Biosynthetic origin of the rare nitroaryl moiety of the polyketide antibiotic aureothin:: Involvement of an unprecedented N-oxygenase

被引:95
作者
He, J [1 ]
Hertweck, C [1 ]
机构
[1] Hans Knoll Inst Nat Prod Res, D-07745 Jena, Germany
关键词
D O I
10.1021/ja039328t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The antibiotic aureothin is a rare natural nitroaromatic compound produced by Streptomyces thioluteus. By labeling experiments, we demonstrate for the first time that p-nitrobenzoate (PNBA) serves as a polyketide synthase starter unit. Cloning, heterologous expression, and inactivation experiments reveal that this unusual primer is synthesized from p-aminobenzoate (PABA) by means of AurF, a novel N-oxygenase. Copyright © 2004 American Chemical Society.
引用
收藏
页码:3694 / 3695
页数:2
相关论文
共 24 条
[1]  
[Anonymous], 2000, ROMPP ENCY NATURAL P
[2]   PYRROLNITRIN NEW ANTIBIOTIC SUBSTANCE PRODUCED BY PSEUDOMONAS [J].
ARIMA, K ;
FUKUTA, A ;
IMANAKA, H ;
KOUSAKA, M ;
TAMURA, G .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1964, 28 (08) :575-&
[3]   The candicidin gene cluster from Streptomyces griseus IMRU 3570 [J].
Campelo, AB ;
Gil, JA .
MICROBIOLOGY-SGM, 2002, 148 :51-59
[4]  
CARDILLO R, 1972, TETRAHEDRON LETT, P4875
[5]   BIOSYNTHESIS OF AUREOTHIN [J].
CARDILLO, R ;
GHIRINGHELLI, D ;
GIANGRASSO, D ;
GRASSELLI, P ;
SANTOPIE.A .
TETRAHEDRON, 1974, 30 (03) :459-461
[6]   Organizational and mutational analysis of a complete FR-008/candicidin gene cluster encoding a structurally related polyene complex [J].
Chen, S ;
Huang, X ;
Zhou, XF ;
Bai, LQ ;
He, J ;
Jeong, KJ ;
Lee, SY ;
Deng, ZX .
CHEMISTRY & BIOLOGY, 2003, 10 (11) :1065-1076
[7]   THE PAB GENE OF STREPTOMYCES-GRISEUS, ENCODING P-AMINOBENZOIC ACID SYNTHASE, IS LOCATED BETWEEN GENES POSSIBLY INVOLVED IN CANDICIDIN BIOSYNTHESIS [J].
CRIADO, LM ;
MARTIN, JF ;
GIL, JA .
GENE, 1993, 126 (01) :135-139
[8]   Identification of a cyclohexylcarbonyl CoA biosynthetic gene cluster and application in the production of doramectin [J].
Cropp, TA ;
Wilson, DJ ;
Reynolds, KA .
NATURE BIOTECHNOLOGY, 2000, 18 (09) :980-983
[9]  
GREEN JM, 1991, J BIOL CHEM, V266, P12972
[10]   PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin [J].
Gust, B ;
Challis, GL ;
Fowler, K ;
Kieser, T ;
Chater, KF .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2003, 100 (04) :1541-1546