Large-scale separation of silybin diastereoisomers using lipases |
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Institution: | 1. Renewable Products Technology Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA;2. Bacterial Foodborne Pathogens and Mycology, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA;3. Functional Foods Research, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA;4. Plant Polymer Research, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 N. University Street, Peoria, IL 61604, USA |
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Abstract: | The flavonolignan silybin (1), isolated from the seeds of milk thistle (Silybum marianum), occurs in nature as an equimolar mixture of two diastereoisomers, silybin A and silybin B, that exhibit different biological activities. The preparative production of optically pure silybin A and B in a diastereoisomeric purity greater than 95% was accomplished using immobilized Candida antarctica lipase B (Novozym 435) in a combination of two reactions: regioselective acetylation of a natural silybin mixture (1) and subsequent stereoselective alcoholysis of the resulting 23-O-acetylsilybin (2). Several grams of the optically pure substances can be produced within one week using this new, robust and scalable process, which is selective, mild and high-yielding. |
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