Halogenation of Unactivated Carbon Centers in Natural Product Biosynthesis: Trichlorination of Leucine during Barbamide Biosynthesis
- 1 March 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (12) , 3900-3901
- https://doi.org/10.1021/ja060151n
Abstract
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.Keywords
This publication has 17 references indexed in Scilit:
- Cryptic chlorination by a non-haem iron enzyme during cyclopropyl amino acid biosynthesisNature, 2005
- Natural Organohalogens: A New Frontier for Medicinal Agents?Journal of Chemical Education, 2004
- Fe(II)/α-Ketoglutarate-Dependent Hydroxylases and Related EnzymesCritical Reviews in Biochemistry and Molecular Biology, 2004
- The First Direct Characterization of a High-Valent Iron Intermediate in the Reaction of an α-Ketoglutarate-Dependent Dioxygenase: A High-Spin Fe(IV) Complex in Taurine/α-Ketoglutarate Dioxygenase (TauD) from Escherichia coliBiochemistry, 2003
- 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 unitGene, 2002
- The Mechanism-based Inactivation of 2,3-Dihydroxybiphenyl 1,2-Dioxygenase by Catecholic SubstratesJournal of Biological Chemistry, 2002
- Neomangicols: Structures and Absolute Stereochemistries of Unprecedented Halogenated Sesterterpenes from a Marine Fungus of the Genus FusariumThe Journal of Organic Chemistry, 1998
- Biosynthesis of the Marine Cyanobacterial Metabolite Barbamide. 1. Origin of the Trichloromethyl GroupJournal of the American Chemical Society, 1998
- Characterization of Sfp, a Bacillus subtilis Phosphopantetheinyl Transferase for Peptidyl Carrier Protein Domains in Peptide SynthetasesBiochemistry, 1998
- Barbamide, a Chlorinated Metabolite with Molluscicidal Activity from the Caribbean Cyanobacterium Lyngbya majusculaJournal of Natural Products, 1996