769, 773 other pathways,
O- acylglycosyl halides, 383 epoxides, hydrogenolysis, 393
Lobry de Bruyn-Alberda van Eksnstein transformation, 60-2
mechanism, 61 Loco weed, 270 Lucerne, see Alfalfa Lupeose, see Stachyose Lupinus lutens, 519 L-Lyxoflavin, 425 L-Lyxose, 24
5-deoxy-3-C-formyl, 558 nucleoside-like compounds, 425
M
MacDonald-Fischer degradation, 121 Macrocystis pyrifera, 687
Madagascar manna, 251 Madder, 551
glycosides, 552 Madder root, 512
Magnesium oxide, catalytic hydrolysis of nucleic acids, 425
Main's "pot method", reducing sugars, L-Malic acid, 311 615
photochemical production, 748 Malic enzyme, 748
Maltase, see a-Glucosidase, yeast Maltobionic acid, 499
Maltose, 498 absorption, 783
conversion to isomaltose, 534 identification, 498
nutritional aspects, 784 occurrence, 498 preparation, 499 properties, 498
structure, 499
aldobionic acid method, 499 anomeric configuration, 500 methylation method, 499
Maltotetraose and higher oligosaccha-rides, 514
Maltotriose, 513 identification, 514 occurrence, 514 properties, 513 structure, 514
"Maltulose", from glycogen, 715 Malvus species, 500
Mammary tissue enzymes, 497 Manna,
Douglas fir, 516 larch, 516 Virginia pine, 516 Manna ash, 249 Mannans, 669
salep, 670
vegetable ivory, 669 D-Mannaric acid, 313
2,5-anhydro, 379 Mandelonitrile,
amygdalin, 550 prunasin, 551 sambunigrin, 551
Manneotetrose, see Stachyose Manninositose, 272
Manninotriose, 514 from stachyose, 519 identification, 515 occurrence, 515 preparation, 515 properties, 515 structure, 515 D-Mannitol, 249
1,4-anhydro, 385 1,5-anhydro, 382
l,4:3,6-dianhydro, 164, 385
conversion to dichlorodideoxy com-pound, 396
2,5-O-methylene, 390 l,5:3,6-dianhydro, 385 borates, 263
boric acid, effect on acidity, 263 1-deoxy-l-p-toluino, 422 1-O-a-D-galactopyranosyl, 501 nutritional aspects, 796
occurrence, 249 synthesis, 249 DL-Mannitol, 250
synthesis, total, 250 L-Mannitol, 250
D-Mannofuranuronic 3,6-lactone, 324 Ό-manno -Heptulose, 101
hexa-O-acetyl-a, 81 hydrazones, 81
nutritional aspects, 796 occurrence, 101 preparation, 101 utilization, 101
D-Mannoketoheptose, see D-mawno-Hep-tulose
L-Mannomethylose, see L-Mannose, 6-deoxy
D-Mannonic acid, 2,5-anhydro, 379 1,4-lactone, 250 D-Mannopyranoside,
ethyl l-thio-jS, 201 methyl,
a, ethanethiolysis, 201 ß, ethanethiolysis, 201
2,3:4,6-di-0-isopropylidene, 237 D-Mannose, 94
configuration, 20 occurrence, 94
nutritional aspects, 788 preparation, 94 synthesis, total, 103 utilization, 95 D-Mannose derivatives,
3,4,6-tri-O-acetyl-0, l,2(methyl ortho-acetate), 196
2-amino-2-deoxy, 380, 469 2,5-anhydro, 378, 468
1,6-anhydro-0-D-mannopyranose, 221 calcium chloride, 95
2,3:5,6-dicarbonate, 159
4-0-/3-D-galactopyranosyl, 484, 497 6-O-a-D-galactopyranosyl, see
Meli-biose hydrazones, 80
2,3:5,6-di-0-isopropylidene, 237 D-mannofuranosyl chloride,
2,3:5,6-dicarbonate, 159 4-0-/3-D-mannopyranosyl, 511 sî/m-D-mannosylguanosine
5'-pyro-phosphoric acid, 95
D-mannosylstreptomycin, 558 6-diphenylphosphate,
2,3,4-tri-0-acetyl-a, 184 1-phosphate, 174 1,6-diphosphate, 184 D-Mannoside,
D-glyceric acid, naturally occurring, 554
L-Mannose, 6-deoxy, (L-rhamnose) 100 4-O-D-glucopyranosyl, 511
hydrazones, 81 3-O-methyl, 552 nutritional aspects, 796 occurrence, 100 phenylosazone, 81 preparation, 100 quercitrin, 539 a-Mannosidase,
alfalfa emulsin, 577, 590 bottom yeast, 593 coffee emulsin, 590 Mannosylstreptomycin, 558 D-Mannuronan, alginic acid, 687
Mannurone, see D-Mannofuranuronic 3,6-lactone
Maple sap, 502
