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Int. J. Mol. Sci. 2015, 16(6), 11983-11995; doi:10.3390/ijms160611983

Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases

1
Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 142 20 Prague, Czech Republic
2
Istituto di Chimica del Riconoscimento Molecolare, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, I 20131 Milano, Italy
This paper is dedicated to the memory of the late Prof. Bruno Danieli, Professor of Organic Chemistry, Università degli Studi di Milano, 20122 Milano, Italy.
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Ritva Tikkanen
Received: 27 April 2015 / Accepted: 19 May 2015 / Published: 26 May 2015
(This article belongs to the Special Issue Molecular Biocatalysis)
View Full-Text   |   Download PDF [1471 KB, uploaded 26 May 2015]   |  

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. View Full-Text
Keywords: silychristin; silymarin; lipase; acetylation; alcoholysis silychristin; silymarin; lipase; acetylation; alcoholysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Vavříková, E.; Gavezzotti, P.; Purchartová, K.; Fuksová, K.; Biedermann, D.; Kuzma, M.; Riva, S.; Křen, V. Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases. Int. J. Mol. Sci. 2015, 16, 11983-11995.

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