Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete.

Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Research Abstract Details 

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Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Abstract Text:

Masashi Ueki,Danica P Galoni?, Vaillancourt,Sylvie Garneau-Tsodikova,Ellen Yeh,David A Vosburg,Frank C Schroeder,Hiroyuki Osada,Christopher T Walsh,

Four adjacent open reading frames, cytC1-C4, were cloned from a cytotrienin-producing strain of a Streptomyces sp. by using primers derived from the conserved region of a gene encoding a nonheme iron halogenase, CmaB, in coronamic acid biosynthesis. CytC1-3 were active after expression in Escherichia coli, and CytC4 was active after expression in Pseudomonas putida. CytC1, a relatively promiscuous adenylation enzyme, installs the aminoacyl moieties on the phosphopantetheinyl arm of the holo carrier protein CytC2. CytC3 is a nonheme iron halogenase that will generate both gamma-chloro- and gamma,gamma-dichloroaminobutyryl-S-CytC2 from aminobutyryl-S-CytC2. CytC4, a thioesterase, hydrolytically releases the dichloroaminobutyrate, a known streptomycete antibiotic. Thus, this short four-protein pathway is likely the biosynthetic source of this amino acid antimetabolite. This four-enzyme system analogously converts the proS-methyl group of valine to the dichloromethyl product regio- and stereospecifically.

Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Publishing Authors By Initials

M Ueki,DP Galoni?,FH Vaillancourt,S Garneau-Tsodikova,E Yeh,DA Vosburg,FC Schroeder,H Osada,CT Walsh,

For similar bacteria: endospore-forming bacteria: gram-positive endospore-forming bacteria: gram-positive endospore-forming rods: streptomycetaceae: streptomyces research abstracts see: bacteria: endospore-forming bacteria: gram-positive endospore-forming bacteria: gram-positive endospore-forming rods: streptomycetaceae: streptomyces research

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Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Chemistry & biology

VOLUME: 13

Page Numbers: 1183-91

Journal Abbreviation: Chem. Biol.

ISSN: 1074-5521

DAY: 3

MONTH: Nov

YEAR: 2006

Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 9500160

Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Keywords Mesh Terms:

KEYWORDS: Streptomyces

MESH TERMS: metabolism

Chemical & Substance for Abstract: Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Information

Substance Name: non-ribosomal peptide synthase

Registry Number: EC 6.3.2.-

Grant and Affiliation Information for Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete.

AFFILIATION: Antibiotics Laboratory, RIKEN Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.

Country: England

AGENCY: United States NIGMS

GRANT: GM 49338

ACRONYM: GM

MEDLINETA: Chem Biol

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