Matezodambose, see D-Inositol Medicago sativa, 590
Meerwein-Pondorff reaction, 292 Melampyrum nemorosum, 252 Melanoidin reaction, 406, 446
mechanism, 447 Melezitose, 515
identification, 516 nutritional aspects, 795 occurrence, 516 preparation, 516 properties, 516 structure, 516 turanose, 508
Melibiase, see a-Galactosidase, bottom yeast
Melibiitol, 501 Melibiose, 500
from raffinose, 517 identification, 500 nutritional aspects, 796 occurrence, 500 preparation, 500 properties, 500 structure, 500
aldobionic acid method, 500 methylation method, 500 synthesis, 483, 501
Koenigs-Knorr, 501 Melitriose, see Raffinose Melibiulose, see Planteobiose Menadione, 757
Mercaptals, see Thioacetals and indi-vidual sugars
Mereaptans, see Thiols and individual compounds
Mercaptolysis, 201 structure studies, 202 Mercerization, cellulose, 663 Mercuric acetate,
Koenigs-Knorr synthesis, a-anomers, 483
oligosaccharides, synthesis, 483 Mercuric oxide,
2-amino-2-deoxyaldoses, oxidation, 472 meso Compounds, 11
Mesothelioma polysaccharide, 712 Mesoxaldehyde bis (phenylhydrazone),
623
Mesquite gum, 83, 88
Mesylates, see Methanesulfonates Metachromasia, 626, 631-3
abolition by ''methylation", 632 effect of polymerization, 632
induction in neutral polysaccharides, Metasaccharinic acid, 68 632
degradation, 87
2-deoxy-2-er2/iÄro-pentose, 87 Methacrylic anhydride, 163 Methanesulfonates, 163
replacement, secondary, 172 Methose, 103
Methoxyformates, 158 O-Methylation,
alkyl iodide-silver oxide method, 370 alkyl iodide-sodium alkoxide method,
370
determination of glycoside structure, 31
diazomethane, 371
dimethylsulfate method, 369 of
acids (esterification), 632 disaccharides, 487
glycosides, 212 polysaccharides, 653
branch-unit assay, 651 end-group assay, 651
estimation of hydroxyl groups, 648
nature of glycosidic linkages, 653 resistant hydroxyl groups, 696 partial, 370
thallous alkoxide method, 371 Methyl chloroformate, 158 O-Methyl determination, 650
Méthylène blue, reducing sugar test, 608 Méthylène derivatives, see also
indi-vidual compounds, 232 acetolysis, 232
formation, 232 rules, 231 structure, 232 Methyl ethers,
degradation, oxidative, 214 distillation, 602
Methylfurfural, see 2-Furaldehyde, 5-methyl
Michaelis constant, 565 Michael synthesis, 190, 197
Microorganisms, identification, 622 Mildew, 664
Milk sugar, see Lactose Mistletoe berries, 271
Molar frictional coefficient, 657 Molecular weight determination,
poly-mers, 655
osmotic pressure method, 656 sedimentation equilibrium procedure,
657
sedimentation velocity procedure, 656 viscometric method, 694
Molisch test, 607
Molybdic acid, molybdates, complexes, 262
effect on rotation, 259 Monilia yeast, 86
Monosaccharides, see also Aldoses, Ketoses, Sugars, and individual compounds, 2
aldehydo,
penta-O-acetyl, mutarotation, 145 Schiff's reaction, 144
biosynthesis, 758-62
branched chain, naturally occurring, 78
classification, 4
configuration, 24-5 use of alditols, 258 identification, 602, 652, 713 interconversion, biochemical, 775 keto, Schiff's reaction, 144
naturally occurring, 80 structure, 258
Mountain ash berry, 98, 132 Mucic acid, see Galactaric acid Mucicarmine stain, 635
Mucihematein stain, 635 Mucin, 711
funis, 723 gastric, 724
isolation, 724 polysaccharides, 725 histochemistry, 627
Alcian Blue 8GS, 634 dialyzed iron, binding, 633 salivary, 726
composition, 727 isolation, 726 synovial fluid, 723 Mucoids,
blood serum, 725 composition, 725 ovomucoid, 728 urinary, 726
