Microbial synthesis of trans isomer of eicosapentaenoic acid (EPA) from the chemically synthesized trans isomer of linolenic acid by a delta12 desaturase-defective mutant of Mortierella alpina 1S-4

Biosci Biotechnol Biochem. 2003 May;67(5):1164-7. doi: 10.1271/bbb.67.1164.

Abstract

The mono trans geometrical isomer of eicosapentaenoic acid, 5c,8c,11c,14c,17t-eicosapentaenoic acid (20:5delta5c,8c,11c,14c,17t), was synthesized by fatty acid microbial conversion using a delta12-desaturase defective mutant of an arachidonic acid (AA)-producing fungus, Mortierella alpina 1S-4. The substrate for the bioconversion, a geometrical isomer of linolenic acid, was prepared by isomerization of linseed oil methyl ester by the nitrous acid method, followed by purification on a AgNO3-silica gel column. The structure and double bond geometry were identified after hydrazine reduction followed by permanganate oxidation to 20:5delta5c,8c,11c,14c,17t. The biosynthetic route from 18:3delta6c,9c,12t to 20:5delta5c,8c,11c,14c,17t was presumed to mimic the route from linoleic acid to arachidonic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arachidonic Acid / metabolism
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Eicosapentaenoic Acid / biosynthesis*
  • Fatty Acid Desaturases / genetics*
  • Fatty Acid Desaturases / metabolism*
  • Hydrazines / chemistry
  • Indicators and Reagents
  • Linseed Oil / chemistry
  • Mass Spectrometry
  • Mortierella / enzymology*
  • Mortierella / genetics*
  • Mutation / genetics
  • Mutation / physiology
  • Oxidation-Reduction
  • Silver Nitrate / chemistry
  • Stereoisomerism
  • alpha-Linolenic Acid / chemical synthesis
  • alpha-Linolenic Acid / metabolism*

Substances

  • Hydrazines
  • Indicators and Reagents
  • alpha-Linolenic Acid
  • Arachidonic Acid
  • Linseed Oil
  • Silver Nitrate
  • Eicosapentaenoic Acid
  • Fatty Acid Desaturases
  • delta-12 fatty acid desaturase