Synthesis of alpha and beta-glycopyranosyl-serine derivatives by enzymic transglycosylation.
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.
Cantacuzene
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Département de Biochimie et Génétique Moléculaire, Institut Pasteur, Paris, France.
Attal
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Bay
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D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D012694:Serine / Q000737:chemistry; D000519:alpha-Galactosidase / Q000737:chemistry; D001616:beta-Galactosidase / Q000737:chemistry; D001617:beta-Glucosidase / Q000737:chemistry
D006020:Glycopeptides; D012694:Serine; D001617:beta-Glucosidase; D000519:alpha-Galactosidase; D001616:beta-Galactosidase