title: Highly regioselective hydroxylation of polydatin, a resveratrol glucoside, for one-step synthesis of astringin, a piceatannol glucoside, by P450 BM3.
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.
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea.
authors.forename: Thien-Kim
authors.initials: TK
authors.lastname: Le
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea.
authors.forename: Hyun-Hee
authors.initials: HH
authors.lastname: Jang
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea.
authors.forename: Ha Thi Huong
authors.initials: HT
authors.lastname: Nguyen
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea.
authors.forename: Tiep Thi My
authors.initials: TT
authors.lastname: Doan
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea.
authors.forename: Ga-Young
authors.initials: GY
authors.lastname: Lee
authors.affiliation: Gwangju Center, Korea Basic Science Institute, Gwangju 61186, Republic of Korea.
authors.forename: Ki Deok
authors.initials: KD
authors.lastname: Park
authors.affiliation: College of Veterinary Medicine, Chonnam National University, Gwangju 61186, Republic of Korea.
authors.forename: Taeho
authors.initials: T
authors.lastname: Ahn
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea.
authors.forename: Young Hee
authors.initials: YH
authors.lastname: Joung
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea.
authors.forename: Hyung-Sik
authors.initials: HS
authors.lastname: Kang
authors.affiliation: School of Biological Sciences and Technology, Chonnam National University, 77 Yongbongro, Gwangju 61186, Republic of Korea. Electronic address: chyun@jnu.ac.kr.
authors.forename: Chul-Ho
authors.initials: CH
authors.lastname: Yun
mesh_terms: D019943:Amino Acid Substitution; D001410:Bacillus megaterium / Q000201:enzymology / Q000235:genetics; D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D055162:Biocatalysis; D001709:Biotechnology; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism*; D005960:Glucosides / Q000096:biosynthesis* / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D007700:Kinetics; D016297:Mutagenesis, Site-Directed; D009251:NADPH-Ferrihemoprotein Reductase / Q000235:genetics / Q000378:metabolism*; D015202:Protein Engineering; D013267:Stilbenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001426:Bacterial Proteins; D005960:Glucosides; D013267:Stilbenes; C121481:astringin; D003577:Cytochrome P-450 Enzyme System; D009251:NADPH-Ferrihemoprotein Reductase; C052423:flavocytochrome P450 BM3 monoxygenases; C058229:polydatin
keywords: (E)-Astringin; Bacterial CYP102A1; Biocatalyst; Piceatannol; Regioselective CH hydroxylation; Resveratrol