Inositol, 1,3-di-O- methyl
Dambose, see raî/o-Inositol Dandelions, 96
Daviesia latifolia, 149
Dead Sea Apple, solanum alkaloids, 546 Decarboxylation, see also Ruff degrada-
tion,
polysaccharides, estimation of uronic acids, 648
Decitols, 257
Degradation, see Carbon chain shorten- ing
Dehydrogenation (catalytic), platinum and oxygen, 356, 613 sodium ferropyrophosphate, 357
Demissidin, see Dihydrosolagenin Dendroketose, 65
Dental decay, incidence, 809 D-enzyme, 705
Deoxyalditols, see also individual com- pounds. Note: ω-deoxy com- pounds listed under parent; all others under Deoxy and appro- priate configurational prefix, 226 2-Deoxy-D-arafo*no-hexitol, 266
1,5-anhydro, 382, 400 pyridine complex, 266 2-Deoxy-D-er?/i/iro-pentose, 87
biosynthesis, 88, 762 hydrazones, 80 nucleosides, 424 occurrence, 87 preparation, 87
aldol condensation, 114 Grignard reaction, 116 Schiff's reaction, 635 synthesis, 68
Deoxyhalogeno derivatives (Halogeno esters), see also O-Acylglycosyl halides, Glycosyl halides, 172, 376
2-Deoxy-D-Z2/£o-hexaric acid, 313 1-Deoxyketoses, preparation, 113 Deoxypentosenucleic acids (DNA), 87,
444
Feulgen reaction, 635 hydrolysis, 425, 430
acid, 444 alkali, 444 macrostructure, 444 structure, 434 synthesis, 445
' 'Transforming principle", 445 Deoxyribonuclease, 637
Deoxyribonucleic acids, see Deoxy- pentosenucleic acids
2-Deoxy-D-ribose, see 2-Deoxy-Ό-erythro- pentose
Deoxy-sq/Mo-inositol, see rm/o-Inositol, 2-deoxy
Deoxy sugars, see also individual sugars and "Note" under Deoxyaldi- tols
non-terminal, synthesis, 131 terminal, synthesis, 130 Detoxication, 599
Dextrans, see D-Glucans Dextrins, 677
cyclic, 681
synthesis (enzymic), 705 limit, 680
nutritional aspects, 783 Schardinger, see cyclic torréfaction, 677 Dextrose, see D-Glucose.
Diabetes mellitus, fructose utilization, 787
Dialdoses, preparation, 335
Diaminobenzene, see Phenylenediamine Diastases, see Amylases
Diazomethane, see also Diazomethane synthesis
methylation, 371
reactions with acyl halides, 111 synthesis of methyl aldonates, 162 xanthates, replacement with methyl
groups, 694
Diazomethane synthesis, for lengthen- ing carbon chain, 111
preparation of,
0-a.cetyl-keto sugars, 144 D-aZiro-heptulose, 112 2-deoxy aldonic lactones, 113 1-deoxy ketoses, 113
1-deoxy-l-halogenoketoses, 172 D- and L-fructose, 112
D- and L-graZacfo-heptulose, 112 ketoses, 111
L-manno-heptulose, 112 D- and L-sorbose, 112 Wolff rearrangement, 113 Diazouracil test, 502, 525, 608
Dicyclohexyl carbodiimide, synthesis of ADP and ATP, 436
Digallic acid, 160 Digitalis species, 543
D. lanata, 544 Digitoxose, 544
Diglycosylamines, see Glycosylamines Diheterolevulosan (=Difructose dian-
hydride), see D-Fructose deriv- atives
Dihydroconduritol, 283
Dihydro-D-glucal, see 2-Deoxy-D-ara- fono-hexitol, 1,5-anhy dro Dihydrosolagenin, 547
Dihydroxy acetone,
acceptors, 771 donors, 771
1-phosphate, aldolase catalyzed con- densations, 758
Diketoinositols, 290 Diketose dianhydrides, 224
p-Dimethylaminobenz aldehyde, Ehrlich test, 474, 730
Dimethyl sulfate, 369 glycoside formation, 202
Dinitrogen pentoxide, nitrating agent, 693
o-Dinitrobenzene, reducing sugar test, 608
2,5-Dinitrosalicylic acid,
polysaccharides, aldehyde and ketone groups, 649
Diphenylformazans, see Phenylhydra- zones
Diphosphopyridine nucleotide (DPN), 745
Dithiocarbonates, 159 polysaccharides, 694 Dithioacetals, see Thioacetals Dithioglycol, 226
6,8-Dithiooctanoic acid (a-lipoic acid), 747
Disulfones, see MacDonald-Fischer deg- radation
D, L nomenclature, 21
