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Two-step enzymatic modification of solid-supported bergenin in aqueous and organic media
- Issue Date
- Feb-2010
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Citation
- TETRAHEDRON LETTERS, v.51, no.8, pp 1220 - 1225
- Pages
- 6
- Journal Title
- TETRAHEDRON LETTERS
- Volume
- 51
- Number
- 8
- Start Page
- 1220
- End Page
- 1225
- ISSN
- 0040-4039
- Abstract
- The natural flavonoid bergenin was directly immobilized onto carboxylic acid-functionalized controlled pore glass (carboxy-CPG) at 95% yield. Immobilized bergenin was brominated via chloroperoxidase in aqueous solution and then transesterified with vinyl butyrate in diisopropyl ether by subtilisin carslberg (SC) extracted into the organic solvent via ion-pairing. Enzymatic cleavage of 7-bromo-4-butyrylbergenin from carboxy-CPG (9.6% final yield) was accomplished using lipase B (LipB) in an aqueous/organic mixture (90/10 v/v of water/acetonitrile), demonstrating the feasibility of solid-phase biocatalysis of a natural product in aqueous and non-aqueous media. (C) 2009 Elsevier Ltd. All rights reserved.
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