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Enzymatic kinetic resolution of sylibin diastereoisomers (Articolo in rivista)

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Enzymatic kinetic resolution of sylibin diastereoisomers (Articolo in rivista) (literal)

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Monti D., Gazak R., Marhol P., Biedermann D., Purchartova K., Fedrigo M., Riva S., Kren V. (2010)
Enzymatic kinetic resolution of sylibin diastereoisomers
in Journal of natural products (Print)
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Monti D., Gazak R., Marhol P., Biedermann D., Purchartova K., Fedrigo M., Riva S., Kren V. (literal)

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Institute of Microbiology, Centre of Biocatalysis and Biotransformation, Academy of Sciences of the Czech Republic, V?denska 1083, CZ-142 20 Prague, Czech Republic, and Istituto di Chimica del Riconoscimento Molecolare, CNR, Via Mario Bianco 9, I-20131 Milano, Italy (literal)

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Abstract

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. (literal)

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