Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases

Ryotaro Hara, Naoko Uchiumi, Naoko Okamoto, Kuniki Kino

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to L-proline and L-pipecolinic acid, we found that 3,4-dehydro-L-proline, L-azetidine-2-carboxylic acid, cis-3-hydroxy-L-proline, and L-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-L-proline, cis-3-hydroxy-L-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-L-proline.

Original languageEnglish
Pages (from-to)1384-1388
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume78
Issue number8
DOIs
Publication statusPublished - 2014

Keywords

  • Dihydroxyproline
  • Dioxygenase
  • Hydroxylase
  • Oxygenation
  • Proline derivative

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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