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A heptaketide naphthaldehyde produced by a polyketide synthase from Nectria haematococca

Bostrycoidin and fusarubin are biologically active fungal polyketides produced by . This azaanthraquinone and naphthoquinone are thought to be biosynthesized via formation of a C heptaketide aldehyde as a common key intermediate. A BLAST search against the genome of revealed one candidate gene (NECH... Full description

Journal Title: Bioorganic & Medicinal Chemistry Letters 01 July 2012, Vol.22(13), pp.4338-4340
Main Author: Awakawa, Takayoshi
Other Authors: Kaji, Takuya , Wakimoto, Toshiyuki , Abe, Ikuro
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0960-894X ; E-ISSN: 1464-3405 ; DOI: 10.1016/j.bmcl.2012.05.005
Link: https://www.sciencedirect.com/science/article/pii/S0960894X12005951
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recordid: elsevier_sdoi_10_1016_j_bmcl_2012_05_005
title: A heptaketide naphthaldehyde produced by a polyketide synthase from Nectria haematococca
format: Article
creator:
  • Awakawa, Takayoshi
  • Kaji, Takuya
  • Wakimoto, Toshiyuki
  • Abe, Ikuro
subjects:
  • Biosynthesis
  • Polyketide
  • Polyketide Synthase
  • Azaanthraquinone
  • Bostrycoidin
  • Medicine
  • Chemistry
  • Anatomy & Physiology
ispartof: Bioorganic & Medicinal Chemistry Letters, 01 July 2012, Vol.22(13), pp.4338-4340
description: Bostrycoidin and fusarubin are biologically active fungal polyketides produced by . This azaanthraquinone and naphthoquinone are thought to be biosynthesized via formation of a C heptaketide aldehyde as a common key intermediate. A BLAST search against the genome of revealed one candidate gene (NECHADRAFT_101778, NhPKS1), which encodes a multi-domain polyketide synthase (PKS) with a thiol reductase (TR) domain that would facilitate the reductive release of the intermediate to produce a free aldehyde. To investigate the possible involvement of NhPKS1 in the biosynthesis of bostrycoidin and fusarubin, NhPKS1 was heterologously expressed in , and shown to produce a heptaketide 3-acetonyl-1,6,8-trihydroxy-2-naphthaldehyde as a single product. Thus, NhPKS1 catalyzes a C-2/C-11 and C-4/C-9 aldol-type cyclization of a linear intermediate followed by a subsequent reductive product release to yield the naphthaldehyde....
language: eng
source:
identifier: ISSN: 0960-894X ; E-ISSN: 1464-3405 ; DOI: 10.1016/j.bmcl.2012.05.005
fulltext: fulltext
issn:
  • 0960-894X
  • 0960894X
  • 1464-3405
  • 14643405
url: Link


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titleA heptaketide naphthaldehyde produced by a polyketide synthase from Nectria haematococca
creatorAwakawa, Takayoshi ; Kaji, Takuya ; Wakimoto, Toshiyuki ; Abe, Ikuro
ispartofBioorganic & Medicinal Chemistry Letters, 01 July 2012, Vol.22(13), pp.4338-4340
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subjectBiosynthesis ; Polyketide ; Polyketide Synthase ; Azaanthraquinone ; Bostrycoidin ; Medicine ; Chemistry ; Anatomy & Physiology
descriptionBostrycoidin and fusarubin are biologically active fungal polyketides produced by . This azaanthraquinone and naphthoquinone are thought to be biosynthesized via formation of a C heptaketide aldehyde as a common key intermediate. A BLAST search against the genome of revealed one candidate gene (NECHADRAFT_101778, NhPKS1), which encodes a multi-domain polyketide synthase (PKS) with a thiol reductase (TR) domain that would facilitate the reductive release of the intermediate to produce a free aldehyde. To investigate the possible involvement of NhPKS1 in the biosynthesis of bostrycoidin and fusarubin, NhPKS1 was heterologously expressed in , and shown to produce a heptaketide 3-acetonyl-1,6,8-trihydroxy-2-naphthaldehyde as a single product. Thus, NhPKS1 catalyzes a C-2/C-11 and C-4/C-9 aldol-type cyclization of a linear intermediate followed by a subsequent reductive product release to yield the naphthaldehyde....
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