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

CW Harwig, TZ Hoffman, AD Wentworth…

Index: Harwig, Curtis W.; Hoffman, Timothy Z.; Wentworth, Anita D.; Janda, Kim D. Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 9 p. 915 - 918

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Citation Number: 6

Abstract

A four-step, one-pot synthesis of mixed α-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.