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Regioselective alcoholysis of silychristin acetates catalyzed by lipases.

Vavříková E, Gavezzotti P, Purchartová K, Fuksová K, Biedermann D, Kuzma M, Riva S, Křen V - Int J Mol Sci (2015)

Bottom Line: 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 Article: PubMed Central - PubMed

Affiliation: Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 142 20 Prague, Czech Republic. vavrikova@biomed.cas.cz.

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.

No MeSH data available.


Enzymatic acetylation of silychristin (1) and alcoholysis of 22-O-acetyl-silychristin (2). Lipase PS (Pseudomonas cepacia), Sigma; MTBE, methyl tert-butyl ether.
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ijms-16-11983-f006: Enzymatic acetylation of silychristin (1) and alcoholysis of 22-O-acetyl-silychristin (2). Lipase PS (Pseudomonas cepacia), Sigma; MTBE, methyl tert-butyl ether.


Regioselective alcoholysis of silychristin acetates catalyzed by lipases.

Vavříková E, Gavezzotti P, Purchartová K, Fuksová K, Biedermann D, Kuzma M, Riva S, Křen V - Int J Mol Sci (2015)

Enzymatic acetylation of silychristin (1) and alcoholysis of 22-O-acetyl-silychristin (2). Lipase PS (Pseudomonas cepacia), Sigma; MTBE, methyl tert-butyl ether.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4490424&req=5

ijms-16-11983-f006: Enzymatic acetylation of silychristin (1) and alcoholysis of 22-O-acetyl-silychristin (2). Lipase PS (Pseudomonas cepacia), Sigma; MTBE, methyl tert-butyl ether.
Bottom Line: 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 Article: PubMed Central - PubMed

Affiliation: Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ 142 20 Prague, Czech Republic. vavrikova@biomed.cas.cz.

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.

No MeSH data available.