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β‐glycosidases: Tools for chiral discrimination
Author(s) -
Zarevúcka Marie,
Vacek Miroslav,
Kuldová Jelena,
Šaman David,
Wimmer Zdeněk,
Weignerová Lenka,
Křen Vladimír
Publication year - 1999
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(1999)11:5/6<451::aid-chir16>3.0.co;2-d
Subject(s) - chemistry , stereoselectivity , diastereomer , bacillus circulans , glycoside , glycosidic bond , alkyl , galactosidases , kluyveromyces lactis , stereochemistry , organic chemistry , hydrolysis , cyclohexanol , chirality (physics) , enzyme , biochemistry , escherichia coli , beta galactosidase , catalysis , yeast , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , gene , saccharomyces cerevisiae
The almond β‐glucosidase, and the β‐galactosidases from Escherichia coli, Kluyveromyces lactis, and Bacillus circulans were used to catalyze the stereoselective hydrolysis of diastereoisomeric mixtures of alkyl‐β‐D‐glucopyranosides and alkyl‐β‐D‐galactopyranosides which were derived from the cis ‐ and trans ‐isomers of 2‐(4‐alkoxybenzyl)‐1‐cyclohexanols by the Koenigs‐Knorr synthesis. Stereoselective preference of the enzymes towards the respective diastereoisomers of the glycosides were studied (both chiral alcohols and alkyl‐ O ‐glycosides were prepared). Higher stereoselectivity was achieved for the glycosides derived from trans ‐2‐(4‐alkoxybenzyl)‐1‐cyclohexanols. The practical significance of this research is in the biological screening of selected alkyl‐ O ‐glycosides (glycosidic juvenogens, i.e., biochemically activated hormonogen complexes), using the β‐glycosidases studied, as modern systemic and environmentally safe pesticides. Chirality 11:451–458, 1999. © 1999 Wiley‐Liss, Inc.