Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡

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 a...

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Main Authors:	Vavříková, Eva, Gavezzotti, Paolo, Purchartová, Kateřina, Fuksová, Kateřina, Biedermann, David, Kuzma, Marek, Riva, Sergio, Křen, Vladimír
Format:	Online
Language:	English
Published:	MDPI 2015
Online Access:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4490424/

id	pubmed-4490424
recordtype	oai_dc
spelling	pubmed-44904242015-07-07 Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡ Vavříková, Eva Gavezzotti, Paolo Purchartová, Kateřina Fuksová, Kateřina Biedermann, David Kuzma, Marek Riva, Sergio Křen, Vladimír Article 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. MDPI 2015-05-26 /pmc/articles/PMC4490424/ /pubmed/26016503 http://dx.doi.org/10.3390/ijms160611983 Text en © 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
repository_type	Open Access Journal
institution_category	Foreign Institution
institution	US National Center for Biotechnology Information
building	NCBI PubMed
collection	Online Access
language	English
format	Online
author	Vavříková, Eva Gavezzotti, Paolo Purchartová, Kateřina Fuksová, Kateřina Biedermann, David Kuzma, Marek Riva, Sergio Křen, Vladimír
spellingShingle	Vavříková, Eva Gavezzotti, Paolo Purchartová, Kateřina Fuksová, Kateřina Biedermann, David Kuzma, Marek Riva, Sergio Křen, Vladimír Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡
author_facet	Vavříková, Eva Gavezzotti, Paolo Purchartová, Kateřina Fuksová, Kateřina Biedermann, David Kuzma, Marek Riva, Sergio Křen, Vladimír
author_sort	Vavříková, Eva
title	Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡
title_short	Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡
title_full	Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡
title_fullStr	Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡
title_full_unstemmed	Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡
title_sort	regioselective alcoholysis of silychristin acetates catalyzed by lipases ‡
description	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.
publisher	MDPI
publishDate	2015
url	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4490424/
_version_	1613243565882736640

Regioselective Alcoholysis of Silychristin Acetates Catalyzed by Lipases ‡

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