Elucidating hydroxylation and methylation steps tailoring piericidin A1 biosynthesis

Yaolong Chen; Wenjun Zhang; Yiguang Zhu; Qingbo Zhang; Xinpeng Tian; Si Zhang; Changsheng Zhang

doi:10.1021/ol4034176

Elucidating hydroxylation and methylation steps tailoring piericidin A1 biosynthesis

Org Lett. 2014 Feb 7;16(3):736-9. doi: 10.1021/ol4034176. Epub 2014 Jan 10.

Authors

Yaolong Chen¹, Wenjun Zhang, Yiguang Zhu, Qingbo Zhang, Xinpeng Tian, Si Zhang, Changsheng Zhang

Affiliation

¹ Key Laboratory of Tropical Marine Bio-resources and Ecology, RNAM Center for Marine Microbiology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences , 164 West Xingang Road, Guangzhou 510301, China.

PMID: 24409990
DOI: 10.1021/ol4034176

Abstract

The piericidin A1 (1) gene cluster was identified from the deep-sea derived Streptomyces sp. SCSIO 03032. Our in vivo and in vitro experiments verified PieE as a 4'-hydroxylase and PieB2 as a 4'-O-methyltransferase, allowing the elucidation of the post-PKS modification steps involved in 1 biosynthesis. In addition, the shunt metabolite piericidin E1 (7) was identified as a novel analogue featuring a C-2/C-3 epoxy ring.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / metabolism
Hydroxylation
Methylation
Methyltransferases / chemistry*
Methyltransferases / metabolism
Molecular Structure
Multigene Family
Pyridines / chemical synthesis*
Pyridines / metabolism
Streptomyces / chemistry*
Streptomyces / genetics
Streptomyces / metabolism

Substances

Anti-Bacterial Agents
Pyridines
piericidin A
Methyltransferases