MICROBIAL XYLANOLYTIC CARBOHYDRATE ESTERASES
4. USE OF ACETYL XYLAN ESTERASES AND FERULIC ACID ESTERASES AS BIOSYNTHETIC TOOLS
an inactive mutant of AnFaeA (S133A) in complex with O-{5-O-[(E)-feruloyl]--L-arabinofuranosyl}-(1→3)-O--D-xylopyranosyl-(1→4)-D-xylopyranose (FAX2) and observed that the ferulic acid moiety of the substrate was visible in the electron density map showing interactions through its OH and OCH3 groups with the hydroxyl groups of Tyr80. However, the remaining groups of the substrate (i.e.the arabinose and the two xylose units) were not visible. Accordingly, in the structure of the XynZ FAE in complex with FAX2determined by Schubotet al.(2001), the ferulic moiety was clearly visible in the active site while the carbohydrate parts of the substrate were not, suggesting that tight binding of the carbohydrate is not required for catalysis. These results are in agreement with the synthetic ability of StFaeC in non-conventional media where the esterase seems to be able to esterify a broad spectrum of sugars showing specificity only to the ferulic moiety (Vafiadi et al., 2005). In contrast to FAEs, determination of the crystal structure of a family 10 xylanase fromThermoascus aurantiacuscomplexed with xylobiose containing an arabinofuranosyl-ferulate side-chain, revealed that the distal glycone subsite of the enzyme makes extensive direct and indirect interactions with the arabinose side-chain, while the ferulate moiety is solvent-exposed (Vardakouet al., 2005).
4. USE OF ACETYL XYLAN ESTERASES AND FERULIC ACID
Transesterification of phenolic acids was catalysed by using a type A FAE fromF. oxysporum(FoFaeA) trapped in an-hexane/1-propanol/water surfactantless microemulsion (Topakaset al., 2003a). Greater synthetic activity was observed in ternary water-organic mixtures having a lower water content. The synthetic activity of esterases follows a pattern similar to their hydrolytic activity against various methyl esters of cinnamic acids. FoFaeA shows a preference for the hydrolysis of methoxylated substrates (Topakaset al., 2005b) while conversion to butyl esters was greater with ferulic and sinapinic acids. Type B esterases from F. oxysporum (FoFaeB) (Topakaset al., 2003b) andS. thermophile(StFaeB) showed preference for the hydrolysis of hydroxylated substrates (Topakas et al., 2005b) and the conversion to butyl esters was enhanced withp-coumaric and caffeic acids (Topakas et al., 2003b, 2004). The type-C FAE StFaeC fromS. thermophile demonstrated maximum hydrolytic activity against methyl ferulate (Topakas et al., 2005b).
Optimal yields were achieved producing butyl esters with ferulic acid (Topakas et al., 2005a). Furthermore, it was reported that the same enzyme catalysed the transfer of the feruloyl group to L-arabinose (Fig. 2) in a ternary water-organic mixture consisting ofn-hexane,t-butanol and water system, achieving a conversion of about 40% of L-arabinose to a feruloylated derivative (Topakaset al., 2005a).
This work was the first example of sugar esterification with unsaturated arylaliphatic acids, like methoxylated or hydroxylated derivatives of cinnamic acids (such as ferulic acid). Lipases are not able to catalyse such a reaction due to electronic and/or steric effects (Ottoet al., 2000).
Phenolic acid sugar esters have demonstrable antitumoural activity and the potential to be used to formulate antimicrobial, antiviral and/or anti-inflammatory agents. As esters based on unsaturated arylaliphatic acids such as cinnamic acid and its derivatives are known to display anticancer activity, specific FAEs could be employed in the tailored synthesis of such pharmaceuticals.
The potential use of FAEs for the synthesis of feruloylated oligomers or polymers using feruloyl esterases opens the door for the design of modified biopolymers with new properties and bioactivities.
Figure 2.Transesterification of methyl ferulate with L-arabinose by StFaeC
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