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Enzymatic Kinetic Resolution of Silybin Diastereoisomers ( perpendicular).

Daniela Monti, Radek Gažák, Petr Marhol, David Biedermann, Kateřina Purchartová, Mirko Fedrigo, Sergio Riva, and Vladimír Křen

J Nat Prod 73(4):613-9 (2010) PMID 20297826

In nature, the flavonolignan silybin (1) occurs as a mixture of two diastereomers, silybin A and silybin B, which in a number of biological assays exhibit different activities. A library of hydrolases (lipases, esterases, and proteases) was tested for separating the silybin A and B diastereomers by selective transesterification or by stereoselective alcoholysis of 23-O-acetylsilybin (2). Novozym 435 proved to be the most suitable enzyme for the preparative production of both optically pure silybins A and B by enzymatic discrimination. Gram amounts of the optically pure substances can be produced within one week, and the new method is robust and readily scalable to tens of grams.

DOI: 10.1021/np900758d
Version: za2963e q8za7 q8zb9 q8zc8 q8zde q8ze4 q8zfa q8zg1
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