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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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https://hal-pasteur.archives-ouvertes.fr/pasteur-00167058
Contributor : Sylvie Bay <>
Submitted on : Tuesday, August 14, 2007 - 2:24:49 PM
Last modification on : Monday, January 13, 2020 - 5:08:05 PM

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

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

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