Unit

UNIT 15.1 Synthesis of Amino Acid Phosphoramidate Monoesters via H-Phosphonate Intermediates

  1. Cindy J. Choy,
  2. Dan P. Drontle,
  3. Carston R. Wagner

Published Online: 1 JUL 2006

DOI: 10.1002/0471142700.nc1501s25

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Choy, C. J., Drontle, D. P. and Wagner, C. R. 2006. Synthesis of Amino Acid Phosphoramidate Monoesters via H-Phosphonate Intermediates. Current Protocols in Nucleic Acid Chemistry. 25:15.1:15.1.1–15.1.12.

Author Information

  1. University of Minnesota, Minneapolis, Minnesota

Publication History

  1. Published Online: 1 JUL 2006
  2. Published Print: JUN 2006

Abstract

Diphenyl phosphite and bis(N,N-diisopropylamino)chlorophosphine are used as phosphitylating reagents to generate H-phosphonate monoesters. These H-phosphonate intermediates are subsequently oxidized with iodine to generate the 5′-nucleoside amino acid phosphoramidates.

Keywords:

  • diphenyl phosphite;
  • bis(N,N-diisopropylamino)chlorophosphine;
  • phosphoramidate;
  • AZT;
  • nucleoside monophosphate;
  • oxidation