On the stereochemistry of 2-hydroxyethylphosphonate dioxygenase

J Am Chem Soc. 2011 Mar 30;133(12):4236-9. doi: 10.1021/ja1113326. Epub 2011 Mar 7.


Stereochemical investigations have shown that the conversion of 2-hydroxyethylphosphonate to hydroxymethylphosphonate by the enzyme HEPD involves removal of the pro-S hydrogen at C2 and, surprisingly, the loss of stereochemical information at C1. As a result, the mechanisms previously proposed for HEPD must be re-evaluated.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dioxygenases / chemistry*
  • Dioxygenases / metabolism
  • Molecular Structure
  • Organophosphonates / chemistry*
  • Stereoisomerism


  • 2-hydroxyethyl phosphonate
  • Organophosphonates
  • Dioxygenases