Monoamine oxidase and transaminase screening: biotransformation of 2-methyl-6-alkylpiperidines by Neopestalotiopsis sp. CBMAI 2030

Appl Microbiol Biotechnol. 2017 Aug;101(15):6061-6070. doi: 10.1007/s00253-017-8389-z. Epub 2017 Jun 28.

Abstract

High-throughput screening detected transaminases (TAs) and monoamine oxidases (MAOs) in fungi by applying a fluorogenic probe. Strains F026, F037, F041, F053, and F057 showed the highest enzymatic conversions (31, 60, 30, 40, and 32%, respectively) and where evaluated for their ability to transform piperidines. Strain F053 (Neopestalotiopsis sp. CBMAI 2030) revealed unusual enzymatic activity to deracemize 2-methyl-6-alkylpiperidines. Neopestalotiopsis sp. CBMAI 2030 was capable to convert 2-methyl-6-propylpiperidine, 2-methyl-6-butylpiperidine, and 2-methyl-6-pentylpiperidine in piperideine with 11, 14, and 24% conversion, respectively. The activity was enhanced by cultivating the fungus with 2-methyl-6-pentylpiperidine (38% conversion and 73% ee).

Keywords: Chiral amines; Fluorogenic probes; High-throughput screening; Monoamine oxidase; Piperidines; Transaminase.

MeSH terms

  • Amines / metabolism
  • Ascomycota / enzymology*
  • Biotransformation*
  • Fluorescent Dyes
  • High-Throughput Screening Assays
  • Monoamine Oxidase / metabolism*
  • Piperidines / chemistry
  • Piperidines / metabolism*
  • Stereoisomerism
  • Transaminases / metabolism*

Substances

  • Amines
  • Fluorescent Dyes
  • Piperidines
  • Monoamine Oxidase
  • Transaminases