Disaccharides, see also Oligosaccharides and individual sugars, 351 Dodecitol, 258
Dogwood, 274
D.P. (= degree of polymerization), see Oligosaccharides, Polysaccha- rides
Drying oils, synthetic, 398 Dulcitol, see Galactitol Dyes, water soluble, 369 Dyera tree, 274
E Eberthella species, 620-1 Ehrlich reagent, 474
sialic acid, 729 Elasmobranch fish, 274 Electrophoresis, borates, 604
Elson and Morgan procedure (amino groups), 650
absorption maximum, 730
Emulsifiers, food, algin, 687 paper (sizes), 696
Emulsin, see also Enzymes and individ- ual emulsins, 563
structure of glycosides, oligosaccha- rides, 600
Enantiomorphs, 10
behavior toward symmetrical and asymmetrical reagents, 11 effect of enzymes, 581
resolution, 11, 90, 599 End-for-end inversion, 128 End-group assay, 650 Enzymes, 562, 733
activity, measurement, 571 standard substrates, 572 aldolase, general reaction, 758 amylases, 678
Aspergillus foetidus system, 667 Aspergillus niger,
cellulase, 665 cellobiase, 665 branching enzyme, 705 carboxydismutase, 755 cellulase, 663
dehydrogenases, TPN-specific, 769 deoxyribonuclease, 637
dextransucrase, 502 dipeptidase, 449
dissociation constant, 565-6 effect on activity,
configuration, 581 pH, 570
ring size, 581 temperature, 572 emulsins, 563
enzyme efficiency, 572
variation with changes in aglycon, 585-6
0-fructofuranosidase, 591 fungal, polygalacturonase, 671 a-galactosidase, 501
0-galactosidase, 496 galactosyl transferase, 498 galactowaldenase, 497, 775 ß-glucosaminidase, 473 glucose oxidase, 366, 619 glycosidases, mechanism, 566 hexokinase, sucrose synthesis, 522 hexose diphosphatase, 755
hexosidases, effect on pentosides, 577, 580
hyaluronidases, 718 histochemical use, 639 inhibition, 570
inulases, 683
invertase, preparation, 591 kinetic equations, 563 laminaranase, 688
levansucrase, as transfructosidase, 530 maltase, preparation, 594
malt diastase, histochemical use, 639 mammary tissue, 497
mechanism of action, 563 melibiase, 501
Michaelis constant, 565 mutarotation catalysis, 50 my rosin, 555
Neurospora crassa system, 471 pectases, 671
pectinases, 671
histochemical use, 640 P-enzyme, 682
phosphodiesterase, 442 phosphoglucomutase, 497, 776
synthesis of sucrose, 522 phosphoketopentoisomerase, 761 phosphopentoisomerase, 755 phosphopentokinase, 755 phosphoriboisomerase, 761 phosphorylase,
Pseudomonas saccharophila, 506 synthesis of
disaccharides, 524-8 polynucleotides, 445 sucrose, 521 polygalacturonâse, 671
Polysaccharides, nature of glyco- sidic linkage, 654
Primula officinalis and P. vulgaris systems, 551
Proteus vulgaris system, 516 R-enzyme, 683
reaction constant, effect of enzyme concentration, 572
ribonuclease, 637 pancreatic, 443 specificity,
aglycon, 582 sugar moiety, 581 spleen, 444
sucrose phosphorylase as transglyco- sidase, 528
role of arsenate, 530
Takadiastase,as transfructosidase, 532 transaldolase, 755, 771
transfructosidase, 530-2 transglycosidases, 568 transketolase, 755, 770, 772 uridyl transferase, 497
use in histochemical identification of carbohydrates, 638
"Wertigkeit", 572 xylose isomerase, 761 xylulose kinase, 761 Z-enzyme, 680
Epichitosamine, see D-Mannose, 2- amino-2-deoxy
Epiglucosamine, see D-Mannose, 2- amino-2-deoxy, and D-Altrose, 2-amino-2-deoxy
Epiisosaccharic acid, see D-Glucaric acid, 2,5-anhydro
Epilactose, see D-Mannose, 4-0-/3-D- galactopyranosyl
Epimelibiitol, 492
synthesis of planteobiose, 501 Epimelibiose, 491
occurrence, 492 preparation, 492 structure, 492
Epimerization, see also Glycals, syn- thesis; Waiden inversion, 125 aldonic acids,
alkali catalyzed, 125 tertiary amines, 126
