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Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases

Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases

Eva Vavříková, Paolo Gavezzotti, Kateřina Purchartová, Kateřina Fuksová, David Biedermann, Marek Kuzma, Sergio Riva, Vladimír Křen

Int J Mol Sci. 2015 May 26;16(6):11983-95.

PMID: 26016503

Abstract:

A panel of lipases was screened for the selective acetylation and alcoholysis of silychristin and silychristin peracetate, respectively. Acetylation at primary alcoholic group (C-22) of silychristin was accomplished by lipase PS (Pseudomonas cepacia) immobilized on diatomite using vinyl acetate as an acetyl donor, whereas selective deacetylation of 22-O-acetyl silychristin was accomplished by Novozym 435 in methyl tert-butyl ether/ n-butanol. Both of these reactions occurred without diastereomeric discrimination of silychristin A and B. Both of these enzymes were found to be capable to regioselective deacetylation of hexaacetyl silychristin to afford penta-, tetra- and tri-acetyl derivatives, which could be obtained as pure synthons for further selective modifications of the parent molecule.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP33889699-A	Silychristin		33889-69-9	Price

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