Evidence for the combined participation of a C10 and a C15 precursor in the biosynthesis of moenocinol, the lipid part of the moenomycin antibiotics

被引:11
作者
Neundorf, I
Köhler, C
Hennig, L
Findeisen, M
Arigoni, D
Welzel, P
机构
[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
[2] Univ Leipzig, Fak Chem & Mineral, D-04103 Leipzig, Germany
关键词
D O I
10.1002/cbic.200300622
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Upon feeding of [2-C-13,4-2H]-1-deoxy-D-xylulose to <LF>Streptomyces ghanaensis, the deuterium label was retained exclusively at positions C-7 and C-17 in the moenocinol part of the moenomycin antibiotics. This result vindicates the hypothesis that the C-25 structure of moenocinol is assembled from a C-10 and a C-15 precursor each of which requires for its formation the involvement of a dimethylallyl diphosphate starter unit.
引用
收藏
页码:1201 / 1205
页数:5
相关论文
共 32 条
  • [1] LytB protein catalyzes the terminal step of the 2-C-methyl-D-erythritol-4-phosphate pathway of isoprenoid biosynthesis
    Altincicek, B
    Duin, EC
    Reichenberg, A
    Hedderich, R
    Kollas, AK
    Hintz, M
    Wagner, S
    Wiesner, J
    Beck, E
    Jomaa, H
    [J]. FEBS LETTERS, 2002, 532 (03) : 437 - 440
  • [2] Dimethylallyl pyrophosphate is not the committed precursor of isopentenyl pyrophosphate during terpenoid biosynthesis from 1-deoxyxylulose in higher plants
    Arigoni, D
    Eisenreich, W
    Latzel, C
    Sagner, S
    Radykewicz, T
    Zenk, MH
    Bacher, A
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (04) : 1309 - 1314
  • [3] BRAUN S, 1998, 150 MOE BASIC NMR EX, P329
  • [4] Deuterium-labelled isotopomers of 2-C-methyl-D-erythritol as tools for the elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis
    Charon, L
    Hoeffler, JF
    Pale-Grosdemange, C
    Lois, LM
    Campos, N
    Boronat, A
    Rohmer, M
    [J]. BIOCHEMICAL JOURNAL, 2000, 346 : 737 - 742
  • [5] On the reduction steps in the mevalonate independent 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for isoprenoid biosynthesis in the bacterium Zymomonas mobilis
    Charon, L
    Pale-Grosdemange, C
    Rohmer, M
    [J]. TETRAHEDRON LETTERS, 1999, 40 (40) : 7231 - 7234
  • [6] Donnerstag A, 1996, MAGN RESON CHEM, V34, P1031, DOI 10.1002/(SICI)1097-458X(199612)34:12<1031::AID-OMR10>3.0.CO
  • [7] 2-7
  • [8] A STRUCTURALLY AND BIOGENETICALLY INTERESTING MOENOMYCIN ANTIBIOTIC
    DONNERSTAG, A
    MARZIAN, S
    MULLER, D
    WELZEL, P
    BOTTGER, D
    STARK, A
    FEHLHABER, HW
    MARKUS, A
    VANHEIJENOORT, Y
    VANHEIJENOORT, J
    [J]. TETRAHEDRON, 1995, 51 (07) : 1931 - 1940
  • [9] Exploratory investigations into the biosynthesis of the antibiotic moenomycin A
    Endler, K
    Schuricht, U
    Hennig, L
    Welzel, P
    [J]. TETRAHEDRON LETTERS, 1998, 39 (1-2) : 13 - 16
  • [10] Biosynthesis of isoprenoids in Escherichia coli:: The fate of the 3-H and 4-H atoms of 1-deoxy-d-xylulose
    Giner, JL
    Jaun, B
    Arigoni, D
    [J]. CHEMICAL COMMUNICATIONS, 1998, (17) : 1857 - 1858