Gram scale synthesis of specialized pro-resolving mediator 17(S)-HDHA using lipoxygenase enhanced by water-soluble reducing agent TCEP

Bioorg Med Chem Lett. 2016 Jan 15;26(2):343-345. doi: 10.1016/j.bmcl.2015.12.011. Epub 2015 Dec 7.

Abstract

17(S)-Hydroxy docosahexaenoic acid (17(S)-HDHA) is a specialized pro-resolving mediator. The oxidation of docosahexaenoic acid (DHA) to 17(S)-HDHA using soybean lipoxygenase was accomplished in the presence of the reducing agent TCEP in high yield and high enantio excess. We demonstrated application of this strategy to the synthesis of other fatty acids and to gram scale synthesis of 17(S)-HDHA.

Keywords: 17-HDHA; 17-HDoHE; Pro-resolving mediator; Resolvins D series; n-3 PUFA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Borohydrides / chemistry
  • Dithiothreitol / chemistry
  • Docosahexaenoic Acids / chemical synthesis*
  • Docosahexaenoic Acids / chemistry
  • Glycine max
  • Linolenic Acids / chemistry
  • Lipoxygenase / chemistry*
  • Oxidation-Reduction
  • Phosphines / chemistry*
  • Reactive Oxygen Species / chemistry
  • Solubility
  • Stereoisomerism
  • Water / chemistry

Substances

  • Borohydrides
  • Linolenic Acids
  • Phosphines
  • Reactive Oxygen Species
  • Water
  • tris(2-carboxyethyl)phosphine
  • Docosahexaenoic Acids
  • sodium borohydride
  • 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid
  • lipoxygenase L-1
  • Lipoxygenase
  • Dithiothreitol