Regioselective acylation of several polyhydroxylated natural compounds by Candida antarctica lipase B |
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Authors: | Rong-Wei Teng Thi-Kim-Anh Bui David McManus David Armstrong Shaio-Lim Mau |
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Institution: | 1. CRC for Bioproducts, School of Botany, The University of Melbourne, Victoria, 3010, Australiatengrongwei@hotmail.com;3. Ho Chi Minh City University of Technology, Ho Chi Ming City, Vietnam;4. CRC for Bioproducts, Tridan–Albright &5. Wilson (Aust) Ltd Partnership, Victoria, 3013, Australia;6. CRC for Bioproducts, School of Botany, The University of Melbourne, Victoria, 3010, Australia |
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Abstract: | Regioselective acylation of four polyhydroxylated natural compounds, deacetyl asperulosidic acid (1), asperulosidic acid (2), puerarin (3) and resveratrol (4) by Candida antarctica Lipase B in the presence of various acyl donors (vinyl acetate, vinyl decanoate or vinyl cinnamoate) was studied. Compounds 1, 2 and 4 were regioselectively acetylated with vinyl acetate to afford products, 3′-O-acetyl-10-O-deacetylasperulosidic acid (1a), 3′,6′-O-diacetyl-10-O-deacetylasperulosidic acid (1b), 3′-O-acetylasperulosidic acid (2a), 3′,6′-O-diacetylasperulosidic acid (2b), 4′-O-acetylresveratrol (4a), respectively, with yields of 22 to 50%, while reactions with vinyl decanoate and vinyl cinnamoate were slow with lower yields. Compound 3 was readily acylated with all three acyl donors and quantitatively converted to products 6″-O-acetylpuerarin (3a), 6″-O-decanoylpuerarin (3b), 6″-O-cinnamoylpuerarin (3c), respectively. The structures of these acylated products were determined by spectroscopic methods (MS and NMR). |
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Keywords: | Acylation asperulosidic acid Candida antarctica Lipase B deacetyl asperulosidic acid puerarin resveratrol |
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