A heptaketide naphthaldehyde produced by a polyketide synthase from Nectria haematococca

Takayoshi Awakawa, Takuya Kaji, Toshiyuki Wakimoto, Ikuro Abe

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Bostrycoidin and fusarubin are biologically active fungal polyketides produced by Nectria haematococca. This azaanthraquinone and naphthoquinone are thought to be biosynthesized via formation of a C 14 heptaketide aldehyde as a common key intermediate. A BLAST search against the genome of N. haematococca 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 Aspergillus oryzae, 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. The results indicate NhPKS1 is the enzyme involved in the biosynthesis of bostrycoidin and fusarubin.

Original languageEnglish
Pages (from-to)4338-4340
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number13
DOIs
Publication statusPublished - 2012 Jul 1
Externally publishedYes

Keywords

  • Azaanthraquinone
  • Biosynthesis
  • Bostrycoidin
  • Polyketide
  • Polyketide synthase

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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