Alkyldihydropyrones, new polyketides synthesized by a type III polyketide synthase from Streptomyces reveromyceticus

Teruki Aizawa, Seung Young Kim, Shunji Takahashi, Masahiko Koshita, Mioka Tani, Yushi Futamura, Hiroyuki Osada, Nobutaka Funa*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Genome sequencing allows a rapid and efficient identification of novel catalysts that produce novel secondary metabolites. Here we describe the catalytic properties of dihydropyrone synthase A (DpyA), a novel type III polyketide synthase encoded in a linear plasmid of Streptomyces reveromyceticus. Heterologous expression of dpyA led to the accumulation of alkyldihydropyrones A (1), B (2), C (3) and D (4), which are novel dihydropyran compounds that exhibit weak cytotoxicity against the leukemia cell line HL-60. DpyA catalyzes the condensation of β-hydroxyl acid thioester and methylmalonyl-CoA to yield a triketide intermediate that then undergoes lactonization of a secondary alcohol and a thioester to give alkyldihydropyrone.

Original languageEnglish
Pages (from-to)819-823
Number of pages5
JournalJournal of Antibiotics
Volume67
Issue number12
DOIs
Publication statusPublished - 2014 Dec 1
Externally publishedYes

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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