title: Chiral resolution through stereoselective transglycosylation by sucrose phosphorylase: application to the synthesis of a new biomimetic compatible solute, (R)-2-O-α-D-glucopyranosyl glyceric acid amide.
abstract: Sucrose phosphorylase catalysed glycosylation of glyceric acid amide with complete regio- and diastereo-selectivity is studied. (R)-2-O-α-D-Glucopyranosyl glyceric acid amide was obtained in high yield from single-step transformation of racemic glyceric acid amide and sucrose. Non-productive binding of (S)-glyceric acid amide appeared to underlie strict enantiodiscrimination by the enzyme, thus supporting chiral resolutions based on stereoselective transglycosylation.
authors.affiliation: Institute of Biotechnology and Biochemical Engineering, Graz University of Technology, Petersgasse 12/1, A-8010 Graz, Austria. bernd.nidetzky@tugraz.at.
authors.forename: Patricia
authors.initials: P
authors.lastname: Wildberger
authors.forename: Lothar
authors.initials: L
authors.lastname: Brecker
authors.forename: Bernd
authors.initials: B
authors.lastname: Nidetzky
mesh_terms: D055162:Biocatalysis; D001672:Biocompatible Materials / Q000737:chemistry / Q000378:metabolism*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D005964:Glucosyltransferases / Q000737:chemistry / Q000378:metabolism*; D005988:Glyceric Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006031:Glycosylation; D011485:Protein Binding; D013237:Stereoisomerism; D013395:Sucrose / Q000378:metabolism
chemical_list: D001672:Biocompatible Materials; D005960:Glucosides; D005988:Glyceric Acids; D013395:Sucrose; C042971:glyceric acid; D005964:Glucosyltransferases; C025901:sucrose phosphorylase