In situ proton NMR study of acetyl and formyl group migration in mono-O-acyl D-glucose
✍ Scribed by Lothar Brecker; Marek Mahut; Alexandra Schwarz; Bernd Nidetzky
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 152 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0749-1581
- DOI
- 10.1002/mrc.2395
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✦ Synopsis
Abstract
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.