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Synthesis of alpha and beta-glycopyranosyl-serine derivatives by enzymic transglycosylation.

Abstract : The transglycosylation from raffinose and lactose to Aloc-Ser-OMe is catalyzed respectively by alpha and beta galactosidases. Transglycosylation from cellobiose has been achieved with beta-glucosidase. The simplicity of the enzymatic synthesis, the stereospecificity of the condensations in one-pot reactions and the ease of purification give the method value for large scale preparation of beta-linked derivatives. The protective groups of the serine residue can be cleaved under mild conditions: the ester group has been removed quantitatively by papain catalyzed hydrolysis and the Aloc group by a Pd (0) hydrostannolytic cleavage.
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Contributor : Sylvie Bay Connect in order to contact the contributor
Submitted on : Tuesday, August 14, 2007 - 2:24:49 PM
Last modification on : Thursday, April 7, 2022 - 10:10:19 AM


  • HAL Id : pasteur-00167058, version 1
  • PUBMED : 1668139



D. Cantacuzene, S. Attal, S. Bay. Synthesis of alpha and beta-glycopyranosyl-serine derivatives by enzymic transglycosylation.. Biomedica Biochimica Acta, 1991, 50 (10-11), pp.S231-6. ⟨pasteur-00167058⟩



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