Structure and biosynthetic implication of (S)-NHAB, a novel shunt product, from a disruptant of the actVI-ORFA gene for actinorhodin biosynthesis in Streptomyces coelicolor A3(2)

Ozawa, Makoto, Taguchi, Takaaki, Itoh, Takayuki, Ebizuka, Yutaka, Booker-Milburn, Kevin I., Stephenson, G. Richard and Ichinose, Koji (2003) Structure and biosynthetic implication of (S)-NHAB, a novel shunt product, from a disruptant of the actVI-ORFA gene for actinorhodin biosynthesis in Streptomyces coelicolor A3(2). Tetrahedron, 59 (44). pp. 8793-8798. ISSN 0040-4020

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Abstract

A novel shunt product was isolated from a disruptant of the actVI-ORFA gene involved in the biosynthesis of actinorhodin (ACT) in Streptomyces coelicolor A3(2). Its structure was elucidated as 1,4-naphthoquinone-8-hydroxy-3-[3(S)-acetoxy-butyric acid], (S)-NHAB, based on NMR, MS. and CD spectroscopic data as well as a single crystal X-ray crystallographic analysis. The formation of (S)-NHAB involves a retro-Claisen type C-C bond cleavage of an ACT biosynthetic intermediate. Feeding experiments with [1-C-13] and [2-C-13] acetates indicated its biosynthetic origin as a single octaketide chain. The relevant gene product, Act-ORFA, which is a functionally unknown protein. is proposed to play a regulatory role related to the multi-enzymatic steps to ACT production, based on the metabolic profile of its disruptant and the wide distribution of actVI-ORFA homologues in the gene clusters for Streptomyces aromatic polyketides. (C) 2003 Elsevier Ltd. All rights reserved.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 08 Jun 2011 11:03
Last Modified: 21 Apr 2020 20:36
URI: https://ueaeprints.uea.ac.uk/id/eprint/32004
DOI: 10.1016/j.tet.2003.09.036

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