Cycloheximide and actiphenol production in Streptomyces sp. YIM56141 governed by single biosynthetic machinery featuring an acyltransferase-less type I polyketide synthase

  • Org Lett. 2014 Jun 6;16(11):3072-5. doi: 10.1021/ol501179w.
Min Yin  1 ,  Yijun Yan ,  Jeremy R Lohman ,  Sheng-Xiong Huang ,  Ming Ma ,  Guang-Rong Zhao ,  Li-Hua Xu ,  Wensheng Xiang ,  Ben Shen
Affiliations
  • 1. Department of Chemistry, ⊥Department of Molecular Therapeutics, and ¶Natural Products Library Initiative, The Scripps Research Institute , Jupiter, Florida 33458, United States.
PMID: 24815182 DOI: 10.1021/ol501179w
Abstract

Cycloheximide (1) and actiphenol (2) have been isolated from numerous Streptomyces species. Cloning, Sequencing, and characterization of a gene cluster from Streptomyces sp. YIM65141 now establish that 1 and 2 production is governed by single biosynthetic machinery. Biosynthesis of 1 features an acyltransferase-less type I polyketide synthase to construct its carbon backbone but may proceed via 2 as a key intermediate, invoking a provocative reduction of a phenol to a cyclohexanone moiety in natural product biosynthesis.

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