Regioselective alcoholysis of silychristin acetates catalyzed by lipases

0444945 - MBÚ 2016 RIV CH eng J - Článek v odborném periodiku
Vavříková, Eva - Gavezzotti, P. - Purchartová, Kateřina - Fuksová, Kateřina - Biedermann, David - Kuzma, Marek - Riva, S. - Křen, Vladimír
Regioselective alcoholysis of silychristin acetates catalyzed by lipases.
International Journal of Molecular Sciences. Roč. 16, č. 6 (2015), s. 11983-11995. E-ISSN 1422-0067
Grant CEP: GA ČR(CZ) GA15-03037S; GA MŠMT(CZ) LD14096; GA MŠMT LH13097
Institucionální podpora: RVO:61388971
Klíčová slova: acetylation * alcoholysis * lipase
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 3.257, rok: 2015

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.
Trvalý link: http://hdl.handle.net/11104/0247384