A chemoenzymatic synthesis of the O-glycosides

✍ Scribed by Marie Zarevúcka; Miroslav Vacek; Zdeněk Wimmer; Kateřina Demnerová; Martina Macková

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 128 KB
• Volume: 10
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1998)10:7<676::aid-chir13>3.0.co;2-x

✦ Synopsis

Almond ␤-glucosidase was used to catalyze the synthesis of alkyl ␤-Dglucopyranosides 1b-3b starting from either D-glucose (4) or phenyl-␤-Dglucopyranoside (5) and the racemic alcohols 1a-3a. The enzymic reactions were provided in different acetonitrile/water mixtures [9:1 (v/v) for the reverse hydrolysis, and 1:9 (v/v) for the transglycosylation]. Both enzymic reactions, that is, the reverse hydrolysis and the transglucosylation, are enantioselective processes. The enantiomeric purity of products 1b-2b of the enzymic reactions varied between 75 and 86% ee, the values of which were based on the analysis of the aglyconic parts (1c-2c) of the alkyl ␤-D-glucopyranoside molecules (1b-2b).