Identification of a set of genes involved in the formation of the substrate for the incorporation of the unusual "glycolate" chain extension unit in ansamitocin biosynthesis

被引:59
作者
Carroll, BJ [1 ]
Moss, SJ [1 ]
Bai, LQ [1 ]
Kato, Y [1 ]
Toelzer, S [1 ]
Yu, TW [1 ]
Floss, HG [1 ]
机构
[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA
关键词
D O I
10.1021/ja0124764
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The unusual "glycolate" extender unit at C-9/C-10 of ansamitocin is not derived from 2-hydroxymalonyl-CoA or 2-methoxymalonyl-CoA, as demonstrated by feeding experiments with the corresponding 1-13C-labeled N-acetylcysteamine thioesters but is formed from an acyl carrier protein (ACP)-bound substrate, possibly 2-methoxymalonyl-ACP, elaborated by enzymes encoded by a subcluster of five genes, asm12-17, from the ansamitocin bisosynthetic gene cluster. Copyright © 2002 American Chemical Society.
引用
收藏
页码:4176 / 4177
页数:2
相关论文
共 22 条
  • [1] ISOLATION, CHEMICAL CHARACTERIZATION AND STRUCTURE OF ANSAMITOCIN, A NEW ANTI-TUMOR ANSAMYCIN ANTIBIOTIC
    ASAI, M
    MIZUTA, E
    IZAWA, M
    HAIBARA, K
    KISHI, T
    [J]. TETRAHEDRON, 1979, 35 (09) : 1079 - 1085
  • [2] BINDSEIL KU, 1994, LIEBIGS ANN CHEM, P305
  • [3] Byrne K. M., 1993, DEV IND MICROBIOL, V32, P29
  • [4] MACROLIDE BIOSYNTHESIS .4. INTACT INCORPORATION OF A CHAIN-ELONGATION INTERMEDIATE INTO ERYTHROMYCIN
    CANE, DE
    YANG, CC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1255 - 1257
  • [5] Aminoacyl-S-enzyme intermediates in β-hydroxylations and α,β-desaturations of amino acids in peptide antibiotics
    Chen, HW
    Thomas, MG
    O'Connor, SE
    Hubbard, BK
    Burkart, MD
    Walsh, CT
    [J]. BIOCHEMISTRY, 2001, 40 (39) : 11651 - 11659
  • [6] Coumarin formation in novobiocin biosynthesis:: β-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI
    Chen, HW
    Walsh, CT
    [J]. CHEMISTRY & BIOLOGY, 2001, 8 (04): : 301 - 312
  • [7] BIOSYNTHETIC ORIGIN OF C2 UNITS OF GELDANAMYCIN AND DISTRIBUTION OF LABEL FROM D-[6-13C]GLUCOSE
    HABER, A
    JOHNSON, RD
    RINEHART, KL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) : 3541 - 3544
  • [8] FERMENTATIVE PRODUCTION AND BIOSYNTHESIS OF ANSAMITOCINS .2. BIOSYNTHETIC ORIGIN OF THE ANSA-STRUCTURE OF ANSAMITOCIN P-3
    HATANO, K
    MIZUTA, E
    AKIYAMA, S
    HIGASHIDE, E
    NAKAO, Y
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1985, 49 (02): : 327 - 333
  • [9] BIOSYNTHETIC ORIGIN OF AMINOBENZENOID NUCLEUS (C7N-UNIT) OF ANSAMITOCIN, A GROUP OF NOVEL MAYTANSINOID ANTIBIOTICS
    HATANO, K
    AKIYAMA, SI
    ASAI, M
    RICKARDS, RW
    [J]. JOURNAL OF ANTIBIOTICS, 1982, 35 (10) : 1415 - 1417
  • [10] ANSAMITOCIN, A GROUP OF NOVEL MAYTANSINOID ANTIBIOTICS WITH ANTITUMOUR PROPERTIES FROM NOCARDIA
    HIGASHIDE, E
    ASAI, M
    OOTSU, K
    TANIDA, S
    KOZAI, Y
    HASEGAWA, T
    KISHI, T
    SUGINO, Y
    YONEDA, M
    [J]. NATURE, 1977, 270 (5639) : 721 - 722