sugars, see also Lobry de Bruyn- Alberda van Ekenstein trans- formation, 125
Epimers, 10
D-Epirhamnose, see D-Glucose, 6-deoxy Epoxides, see also Anhydro derivatives and individual compounds, 165, 376
formation, 165, 376-82
preparation of deoxy sugars, 132 scission, 166, 390
ammonolysis, 391 direction, 394 hydrogenolysis, 393 hydrolysis, 390 Eremostachys labiosa} 520
Ergot, 0-glucosidase, 588 Ericaceae, 547
Eriodictyol, 540 L-rhamnoside, 540 Ervum lens, 519
Erythraric acid, see also Tetraric acids, di-O-methyl, 427
1,4-Erythritan, see Erythritol, 1,4-an- hydro
Erythritol, 243 1,4-anhydro, 384
Ό-er y thro-L-galacto-Octitol, 256 D-erythro-2,3-Hexosone,
1,5-anhydro, 395 erythro-manno-Octitol, 257 O-erythro-L-manno-Octose, 110 Erythromycin, 465
L-Erythronic acid, 2-keto, total syn- thesis, 326
D-erythro-Pentulose (ü-ribulose), 86 hydrazones, 80
labeled, degradation, 624 occurrence, 86
5-phosphate, 183
Hexose Monophosphate Shunt scheme, 769
photochemical production, 753 diphosphate, photochemical produc-
tion, 753 preparation, 86 L-ert/iÄro-Pentulose,
D-glucosyl L-er^/iro-pentuloside, 524 synthesis, 526
D-Erythrose, 25 4-phosphate, 184
metabolism, 771 DL-Erythrose, synthesis, 105 D-erythro-i>-talo-Octitol, 257 Escherichia coli, 250, 445, 620-1
amylomaltase, 704 ß-glucuronidase, 596 Escherichia freundi, 250 Esparto grass, xylan, 668 Esterification, 139
catalysts, 139
hydroxyl groups, order of reactivity, 139
influence of ring structure, 139 polysaccharides, 691
Esters, 138-9 acyclic, 139
aldonates, 162 borates, 171
carbanilates, 160, 648 carbonates, 158, 203 cyclic, 139
diphenates, 401 ethoxy formates, 158
formation, see Esterification and in- dividual sugars
hydrolysis, 139 methanesulfonates, 163 methoxyformates, 158 naturally occurring, 138 nitrates, 168
preparation of anhydro derivatives, 376
partial, 158 phosphates, 138, 172
preparation in sulfuric acid, 163 propionates, 602
distillation, 602 sulfates, 170 sulfonates, 163, 376
preparation of anhydro derivatives, 376
surface active, 138, 163 p-toluenesulfonates, 163
preparation of,
anhydro derivatives, 376 unsaturated compounds, 164 replacement, 397
xant hates, 159 Ethanedithiol, 226
Ethanol, production by glycolysis, 767 Ethanolamine, 476
Ethanethiolysis, 201
Etherification, see O-Alkylation, 0- Methylation, and individual compounds
Ethers, 367-99 allyl, 369
benzyl, hydrogenolysis, 368
cyclic, see Anhydro derivatives, Epox- ides, and individual compounds hydrolysis, 368
industrial importance, 368 occurrence, 367
preparation, 367 triphenylmethyl, 368 Ethoxyformates, 158 Ethyl chloroformate, 158
Ethylidene derivatives, 235 formation, rules, 231
synthesis from acetylene, 235 Eulota peliomphala, 590 Euonymus atropurpureus, 252 Euphorbia pilulifera L., 271 European palm, 275 Explosives,
cellulose trinitrate (gun cotton), 693 starch trinitrate, 693
F
Fehling test (reducing sugars), 608 glycofuranosiduronic 3,6-lactones, 325 -Soxhlet, quantitative method, 613 Fermentation, 766, see also Emulsins,
Enzymes, Yeast
quantitative determination of sugars, 619
microorganisms and substrates, 620-1
role of phosphates, 173
Ferricyanide, see also Hagedorn-Jensen method,
polysaccharides, determination of al- dehyde and ketone groups, 649 reducing sugars, 616
Feulgen reaction, 635 Films,
amylose acetate, 678 cellulose acetate, 692 polysaccharides, 643
Fischer convention, projection formulas, Fischer synthesis, glycosides, 191 9
conditions affecting isomerism, 191 Fistulina hepatica, 244
Flavanol glycosides, 538
sexual influences, Chlamydomonas, 511 Flavanols, quercitin, 539
