1. Enzymatic kinetic resolution of silybin diastereoisomers.
- Author
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Monti D, Gazák R, Marhol P, Biedermann D, Purchartová K, Fedrigo M, Riva S, and Kren V
- Subjects
- Bacteria enzymology, Combinatorial Chemistry Techniques, Enzymes, Immobilized, Fungal Proteins, Kinetics, Silybum marianum chemistry, Molecular Structure, Silybin, Silymarin chemical synthesis, Silymarin isolation & purification, Stereoisomerism, Hydrolases metabolism, Lipase metabolism, Silymarin chemistry
- 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.
- Published
- 2010
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