Regio- and Stereoselective Oxidative Phenol Coupling in Aspergillus niger

被引：63
作者：
Girol, Christian Gil [1 ]
Fisch, Katja M. [2 ]
Heinekamp, Thorsten [4 ]
Guenther, Stefan [1 ]
Huettel, Wolfgang [1 ]
Piel, Joern [3 ]
Brakhage, Axel A. [4 ]
Mueller, Michael [1 ]
机构：
[1] Univ Freiburg, Inst Pharmazeut Wissensch, D-79104 Freiburg, Germany
[2] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[3] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
[4] Leibniz Inst Nat Prod Res & Infect Biol, Dept Mol & Appl Microbiol, D-07745 Jena, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 39期
关键词：
biaryls; biosynthesis; C?C coupling; natural products; polyketides; DIRIGENT PROTEIN; BICOUMARINS; KOTANIN; BIOSYNTHESIS; METABOLITES; SCLEROTIA; PRODUCTS; LACCASE; GENES;
D O I：
10.1002/anie.201203603
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Piecing it together: Aspergillus niger produces kotanin (see structure) by dimerization of the monomeric, polyketide-synthase-derived (PKS) 7-demethylsiderin. A combined approach, comprising bioinformatics and gene-deletion experiments, identified the biosynthetic cluster responsible for kotanin production. Homology modeling and substrate docking provide a rationale for the regio- and stereoselective phenol coupling reaction. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9788 / 9791
页数：4
相关论文
共 31 条
  • [1] [Anonymous], 2010, GLID VERS 5 6
  • [2] BUCHI G, 1971, J ORG CHEM, V36, P1143
  • [3] BUCHI G, 1977, J ORG CHEM, V42, P244, DOI 10.1021/jo00422a015
  • [4] Polyketides, proteins and genes in fungi: programmed nano-machines begin to reveal their secrets
    Cox, Russell J.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (13) : 2010 - 2026
  • [5] ORLANDIN - NONTOXIC FUNGAL METABOLITE WITH PLANT-GROWTH INHIBITING PROPERTIES
    CUTLER, HG
    CRUMLEY, FG
    COX, RH
    HERNANDEZ, O
    COLE, RJ
    DORNER, JW
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1979, 27 (03) : 592 - 595
  • [6] Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center
    Davin, LB
    Wang, HB
    Crowell, AL
    Bedgar, DL
    Martin, DM
    Sarkanen, S
    Lewis, NG
    [J]. SCIENCE, 1997, 275 (5298) : 362 - 366
  • [7] Chemical induction of silent biosynthetic pathway transcription in Aspergillus niger
    Fisch, K. M.
    Gillaspy, A. F.
    Gipson, M.
    Henrikson, J. C.
    Hoover, A. R.
    Jackson, L.
    Najar, F. Z.
    Waegele, H.
    Cichewicz, R. H.
    [J]. JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY, 2009, 36 (09) : 1199 - 1213
  • [8] BIOSYNTHESIS AND CONSTITUTION OF LIGNIN
    FREUDENBERG, K
    [J]. NATURE, 1959, 183 (4669) : 1152 - 1155
  • [9] PURIFICATION AND PROPERTIES OF DIHYDROGEODIN OXIDASE FROM ASPERGILLUS-TERREUS
    FUJII, I
    IIJIMA, H
    TSUKITA, S
    EBIZUKA, Y
    SANKAWA, U
    [J]. JOURNAL OF BIOCHEMISTRY, 1987, 101 (01) : 11 - 18
  • [10] New natural products from the sponge-derived fungus Aspergillus niger
    Hiort, J
    Maksimenka, K
    Reichert, M
    Perovic-Ottstadt, S
    Lin, WH
    Wray, V
    Steube, K
    Schaumann, K
    Weber, H
    Proksch, P
    Ebel, R
    Müiller, WEG
    Bringmann, G
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (09): : 1532 - 1543
1234