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In situ proton NMR study of acetyl and formyl group migration in mono‐ O ‐acyl D ‐glucose
Author(s) -
Brecker Lothar,
Mahut Marek,
Schwarz Alexandra,
Nidetzky Bernd
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2395
Subject(s) - chemistry , mutarotation , formate , hydrolysis , stereochemistry , in situ , leuconostoc mesenteroides , nuclear magnetic resonance spectroscopy , medicinal chemistry , catalysis , organic chemistry , lactic acid , biology , bacteria , genetics
Acetyl and formyl group migration, mutarotation, and hydrolysis of mono‐ O ‐acylated glucose are studied by in situ 1D and 2D 1 H NMR spectroscopy. α‐ D ‐Glucosyl‐1‐acetate and α‐ D ‐glucosyl‐1‐formate serve as sole starting materials. They are generated in situ by configuration retaining glucosyltransfer from α‐ D ‐glucosyl‐1‐phosphate to formate and acetate, which is catalyzed by the Glu‐237 → Gln mutant of Leuconostoc mesenteroides sucrose phosphorylase. Temporary accumulated regio‐isomeric mono‐ O ‐acyl D ‐glucoses are identified, characterized, and quantified directly from the reaction mixture. Time courses of the transformations give insight into pH dependence of acyl group migration and mutarotation as well as into the stability of various regioisomers. Copyright © 2009 John Wiley & Sons, Ltd.