Issue 4, 2014
From the journal:

Chemical Communications

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†

Patricia Wildberger,a   Lothar Breckerb  and  Bernd Nidetzky*a  

* Corresponding authors

a Institute of Biotechnology and Biochemical Engineering, Graz University of Technology, Petersgasse 12/1, A-8010 Graz, Austria
E-mail: bernd.nidetzky@tugraz.at

b Institute of Organic Chemistry, University of Vienna, Währingerstraße 38, A-1090 Vienna, Austria

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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/C3CC47249C
Article type
Communication
Submitted
22 Sep 2013
Accepted
29 Oct 2013
First published
30 Oct 2013
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2014,50, 436-438

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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

P. Wildberger, L. Brecker and B. Nidetzky, Chem. Commun., 2014, 50, 436 DOI: 10.1039/C3CC47249C

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