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Cis-trans isomerization of silybins A and B
1Institute of Microbiology, V.V.I. AS CR, Vídeňská 1083, Prague 4, CZ-14220, Czech Republic.
1Institute of Microbiology, V.V.I. AS CR, Vídeňská 1083, Prague 4, CZ-14220, Czech Republic; Department of Biochemistry, Faculty of Science, Charles University of in Prague, Hlavova 8, CZ-12840 Prague 2, Czech Republic.
1Institute of Microbiology, V.V.I. AS CR, Vídeňská 1083, Prague 4, CZ-14220, Czech Republic.
Inserm UMR-S850, Faculté de Pharmacie, Université de Limoges, 2 Rue du Docteur Marcland, F-87025 Limoges, France.
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2014 (English)In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 10, 1047-1063 p.Article in journal (Refereed) Published
Abstract [en]

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 (BF 3-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. © 2014 Novotná et al; licensee Beilstein-Institut.

Place, publisher, year, edition, pages
Beilstein-Institut , 2014. Vol. 10, 1047-1063 p.
Keyword [en]
10, 11-cis-silybin; 2, 3-cis-silybin; Isomerization; Silibinin; Silybin; Silymarin
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:liu:diva-116387DOI: 10.3762/bjoc.10.105PubMedID: 24991256Scopus ID: 2-s2.0-84901370892OAI: oai:DiVA.org:liu-116387DiVA: diva2:798664
Note

Funding Agencies|P207/10/0288, GACR, Czech Science Foundation

Available from: 2015-03-27 Created: 2015-03-26 Last updated: 2017-12-04

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