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Highly Regioselective Hydroxylation of Polydatin, a Resveratrol Glucoside, for One-Step Synthesis of Astringin, a Piceatannol Glucoside, by P450 BM3

Highly Regioselective Hydroxylation of Polydatin, a Resveratrol Glucoside, for One-Step Synthesis of Astringin, a Piceatannol Glucoside, by P450 BM3

Thien-Kim Le, Hyun-Hee Jang, Ha Thi Huong Nguyen, Tiep Thi My Doan, Ga-Young Lee, Ki Deok Park, Taeho Ahn, Young Hee Joung, Hyung-Sik Kang, Chul-Ho Yun

Enzyme Microb Technol. 2017 Feb;97:34-42.

PMID: 28010771

Abstract:

Enzymatic conversion of natural glycosides to their corresponding hydroxylated products using cytochromes P450 has significant advantages over synthetic chemistry and even enzyme-catalyzed glycosylation of chemicals. At present, the basic strategy for making glycosides of stilbenoid compounds is to use the glycosylation activity of enzymes, such as glycosyltransferases. Here, an efficient synthesis of a valuable (E)-astringin, a piceatannol glucoside, was developed using CYP102A1 via the highly regioselective C-3' hydroxylation of polydatin, a resveratrol glucoside. (E)-astringin is a high added value compound found in plants and wine. Benzylic hydroxylation of polydatin provides an attractive route to (E)-astringin, a catechol product. Thus far, chemical and enzymatic methods of producing (E)-astringin have not been developed. In the present study, a set of CYP102A1 mutants from Bacillus megaterium was found to catalyze regioselective hydroxylation of polydatin at the C-3' position to generate an (E)-astringin, a piceatannol glucoside.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP29884499	Astringin		29884-49-9	Price

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