Flavanones, 538 hesperitin, 540
Flavinadenine dinucleotide (FAD), 440, 746-7
Flavin mononucleotide, see Riboflavin 5-phosphate
Flavones, 538 Flaxseed mucilage, 90 Florideae species, 554 Floridoside, 554
Folin-Malmros method (reducing sug- ars), 616
Folin-Wu method (reducing sugars), 615 Formal derivatives, see Méthylène de-
rivatives Formaldehyde,
acetals, see Méthylène derivatives and individual compounds
polymerization, 103
quantitative estimation, 350 Formamide,
gelatinization of polysaccharides, 692 Formates,
formation during glycol cleavage, 350 Formic acid,
action on anhydroalditols, 396 quantitative estimation, 350 Formose, 103
Formulas,
Fischer-Tollens, 9, 37 Haworth, 38
Sachse (Reeves), 40 Forsythia pollen, lactose, 495 Forsythia suspensa, 554 Fraxinus ornus, 249, 515, 519 Fraxinus rotundifolia, 249, 515 Friedel-Crafts reaction, 116
C-aryl compounds, 117 Frog spawn, 88
Fructans, 683
/8-Fructofuranosidase, 562
activity in newborn mammals, 785 chemical composition, 575
commercial utilization, 591 preparation, 591
transfructosylation, 707 yeast (invertase),
kinetics of hydrolysis, 592 specificity, 592
D -Fruc t of uranoside,
a-D-glucopyranosyl, see Sucrose oligosaccharides, 513, 517-19, 531-2 /8-Ä-Fructosidase, see 0-Fructofurano-
sidase D-Fructose, 95
assimilation, 97 blood level, 786 1,6-labeled, 136
degradation, 624 labeled, uniformly, 135
metabolism, 786
insulin independence, 787 nutritional aspects, 786 occurrence, 95
preparation, 96 structure, 7 synthesis,
from three-carbon fragments, 114 total, 103
utilization, 97, 786 by spermatozoa, 786 in diabetes mellitus, 787
in parenchymal hepatic disease, 787 D-Fructose derivatives,
1,3,4,6-tetra-O-acetyl, 156 tetra-O-acetyl-l-deoxy-l-diazo-fcefo,
145
penta-O-acetyl-fceio, 145 3-O-alkyl,
alkaline hydrolysis, 509 iV-alkyl-D-fructosylamines,
conversion to aldose derivatives, 423 1-amino-l-deoxy, 461
1,3,4,5-tetra-O-benzoyl, 148 1,3,4,6-tetra-O-benzoyl, 148 penta-O-benzoyl-fcefo, 148 1-dibenzylamino-l-deoxy, 423 calcium fructosate (or levulate), 96 l,2:4,5-dicarbonate, 159
6-deoxy, 524
enzymic synthesis, 759
6-deoxy-D-fructoside, D-glucosyl, 524 1-deoxy-l-p-toluino, 422
quinoxaline formation, 414 difructose dianhydrides, 224
6-O-a-D-galactopyranosyl, see Plan- teobiose
4-O-jS-D-galactosyl, 481
3-O-a-D-glucopyranosyl, see Turanose 5-O-a-D-glucopyranosyl, 534
hydrazones, 80
1,2 and 2,3-O-isopropylidene, 239 di-O-isopropylidene, 238-9 3-O-methyl, 238
1,3,4,5-tetra-O-methyl, 238 6-phosphate, 181
Hexose Monophosphate Shunt scheme, 772
1,6-diphosphate, 181 Fruit sugar, see D-Fructose
L-Fucitol, see Galactitol, 6-Deoxy-L-,
D- or L-Fucose, see D- or L-Galactose, 6-deoxy,
Fucus, 99
2-Furaldehyde, see also 2-Furylidene derivatives, 57
determination, 619
formation, mechanism, 58-9 5-halogenomethyl, 58 5-hydroxymethyl, 57
Furanose, see also individual sugars, 33 Furanosides, see also Glycosides and
individual sugars, 33 from carbonates, 203 Furfural, see 2-Furaldehyde Furocoumarin, 550
Furocoumarinic acid, 549
2-Furoic acid, 5-hydroxymethyl, 468 2-Furylidene derivatives, 235
G Galactans, 716
agar, 685 carageenan, 686
in pectic substances, 671 synthesis, 707
/S-Galactan, see Stachyose
€-Galactan, 510 Galactaric acid, 80, 313
2-deoxy, see 2-Deoxy-D-Jt/zo-hexaric acid
Galactinol, see myo-Inositol, l-0-(a-D- galactosyl)
Galactitol, 251 1,5-anhydro-D-, 378 l,5:3,6-dianhydro-D-, 378 6-deoxy-L-, 134
biochemical oxidation, 134 nutritional aspects, 797 synthesis, 252
total, 106 D-Galactofuranoside,
ethyl <*, 200 ethyl ß, 156, 200 Galactomannans, 684
