Enzymatic kinetic resolution of sylibin diastereoisomers

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.