Stereochemistry of hydrogen removal from the 'unactivated' C-3 position of 4-hydroxybutyryl-CoA catalysed by 4-hydroxybutyryl-CoA dehydratase

Chem Commun (Camb). 2004 May 21:(10):1210-1. doi: 10.1039/b402322f. Epub 2004 Apr 23.

Abstract

(R)- and (S)-gamma-[3-(2)H(1)]butyrolactones have been synthesised from (R)- and (S)-glycidol, respectively, and used to demonstrate that it is the pro-(S) hydrogen atom that is stereospecifically abstracted from C-3 of 4-hydroxybutyryl-CoA by 4-hydroxybutyryl-CoA dehydratase, and that this atom is not returned to C-4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydro-Lyases / analysis
  • Hydro-Lyases / chemistry*
  • Hydrogen / analysis
  • Hydrogen / chemistry*
  • Molecular Conformation

Substances

  • Hydrogen
  • 4-hydroxybutyryl-CoA dehydratase
  • Hydro-Lyases