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)

Makoto Ozawa; Takaaki Taguchi; Takayuki Itoh; Yutaka Ebizuka; Kevin I. Booker-Milburn; G. Richard Stephenson; Koji Ichinose

doi:10.1016/j.tet.2003.09.036

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)

Makoto Ozawa, Takaaki Taguchi, Takayuki Itoh, Yutaka Ebizuka, Kevin I. Booker-Milburn, G. Richard Stephenson, Koji Ichinose

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8793-8798
Number of pages	6
Journal	Tetrahedron
Volume	59
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2003.09.036
Publication status	Published - 2003

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10.1016/j.tet.2003.09.036

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@article{81973341924d496c96e94ef40292ef72,

title = "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)",

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.",

author = "Makoto Ozawa and Takaaki Taguchi and Takayuki Itoh and Yutaka Ebizuka and Booker-Milburn, {Kevin I.} and Stephenson, {G. Richard} and Koji Ichinose",

year = "2003",

doi = "10.1016/j.tet.2003.09.036",

language = "English",

volume = "59",

pages = "8793--8798",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "44",

}

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T1 - 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)

AU - Ozawa, Makoto

AU - Taguchi, Takaaki

AU - Itoh, Takayuki

AU - Ebizuka, Yutaka

AU - Booker-Milburn, Kevin I.

AU - Stephenson, G. Richard

AU - Ichinose, Koji

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2003.09.036

DO - 10.1016/j.tet.2003.09.036

M3 - Article

VL - 59

SP - 8793

EP - 8798

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 44

ER -