Chemical variation from the neoantimycin depsipeptide assembly line.

Bioorg Med Chem Lett

Department of Biochemistry and Biomedical Sciences, MG DeGroote Institute for Infectious Disease Research, McMaster University, Hamilton, Ontario, Canada.

Published: September 2013

Here we report the biosynthetic pathway for the neoantimycin and present three novel neoantimycin analogues, neoantimycin D (1), E (2) and F (3), from this assembly system from Streptoverticillium orinoci. Identification of these novel neoantimycin variants was achieved by selective MS/MS interrogation of natural product extracts using diagnostic fragments of the known neoantimycins. Their structures, including the absolute configurations, were elucidated using a combination of NMR experiments, detailed MS/MS experiments and the advanced Marfey's method. The biosynthetic pathway of neoantimycin was dissected by genome sequencing data analysis for the first time, which includes a hybrid nonribosomal peptide synthetase (NRPS) and polyketide synthetase (PKS) assembly lines.

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http://dx.doi.org/10.1016/j.bmcl.2013.07.031DOI Listing

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