A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase

Chem Commun (Camb). 2002 Sep 21:(18):2004-5. doi: 10.1039/b206199f.

Abstract

A new, mild and high yielding synthesis of phosphoramidates is described: potassium salts of carboxylic acids are treated with ethylchloroformate and the resulting activated anhydride-carbonates are then treated with LiNH-P(O)(OEt)2 in situ--the methodology is especially suited to acid sensitive systems featuring BOC, tBu or acetal protecting groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / pharmacology
  • Aspartate-Semialdehyde Dehydrogenase / antagonists & inhibitors*
  • Aspartate-Semialdehyde Dehydrogenase / chemistry
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / metabolism
  • Binding Sites
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • Models, Molecular
  • Phosphoric Acids / chemical synthesis*
  • Phosphoric Acids / pharmacology

Substances

  • Amides
  • Bacterial Proteins
  • Enzyme Inhibitors
  • Phosphoric Acids
  • phosphoramidic acid
  • Aspartate-Semialdehyde Dehydrogenase