D-Galactomethylose, see D-Galactose, 6-deoxy
D-Galactopyranoside, ethyl a, 20
2-glycerol, uniformly labeled, 135 methyl 3,4-anhydro-|8, 391
methyl 3,6-anhydro, 388
conversion to dimethyl acetal, 388 Galactosamine, see D-Galactose deriva-
tives, 2-amino-2-deoxy D-Galactose, 88
absorption, 789 biosynthesis, 89
cataractogenesis, 89, 792 fermentation, 90 from D-sorbose, 62 labeled, uniformly, 135 nutritional aspects, 789
cataractogenic action, 89, 792 galactosemia, 794
occurrence, 88-9 preparation, 89
quantitative determination, fermenta- tion method, 621
utilization, effect of dietary fat, 789 D-Galactose derivatives,
2,3,5,6-tetra-O-acetyl-, 156 2,3,4,6-tetra-O-acetyl-a-D-galactosyl
trimethyl ammonium bromide, 222
penta,-0-a,cety\-aldehydo, 157 1,1-dichloro-l-deoxy, 157 penta-O-acetyl-D-galactoseptanose,
146
2-amino-2-deoxy, 380, 465 iV-acetyl, 719
analysis in presence of 2-amino-2- deoxy-D-glucose, 475
3 - 0 - G 8 - D - glucopyranosyluronic acid), 321, 719
nutritional aspects, 797 occurrence, 466 preparation, 469 synthesis, 467
1,6 - anhydro - a - D - galactofuranose, 221-2
resistance to periodate, 350
1,6-anhydro-/8-D-galactopyranose, 221 l,2:3,4-dicarbonate, 159
6-deoxy (D-fucose), 99 6-deoxy-L-mannosyl, 511 diethyl dithioacetal, 200 3-0-0-D-galactopyranosyl, 510 4-O-a-D-galactopyranosyl, 510 6-O-D-galactopyranosyl, 511, 534 hydrazones, 80
1,2:3,4-di-O-isopropylidene-a, 237 6-O-chloroformyl, 159
2,3,4,5-tetra-O-methyl, 496
N - phenyl - ß - D - galactosylamine · carbon tetrachloride, 411 1-phosphate, 174
conversion to D-glucose 1-phosphate, 775
DL-Galactose, 90 L-Galactose, 90
3,6-anhydro, 4- O-0-D-galactopyrano- syl, 511
6-deoxy (L-fucose), 98 hydrazones, 81 occurrence, 98 preparation, 99 occurrence, 90 preparation, 90, 713 Galactosemia, 90, 794 a-Galactosidase,
coffee emulsin, 590
melibiase, bottom yeast, 593
various sources, enzymic action com- pared, 594
ß-Galactosidase, alfalfa emulsin, 590
aglycon specificity, 591 almond emulsin, 577 sweet-almond emulsin, 591
aglycon specificity, 591 types, 590
D-Galactoside, 2-glycerol-a, 554
hydrolysis, enzymic, effect of agly- con, 585
umbilicin, 243
Galactowaldenase, 90, 440 Galactotransferase, 707 Galactotriose, 520 Galacturonans, 671
methyl ester, 671 pectic acid, 671
D-Galacturonate, methyl tetra-O-ace- ty\-aldehydo, 229
Gallic acid, 160 Gallotannins, 160 Galtose, 63
Gangliosides, 88, 560 Garlic, scorodose, 520 Gaucher's disease, 560 Gelation, fruit juice, 670
Gelidium amansii, 511 agar, 685
Gentian, 513 Gentianose, 513 Gentiobiose, 492
octa-O-acetyl, anomerization, 495 amygdalin, 550
o-chlorophenyl ß-gentiobioside, 599 in "hydrol", 493
occurrence, 492 preparation, 492 structure, 493 synthesis, 493 D-Glucal, 400
tri-O-acetyl, 172, 382 isomerization, 402 reactions, 399-402
Glucamine, see D-Glucitol, 1-amino-l- deoxy
D-Glucans, 688 dextrans, 688
clinical use, plasma volume ex- pander, 688
antigenic action, 689 fate, 689
preparation, 689
Leuconostoc mesenteroides, 688 structures, 689
synthesis, 706 laminar an, 688 mycodextran, 706 D-Glucaric acid, 80, 313
2,5-anhydro, 379
"Glucidamins", 724 D-Glucitol (sorbitol), 247
1-amino-l -deoxy, 475 2-amino-2-deoxy, 476 1,4-anhydro, 385-6
3,5-0-benzylidene-6-chloro- 6-deoxy, 390
1,5-anhydro, 382-3
2,5 - anhydro - 1 , 6 - d i - O - benzoyl, 387
l,4:3,6-dianhydro, 164, 385 l,5:3,6-dianhydro, 378 1-deoxy-l-thio, 248
6-O-a-D-galactopyranosyl, 501 1,3:2,4:5,6-tri-O-methylene, 232 nutritional aspects, 797
occurrence, 247
pyridine complex, 266 synthesis, 248 DL-Glucitol, 249 L-Glucitol, 248 D-Glucodecitol, 257 D-Glucofuranoside,
