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cis-trans Isomerization of silybins A and B.
Novotná, Michaela; Gazák, Radek; Biedermann, David; Di Meo, Florent; Marhol, Petr; Kuzma, Marek; Bednárová, Lucie; Fuksová, Katerina; Trouillas, Patrick; Kren, Vladimír.
Afiliação
  • Novotná M; Institute of Microbiology, v.v.i. AS CR, Vídenská 1083, Prague 4, CZ-14220, Czech Republic.
  • Gazák R; Institute of Microbiology, v.v.i. AS CR, Vídenská 1083, Prague 4, CZ-14220, Czech Republic.
  • Biedermann D; Department of Biochemistry, Faculty of Science, Charles University in Prague, Hlavova 8, CZ-12840 Prague 2, Czech Republic.
  • Di Meo F; Institute of Microbiology, v.v.i. AS CR, Vídenská 1083, Prague 4, CZ-14220, Czech Republic.
  • Marhol P; Inserm UMR-S850, Faculté de Pharmacie, Université de Limoges, 2 Rue du Docteur Marcland, F-87025 Limoges, France.
  • Kuzma M; Present address: Department of Physics, Chemistry and Biology (IFM), Linköping University, SE-58183, Linköping, Sweden.
  • Bednárová L; Institute of Microbiology, v.v.i. AS CR, Vídenská 1083, Prague 4, CZ-14220, Czech Republic.
  • Fuksová K; Institute of Microbiology, v.v.i. AS CR, Vídenská 1083, Prague 4, CZ-14220, Czech Republic.
  • Trouillas P; Institute of Organic Chemistry and Biochemistry, v.v.i. AS CR, Flemingovo námestí 2, Prague 6, CZ-16610, Czech Republic.
  • Kren V; Institute of Microbiology, v.v.i. AS CR, Vídenská 1083, Prague 4, CZ-14220, Czech Republic.
Beilstein J Org Chem ; 10: 1047-1063, 2014.
Article em En | MEDLINE | ID: mdl-24991256
ABSTRACT
Methods were developed and optimized for the preparation of the 2,3-cis- and the 10,11-cis-isomers of silybin by the Lewis acid catalyzed (BF3∙OEt2) isomerization of silybins A (1a) and B (1b) (trans-isomers). The absolute configuration of all optically pure compounds was determined by using NMR and comparing their electronic circular dichroism data with model compounds of known absolute configurations. Mechanisms for cis-trans-isomerization of silybin are proposed and supported by quantum mechanical calculations.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2014 Tipo de documento: Article
Texto completo
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2014 Tipo de documento: Article