Colibactin biosynthesis and biological activity depend on the rare aminomalonyl polyketide precursor

被引：48

作者：

Brachmann, A. O. ^{[1
]}

Garcie, C. ^{[2
,3
,4
]}

Wu, V. ^{[1
]}

Martin, P. ^{[2
,3
,4
]}

Ueoka, R. ^{[1
]}

Oswald, E. ^{[2
,3
,4
]}

Piel, J. ^{[1
]}

机构：

[1] ETH, Inst Microbiol, CH-8093 Zurich, Switzerland

[2] INSERM, UMR1043, CNRS, INRA,USC 1360, F-31000 Toulouse, France

[3] Univ Toulouse 3, F-31000 Toulouse, France

[4] CHU Toulouse, Serv Bacteriol Hyg, F-31000 Toulouse, France

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 66期

关键词：

PRODRUG ACTIVATION MECHANISM; CARRIER PROTEIN ACP; GENE-CLUSTER; IN-VIVO; ACID; ZWITTERMICIN; RECOGNITION;

D O I：

10.1039/c5cc02718g

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

The as-yet unidentified E. coli metabolite colibactin induces DNA damage in eukaryotic cells and promotes tumorigenesis. Its wide distribution in pathogenic and probiotic strains has raised great interest in its structure and biosynthesis. Here we show that colibactin formation involves a rare aminomalonyl unit used as a building block.

引用

收藏

页码：13138 / 13141

页数：4

相关论文

共 30 条

[1]

Two more pieces of the colibactin genotoxin puzzle from Escherichia coli show incorporation of an unusual 1-aminocyclopropanecarboxylic acid moiety [J].

Bian, Xiaoying ;

Plaza, Alberto ;

Zhang, Youming ;

Mueller, Rolf .

CHEMICAL SCIENCE, 2015, 6 (05) :3154-3160

[2]

In Vivo Evidence for a Prodrug Activation Mechanism during Colibactin Maturation [J].

Bian, Xiaoying ;

Fu, Jun ;

Plaza, Alberto ;

Herrmann, Jennifer ;

Pistorius, Dominik ;

Stewart, A. Francis ;

Zhang, Youming ;

Mueller, Rolf .

CHEMBIOCHEM, 2013, 14 (10) :1194-1197

[3]

The genus Pseudovibrio contains metabolically versatile bacteria adapted for symbiosis [J].

Bondarev, Vladimir ;

Richter, Michael ;

Romano, Stefano ;

Piel, Joern ;

Schwedt, Anne ;

Schulz-Vogt, Heide N. .

ENVIRONMENTAL MICROBIOLOGY, 2013, 15 (07) :2095-2113

[4]

Isolation of a Metabolite from the pks Island Provides Insights into Colibactin Biosynthesis and Activity (vol 17, pg 1545, 2015) [J].

Brotherton, Carolyn A. ;

Wilson, Matthew ;

Byrd, Gary ;

Balskus, Emily P. .

ORGANIC LETTERS, 2015, 17 (09) :2294-2294

[5]

A Prodrug Resistance Mechanism Is Involved in Colibactin Biosynthesis and Cytotoxicity [J].

Brotherton, Carolyn A. ;

Balskus, Emily P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (09) :3359-3362

[6]

Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains [J].

Challis, GL ;

Ravel, J ;

Townsend, CA .

CHEMISTRY & BIOLOGY, 2000, 7 (03) :211-224

[7]

Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type I polyketide synthase extender units [J].

Chan, Yolande A. ;

Boyne, Michael T., II ;

Podevels, Angela M. ;

Klimowicz, Amy K. ;

Handelsman, Jo ;

Kelleher, Neil L. ;

Thomas, Michael G. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (39) :14349-14354

[8]

Recognition of (2S)-Aminomalonyl-Acyl Carrier Protein (ACP) and (2R)-Hydroxymalonyl-ACP by Acyltransferases in Zwittermicin A Biosynthesis [J].

Chan, Yolande A. ;

Thomas, Michael G. .

BIOCHEMISTRY, 2010, 49 (17) :3667-3677

[9]

Bacterial genotoxin colibactin promotes colon tumour growth by inducing a senescence-associated secretory phenotype [J].

Cougnoux, Antony ;

Dalmasso, Guillaume ;

Martinez, Ruben ;

Buc, Emmanuel ;

Delmas, Julien ;

Gibold, Lucie ;

Sauvanet, Pierre ;

Darcha, Claude ;

Dechelotte, Pierre ;

Bonnet, Mathilde ;

Pezet, Denis ;

Wodrich, Harald ;

Darfeuille-Michaud, Arlette ;

Bonnet, Richard .

GUT, 2014, 63 (12) :1932-1942

[10]

Analysis of Structure-Function Relationships in the Colibactin-Maturating Enzyme ClbP [J].

Cougnoux, Antony ;

Gibold, Lucie ;

Robin, Frederic ;

Dubois, Damien ;

Pradel, Nathalie ;

Darfeuile-Michaud, Arlette ;

Dalmasso, Guillaume ;

Delmas, Julien ;

Bonnet, Richard .

JOURNAL OF MOLECULAR BIOLOGY, 2012, 424 (3-4) :203-214