methyl a, 193 5,6-carbonate, 203 methyl ß, 193
3,6-anhydro, 168
"a-Glucoheptulitol", 254 D-grZwco-Heptulose, 62
D-Glucomethylose, see D-Glucose, 6- deoxy
D-Gluconic acid, 340 2-amino-2-deoxy, 379, 466 4-0-/3-D-galactopyranosyl, 496 4-O-a-D-glucopyranosyl, 499 tri-O-isopropylidene, 238 2-keto, 239
occurrence, 326 1,4-lactone, 340
tetra-O-methyl, 496, 499 2-O-methyl, 238
2,3,4,5-tetra-O-methyl, 500 6-phosphate, 86
enzymic oxidation, 86, 183
Hexose Monophosphate Shunt scheme, 769
polyester, 162
utilization, biochemical, 302 D-Glucononitol, 257
D-Glucopyranoseen, tetra-O-acetyl-1,2, 382
D-Glucopyranoside,
benzyl 2 - carbobenzyloxamino - 2 - deoxy-a, 466
jS-D-fructofuranosyl-a, see Sucrose 0-D-fructofuranosyl-(2 —> l)-0-D-fruc-
tofuranosyl-(2 -* 1), 707 0-a-D-galactopyranosyl-(l —► 6) -0-/3-
D-fructofuranosyl-(2 —> l)-a, 516 1-O-a-D-glucopyranosyl-a, see Treha-
lose
0-a-D-glucopyranosyl-(l —► 3)-/3-D- fructofuranosyl-(2 —> l)-a, 515 methyl,
a, 213
3,4,6-tri-O-acetyl, 204
tri - 0 - acetyl - 3 - O - p - tolylsul- fonyl, 168
3,6-anhydro-a, 170 3,6-anhydro-/S, 376 4,6-dichloro-4,6-dideoxy-a,
2,3-disulfate, 172 4,6-0-(2-furylidene)-a, 236 3-keto, 328
6-nitrate, alkaline elimination, 170 salicyl 6-0-benzoyl-/3, 149
theobromine tetra-0-acety 1-/3, 206 iS-D-Glucopyranosiduronase, see /3-Glu-
curonidases
D- or L-Glucosamine, see D- or L-Glucose, 2-amino-2-deoxy
Glucosaminic acid, see D-Gluconic acid, 2-amino-2-deoxy
Glucosaminol, see D-Glucitol, 2-amino- 2-deoxy
Glucose (industrial) = Corn Sirup Un- mixed, 93
D-Glucose, 91
blood glucose level, 801 effect on urge to eat, 801 configuration, 13
1-deuterio, 62
glucose-water system, phase diagram, 92
3,4-labeled, 135, 622 6-labeled, 136
labeled, uniformly, 135 mutarotation, 50, 53 nutritional aspects, 785 occurrence, 91
preparation, 91
quantitative estimation with D -glu- cose oxidase, 619
ring formulations, 30 structure, 7
synthesis, total, 103
synthesis of rayo-inositol, 272 L-Glucose, 78
D-Glucose derivatives, 3,4,6-tri-O-acetyl, 156 l,2,3,4-tetra-0-acetyl-/3, 158 2,3,4,6-tetra-O-acetyl, 156, 158 penta-O-acetyl, 140-1
anomerization, 154 penta-O-acetyl -aldehydo, 143
1,3,4,6 - tetra - O - acetyl - 2 - O - (trichloroacetyl)-a, 157
6-N-alanino-6-deoxy, 448 2-amino-2-deoxy, 378, 465
iV-acyl derivatives, 448
analysis in presence of 2-amino-2- deoxygalactose, 475
fermentation, 473
3 - O - 03 - D - glucopyranosyluronic acid), 319
nutritional aspects, 797 occurrence, 466 phenylosazone, 466 preparation, 468 phosphorylation, 473 structure, 466
6 - amino - 6 - deoxy - 1,2 - O - iso- propylidene, 381
1,2-anhydro,
3,4,6-tri-O-acetyl, 157, 204, 219, 221 1,6-anhydro, 221
preparation of cellobiose, 491 scission by phosphorus pentabro-
mide, 172 6-O-a-L-arabinosyl, 510 3-O-benzoyl, 158 6-O-benzoyl, 138, 149 3,5,6-tri-O-benzoyl, 158
3,4,5,6-tetra-0-benzoyl-aZde%do, 158 4,6 - O - benzylidene -1,2 - O - isopro-
pylidene, 234
3,5 - O - benzylidene -1,2 - O - isopro- pylidene, 234
5,6-carbonate, 203
6-carbonate, bis (1,2,3,4-tetra-O-ace- tyl), 159
l,2:5,6-dicarbonate, 159 6-deoxy, 99
5-0-/3-D-glucosyl, 485 occurrence, 100 phenylosazone, 81 preparation, 100
6-0-(6-deoxy-/3-L-mannosyl), 512 6-deoxy-6-nitro, 273
diethyl dithioacetal, 143 penta-O-acetyl, 143 6-O-D-galactosyl, 534
4-0-/3-D-galactopyranosyl, see Lactose 6-O-a-D-galactopyranosyl, see Melibi-
ose
0-D-galactosyl-(l -♦ 6)-0-D-galacto- syl-(l -> 4), 534
0-D-galactosyl-(l —* 6)-0-D-galacto- s y l - ( l - > 6 ) , 5 3 4
l-O-galloyl-0, 161 penta-O-galloyl, 160 2-0-/3-D-glucopyranosyl, 511 3-0-/3-D-glucopyranosyl, 511
