Efficient synthesis of radiolabeled propionyl-coenzyme A and acetyl-coenzyme A

Anal Biochem. 1995 Jan 1;224(1):159-62. doi: 10.1006/abio.1995.1022.

Abstract

The efficient microscale synthesis of [1-14C]propionyl-CoA from commercially available sodium [1-14C]-propionate using 1,1'-carbonyldiimidazole in yields of nearly 70% is reported for the first time. A substantial improvement in the process for making [1-14C]acetyl-CoA from sodium [1-14C]acetate was also achieved. Yields of greater than 90% were consistently obtained for the latter synthesis. The salt-free CoA-thioesters were obtained in homogenous form by reverse-phase HPLC. The products were judged to be pure by 1H NMR analysis: neither iso-CoA analogs nor contaminants frequently found in commercial samples could be detected. The samples of acetyl- and propionyl-CoA were shown to be radiochemically pure by HPLC and by analysis of the products of incubations with acetyl- and propionyl-CoA carboxylase. This highly efficient synthesis is a cost-effective method for the preparation of radiolabeled CoA thioesters and can easily be adapted to the production of other acyl-CoA analogs.

Publication types

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

MeSH terms

  • Acetyl Coenzyme A / chemical synthesis*
  • Acyl Coenzyme A / chemical synthesis*
  • Carbon Radioisotopes
  • Isotope Labeling*

Substances

  • Acyl Coenzyme A
  • Carbon Radioisotopes
  • propionyl-coenzyme A
  • Acetyl Coenzyme A