Enzymatic synthesis and purification of aromatic coenzyme a esters

Anal Biochem. 2002 Mar 15;302(2):305-12. doi: 10.1006/abio.2001.5574.

Abstract

Two recombinant His-tagged proteins, a plant 4-coumarate:coenzyme A ligase (EC 6.2.1.12) and a bacterial benzoate:coenzyme A ligase (EC 6.2.1.25), were expressed in Escherichia coli and purified in a single step using Ni-chelating chromatography. Purified enzymes were used to synthesize cinnamoyl-coenzyme A (CoA), p-coumaroyl-CoA, feruloyl-CoA, caffeoyl-CoA, and benzoyl-CoA. Conversions up to 95% were achieved. Using a rapid solid-phase extraction procedure, the target CoA esters were isolated with yields of up to 80%. Structures were confirmed by analytical comparison with chemically synthesized reference compounds and electrospray ionization-mass spectrometry. The recombinant enzymes were stable for several months at -80 degrees C, thus providing a reliable and facile method to produce these delicate biological intermediates.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acyl Coenzyme A / biosynthesis*
  • Acyl Coenzyme A / isolation & purification
  • Chromatography, Affinity / methods
  • Coenzyme A Ligases / biosynthesis
  • Coenzyme A Ligases / genetics
  • Coenzyme A Ligases / metabolism*
  • Escherichia coli / genetics
  • Plants / enzymology
  • Recombinant Proteins / biosynthesis
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Reference Standards
  • Rhodopseudomonas / enzymology
  • Spectrometry, Mass, Electrospray Ionization / methods

Substances

  • Acyl Coenzyme A
  • Recombinant Proteins
  • feruloyl-CoA
  • 4-coumaroyl-coenzyme A
  • caffeoyl-coenzyme A
  • benzoyl-coenzyme A
  • cinnamoyl-coenzyme A
  • Coenzyme A Ligases
  • 4-coumarate-CoA ligase
  • benzoate coenzyme A ligase