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A chemoenzymatic synthesis of the O ‐glycosides
Author(s) -
Zarevúcka Marie,
Vacek Miroslav,
Wimmer Zdeněk,
Demnerová Kateřina,
Macková Martina
Publication year - 1998
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1998)10:7<676::aid-chir13>3.0.co;2-x
Subject(s) - chemistry , hydrolysis , enantioselective synthesis , chirality (physics) , enantiomer , acetonitrile , glycoside , alkyl , stereochemistry , organic chemistry , enantiomeric excess , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Almond β‐glucosidase was used to catalyze the synthesis of alkyl β‐d‐glucopyranosides 1b–3b starting from either d‐glucose ( 4 ) or phenyl‐β‐d‐glucopyranoside ( 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 β‐d‐glucopyranoside molecules ( 1b–2b ). Chirality 10:676–681, 1998. © 1998 Wiley‐Liss, Inc.