Activating a Cryptic Ansamycin Biosynthetic Gene Cluster To Produce Three New Naphthalenic Octaketide Ansamycins with n-Pentyl and n-Butyl Side Chains

Org Lett. 2015 Aug 7;17(15):3706-9. doi: 10.1021/acs.orglett.5b01686. Epub 2015 Jul 13.

Abstract

Genome mining is a rational approach to discovering new natural products. The genome sequence analysis of Streptomyces sp. LZ35 revealed the presence of a putative ansamycin gene cluster (nam). Constitutive overexpression of the pathway-specific transcriptional regulatory gene nam1 successfully activated the nam gene cluster, and three novel naphthalenic octaketide ansamycins were discovered with unprecedented n-pentylmalonyl-CoA or n-butylmalonyl-CoA extender units. This study represents the first example of discovering novel ansamycin scaffolds via activation of a cryptic gene cluster.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Molecular Structure
  • Multigene Family
  • Rifabutin / chemical synthesis*
  • Rifabutin / chemistry
  • Rifabutin / pharmacology
  • Streptomyces / genetics*

Substances

  • Biological Products
  • Rifabutin