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

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...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2000-05, Vol.10 (9), p.915-918
Main Authors: Harwig, C W, Hoffman, T Z, Wentworth, A D, Janda, K D
Format: Article
Language:English
Subjects:
Antibodies, Monoclonal - chemistry
Antibody Specificity
Azides - chemical synthesis
Esters - chemical synthesis
Haptens - chemistry
Haptens - immunology
Ligases - biosynthesis
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Summary: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.
ISSN:0960-894X
DOI:10.1016/S0960-894X(00)00137-2