A one-pot multistep approach to alpha-azido-phosphonate and phosphonothioate diesters: key intermediates in the synthesis of haptens for the generation of antibody ligases

Bioorg Med Chem Lett. 2000 May 1;10(9):915-8. doi: 10.1016/s0960-894x(00)00137-2.

Abstract

A four-step, one-pot synthesis of mixed alpha-azido-phosphonates and phosphonothioates 12a-d is described. This chemistry has provided a facile route to haptens 6a b and 7 that have been employed for the elicitation of antibody ligases. Five hapten-specific antibodies have been identified as modest catalysts of a model peptide ligation reaction between thioester 1b and thiol 2 to give the amide product 5.

Publication types

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

MeSH terms

  • Antibodies, Monoclonal / chemistry*
  • Antibody Specificity
  • Azides / chemical synthesis*
  • Esters / chemical synthesis*
  • Haptens / chemistry*
  • Haptens / immunology
  • Ligases / biosynthesis*

Substances

  • Antibodies, Monoclonal
  • Azides
  • Esters
  • Haptens
  • Ligases