Sucrose phosphorylase catalysed glycosylation of glyceric acid amide with complete regio-and diastereo-selectivity is studied. (R)-2-O-a-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. † Electronic supplementary

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... nformation (ESI) available: Experimental procedures used; NMR spectra of 3; the CD spectrum of residual 2 isolated from the reaction mixture; docking poses of R and S-forms of 1,2-diol acceptors glucosylated by sucrose phosphorylase; time course of synthesis of 3; active-site superimposition for sucrose phosphorylases from B. adolescentis and L. mesenteroides; table summarising reaction conditions and product yields. See