Halogenation of unactivated carbon centers in natu...[J Am Chem Soc. 2006]

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1: J Am Chem Soc. 2006 Mar 29;128(12):3900-1. Links

Halogenation of unactivated carbon centers in natural product biosynthesis: trichlorination of leucine during barbamide biosynthesis.

Galonić DP, Vaillancourt FH, Walsh CT.

Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115, USA.

The in vitro reconstitution of leucine halogenation during barbamide biosynthesis has been accomplished. It has been demonstrated that the triple chlorination of the unactivated pro-R methyl group of the peptidyl carrier protein-tethered l-Leu substrate is carried out by the tandem action of two nonheme iron(II)-dependent halogenases, BarB1 and BarB2. Investigation of the substrate specificities of each of the halogenating enzymes revealed their complementary roles in the generation of trichloroleucine.

PMID: 16551084 [PubMed - indexed for MEDLINE]

Characterization of the initial enzymatic steps of barbamide biosynthesis.
J Nat Prod. 2006 Jun; 69(6):938-44.

[J Nat Prod. 2006]
The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit.
Gene. 2002 Aug 21; 296(1-2):235-47.

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ReviewFlavin-dependent halogenases involved in secondary metabolism in bacteria.
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[Appl Microbiol Biotechnol. 2006]
ReviewCatalytic mechanisms, basic roles, and biotechnological and environmental significance of halogenating enzymes.
Acta Biochim Biophys Sin (Shanghai). 2008 Mar; 40(3):183-93.

[Acta Biochim Biophys Sin (Shanghai). 2008]
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Cited by 5 PubMed Central articles

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Cadel-Six S, Dauga C, Castets AM, Rippka R, Bouchier C, Tandeau de Marsac N, Welker M. Mol Biol Evol. 2008 Sep; 25(9):2031-41. Epub 2008 Jul 8.

[Mol Biol Evol. 2008]
Biosynthetic origin of natural products isolated from marine microorganism-invertebrate assemblages.
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[Proc Natl Acad Sci U S A. 2007]
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