4-O-a-D-glucopyranosyl, see Maltose 4-0-j3-D-glucopyranosyl, see Cellobiose 6-O-a-D-glucopyranosyl, see Isomal-
tose
6-O-jS-D-glucopyranosyl, see Gentiobi- ose
D-glucopyranosyl bromide,
3,4,6 - tri - 0 - acetyl - 2 - bromo - 2 - deoxy, 172
tetra-O-acyl, 150
tri-0-acetyl-6-bromo-6-deoxy, 172 D-glucopyranosyl chloride,
3,4,6 - tri - 0 - acetyl - 2 - 0 - (tri- chloroacetyl)-/3, 156, 158 tetra-O-acyl, 150
tetrasulfate, 170
tetra-O-p-tolylsulfonyl, 164 0-a-D-glucopyranosyl-(l —» 4)-0-a-D-
glucopyranosyl-(l —> 4), 513 0-a-D-glucopyranosyl-(l —> 6)-0-a-D-
glucopyranosyl-(l —> 4), see Panose
0-a-D-glucopyranosyl-(l —> 6 ) - 0 - « - D - glucopyranosyl-(l - * 6), 520 di-D-glucopyranosyl disulfide, octa-O-
acetyl, 383
D -glue opy r anosy luridine -5 '-py r ophos - phoric acid, 775
iV-D-glucosylalanine, 447 iV-D-glucosylcytosine, 417
D-glucosyl ethyl thiohydantoate, tetra-O-acetyl, 416
D-glucosyl fluoride, 152
JV-D-glucosylglycine ethyl ester, 447 D-glucosylhydantoin, 416
D-glucosylisothiocyanate, tetra-O-ace- tyl, 416
iV-D-glucosylnicotinamide, tetra-O- acetyl, 418
iV-D-glucosylsarcosine amide, 447 N-D-glucosylurea, 415
phenylosazone formation, 415 reducing power, 415
1-O-glycylglucose, 448 hydrazones, 80
1,2-0-isopropylidene-a;-D-glucof u- ranose, 237
5,6-carbonate, 203 3,5,6-tri-O-methyl, 238 3,5-orthoborate, 171
1,2:5,6-di-O-isopropylidene-a-D-glu- cofuranose, 237
3-O-p-tolylsulfonyl, 165
1,2:3,5-di-0-isopropylidene-û!-D-glu- copyranose, 238
pentamethacrylate, 163 2-O-methyl, 694 3-O-methyl, 238
2,3,5,6-tetra-O-methyl, 212,386 2,3,4,6-tetra-O-methyl, 62, 212
transformation in alkaline deute- rium oxide, 62
mutarotation, 55
penta-O-methyl aldehydo, 142 3-O-methylsulfonyl, 88
degradation to 2-deoxy pentose, 88 pentanitrate, 169
iV-phenyl-D-glucosylamine, 409 1-phosphate, 174-5, 182
conversion to D-glucose 6-phosphate, 776
6-phosphate, 182 3-sulfate, 170
l-thio-/3-D-glucopyranose, tetra-O-ace- tyl, 383
uridine diphosphate, 775 vicine, 425
6-O-a-D-xylosyl, 483 6-0-/3-D-xylosyl, 483, 512 L-Glucose derivatives,
2-deoxy-2-iV-methylamino, 78, 465, 558 6-deoxy-3-O-methyl, 78
Glucose dehydrogenase, 366, 619 1,2-D-Glucoseen, 403
tetra-O-acetyl, 403 3,4-D-Glucoseen, 404
A-4,5-D-Glucoseenuronic acid, 719 Glucose oxidase, 366, 619 a-Glucosidase,
almond emulsin, 577 maltase, 593
industrial value, 563 preparation, 594
yeast, aglycon specificity, 595 j8-Glucosidase,
almond emulsin, 595
bottom yeast, 593
carbohydrate component, 574 composition, 573
coffee emulsin, 590
comparison, various sources, 578, 580 enzymic activity, effect of
anions, 573 dialysis, 574 formaldehyde, 574 pH, 574
substitution in sugar moiety, 579,580 sugar ring size, 581
hydrolysis of 0-glucosides, activation energies, 573
occurrence, 577, 587 specificity, 579
aglycon, 582, 588, 595 sugar moiety (rule), 581
sweet almond, dissociation constants, 566
Z-enzyme, 680 D-Glucosides,
2-chloroethyl ß, in vivo synthesis, 599 trichloroethyl ß, in vivo synthesis, 599 enzymic synthesis, 598
hydrolysis,
acid, compared with enzymic, 587 enzymic, effect of
branching of carbon chain, 583 chain length, 582
structural changes in aglycon, 585 substitution in aglycon, 584, 586 hydroquinone ß} 547
3-hydroxyindole ß, 543 o-hydroxymethylphenyl ß, 547
6-O-benzoyl, 548 p-methyoxyphenyl ßf 547
methyl ß, naturally occurring, 554 natural, anomeric configuration, 554 D-Glucosiduronic acids,
detoxification, 599 oleanolic acid, 546
D-Glucosone, see D-ara&ino-Hexosone D-Glucurone, see D-Glucuronic 3,6-lac-
tone