composition, 726 Mucoitin sulfates, 712 Mucoproteins, 722-9
proteins, nature, 724 Mucosin, 717
Mucus, 711 Mushrooms, 425
Mushroom sugar, see Trehalose Mustard seed emulsin, 600 Mutarotase, 50
Mutarotation, 29, 49-57
penta-O-acetyl -aldehydo-hexoses, 145 activation energies, 52
coefficients, 52 complex, 51 effect of pH, 55 enzymic catalysis, 50 equations, 50, 52
generalized acid-base catalysis, 55 D-glucose, 53
N-glycosylamines, 420 kinetics, 55-7
lactones, 306 oligosaccharides, 488
oximes, 463
phenylhydrazones, 454 phenylosazones, 459 L-ribose, 53 D-talose, 53 Mycarose, 78 Mycodextrans, 706 Mycose, see Trehalose My rosin, 555
Myrtillin, 88
Mytilitol, see sq//Zo-Inositol, methyl M y Ulis edilis, 278
N Nataloin, 83
Naphthoresorcinol test, D-gluconic acid, 2-keto, 327 uronic acids, 318
Naringin, 100 Nebularine, 425
Neisseria meningitidis, phosphorylase, 527
Neisseria perflava, amylosucrase, 705 D-Neogalactide, see D-Galactitol,
l,5:3,6-dianhydro Neokestose, 532
Neolactose, see D-Altrose, 4-Ο-β-Ώ-galactosyl
Neomannide, see D-Mannitol, 1,5:3,6-dianhydro
Neomycin, 297
Neosorbide, see D-Glucitol, 1,5:3,6-dianhydro
Nervone, 560 Neuberg ester, 181
Neuraminic acid, see also Sialic acid, 475
gangliosides, 560 Neurospora crassa, 471
pectinase, 672
Niacin, see Nicotinic acid Nickel, see Raney nickel Nicotinamide, 418 ,437,745
JV- (tetra-O-acetyl-D-glucosyl), 1,2-dihydro, 418
1,6-dihydro, 418
Nicotinic acid, requirement in fructose metabolism, 787
Nigeran, 706 Nitrates, 168
O-acylglycosyl nitrates, 169
decomposition mechanism, 170 instability, 169
polysaccharides, 693 denitration, 693 preparation, 169
primary, replacement of halogen or sulfonate, 169
reductive denitration, 170 reductive hydrolysis, 165 saponification, 170
Nitric acid oxidation, see also Nitrogen dioxide,
methylated saccharides, 212-214, 353 polyols, 246, 290
saccharides, 313, 353 products, 354
vanadium pentoxide catalysis, 353 C-Nitroalcohols, see also Nitromethane
synthesis, 131
2-deoxyaldose preparation, 131 Nitroethanol synthesis, see also
Nitro-methane synthesis, 111 preparation of,
D-grfo/co-heptulose, 111 D-manno-heptulose, 101, 111 Nitrogen dioxide oxidation, 354
mechanism, 355 polysaccharides, 699 specificity, 354
Nitromethane synthesis (Sowden-Fischer), 109
for lengthening carbon chain, 109 preparation of,
O-erythro-L-manno-octose, 110 L-glucose, 110
L-gulose, 110
heptoses from D-mannose, 110 L-mannose, 110
C-nitrodeoxyinositols, 110*
separation of epimers, 109
Nitrophenols, reducing sugar tests, 608 Nitrous acid,
anhydro derivatives, formation, 378 deamination, 378
mechanism, 380 Nomenclature,
D- and L, 21
selection of reference group, 23 higher carbon sugars, 44-9 oligosaccharides, 480 Nonitols, 257
Notatin, 366
Nucleic acids, see also Ribonucleic acids, Deoxyribonucleic acids, 84,441-6 genetic implications, 445
histochemistry, 635 hydrolysis, 441
catalysts, 425 isolation, 441 occurrence, 441 structure, 442 Nucleoproteins, 635 Nucleosides, 424
diphosphoric acids, 435, 437 triphosphoric acids, 435, 437 phosphorylated, see Nucleotides preparation, 425
separation, 426 structure, 426
anomeric configuration, 428 point of attachment, sugar to base,
428
sugar-ring size, 427 synthesis, 429
enzymic, 426 Nucleotides, 430, 746
acid-labile phosphate, 432 acid-stable phosphate, 432
diphosphopyridine (DPN), 437, 745 triphosphopyridine (TPN), 438, 745 related substances,
B-group vitamins, 437 coenzymes, 437 structure, 431 preparation, 430 separation, 430, 431 Nylon, 666