Biosynthesis of Trehangelin in Polymorphospora rubra K07–0510: Identification of Metabolic Pathway to Angelyl-CoA

Yuki Inahashi, Taro Shiraishi, Kaia Palm, Yoko Takahashi, Satoshi Ōmura, Tomohisa Kuzuyama, Takuji Nakashima

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Trehangelins are trehalose angelates discovered from endophytic actinomycete Polymorphospora rubra K07-0510. We identified the trehangelin biosynthetic gene cluster, including genes that encode a glycoside hydrolase-like protein (thgC), α-amylase (thgD), 3-ketoacyl-ACP synthase III (thgI), 3-ketoacyl-ACP reductase (thgK), enoyl-CoA hydratase (thgH) and acyl transferase (thgJ). Heterologous expression of thgH, thgI, thgJ and thgK confirmed the importance of these genes in the biosynthesis of trehangelin A. Enzymatic activity studies showed that ThgI catalyses the condensation of acetyl-CoA and methylmalonyl-CoA to 2-methylacetoacetyl-CoA (MAA-CoA), ThgK catalyses NADPH-dependent reduction of MAA-CoA to 3-hydroxy-2-methylbutyryl-CoA (HMB-CoA) and ThgH catalyses the dehydration of HMB-CoA to angelyl-CoA (AN-CoA). This is the first report on the elucidation of the enzymatic formation of AN-CoA.

Original languageEnglish
Pages (from-to)1442-1447
Number of pages6
JournalChemBioChem
DOIs
Publication statusPublished - 2016 Aug 3
Externally publishedYes

Keywords

  • angelate
  • angelyl-CoA
  • biosynthesis
  • endophytic actinomycete
  • natural products
  • trehangelin

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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