D-Glucuronic acid, 315 2-amino-2-deoxy-, 466 1-O-benzoyl, 149 biogenesis, 317
isonicotinyl hydrazone, 325 1,2-O-isopropylidene, 136, 317 6-labeled, 136
4-O-methyl, 83, 315 1-phosphate, 324
rheumatic diseases, use in, 317 D-Glucuronic 3,6-lactone, 317
1,2-O-isopropylidene, reduction, 136 6-labeled, 136, 317
methyl furanosides, 193 0-Glucuronidases, 596
almond emulsin, 577 biological function, 597 clinical use, 597 occurrence, 596 Glutose, 63 Glycals, 3, 399
halogen addition, 401 hydration, 400
hydrogen halide addition, 401 hydroxylation, 400
ozonolysis, 123, 482
phenanthraquinone addition, 401 preparation, 399
properties, 400 rearrangement, 401 synthesis of,
aminodeoxy sugars, 470 cellobiose, 484
2-deoxyaldoses, 131 glycosides, 202 lactose, 484, 497 monosaccharides, 127
Glycamines, see Alditols, 1-amino-l- deoxy
Glycans, see Polysaccharides Glycaric acids, see Aldaric acids Glyceraldehyde, see Glycerose Glyceraric acid, 311
D-Glyeerie acid 3-phosphate, 753 Ώ-glycero-O-galacto-Heptitol, 101, 253 D -glycero-D -galacto-Heptose, 62
utilization, 101
O-glycero-O-gluco-Heptitol, 255, 258 D-grZî/cero-jS-D-^wZo-Heptopyranose, 1,7-
anhydro, 225 Glycerol, from sorbitol, 248 D-Glycerose, 22
dimers, 69 3-phosphate, 770 preparation, 124 Rosanoff convention, 21 L-Glycerose, 124
D-glycero-O-talo-Keptitol, 102, 253 Glycitols, see Alditols
Glycine,
iV-D-glucosyl, ethyl ester, 447 Glycine hispida, 0-glucosidase, 588 Glycogens, 714
glycolysis, 767 histochemistry, 638 isolation, 714 occurrence, 714
phyto, see also Amylopectin, 714 structure, 714
Glycolaldehyde, 69
"active", 770 Glycol cleavage, 346
anhydroalditols, 396
anomalous resistance, 217, 350 disaccharides, 351
effect of structure, configuration, 347 formyl esters, formation, 217, 350 glycosides, 215
kinetics, 348 mechanism, 347-8
"overoxidation",· 216 properties of reagents, 346 rate, factors determining, 217 reagents, 347
Glycolipids, 560, 729 Glycolipoproteins, 729 Glycolysis, 766
Embden-Meyerhof-Parnas scheme, 767 Hexose Monophosphate Shunt scheme,
769, 773 other pathways,
Leuconostoc mesenteroides, 774 Pseudomonas saccharophila, 774 principal pathways, relative impor-
tance, 773 role of phosphates, 173
Glyconic acids, lactones, see Aldonic Glycoproteins, 711, 722-9
blood serum, 725 nature of proteins, 724 urine, 726
Glycosamines, see Aminodeoxy sugars Glycosans, see Anhydro sugars, acetal
type
Glycoses, see Saccharides, Sugars Glycose ammonias, see Glycosylamines Glycoseens, 399, 402
1,2-glycoseens, 382 hydroxylation, 403 preparation, 402, 418 reduction, 382
5,6-Hexoseens, 404 preparation of osones, 335 Glycosidases, 562-601
classification, 562 composition, 573 mechanism, 566-70
Glycosides, see also Oligosaccharides, Polysaccharides and individual sugars, 3, 189
adrenal corticosteroid, 545
aglycons related to phenanthrene, 543-7
alkali sensitive, 205 animal, 560
anomeric configuration, 218 determination, 219 anomerization, 204
effect of aglycon, 204 mechanism, 205 anthocyanidin, 538 aryl, 547
action of alkali, 221 diazonium coupling, 450
formation of anhydro sugars, acetal type, 221
synthesis, 190, 197 cardiac, 543
hydrolysis, 544
influence of sugar moiety, 545 strophanthidin, 545
sugars, table, 552 carotenoid, 538 cyanogenetic, 550
conformational analysis, 209-10 cyclohexyl, 208
flavanol, 538
from 1,2-anhydro sugars, 204 function in plants, 536 furanosides,
from thioacetals, 200
"gamma", 197 heterosides, 480 holosides, 480 hydrogenolysis, 207 hydrolysis,
acid, 208
acid and enzymic, rates compared, 587
alkaline, 205
energy of activation, acid, enzyme, 568, 573
