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 catalysts of a model peptide ligation reaction between thioester 1b and thiol 2 to give the amide product 5.
Harwig
C W
CW
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.
Hoffman
T Z
TZ
Wentworth
A D
AD
Janda
K D
KD
D000911:Antibodies, Monoclonal / Q000737:chemistry*; D000918:Antibody Specificity; D001386:Azides / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis*; D006241:Haptens / Q000737:chemistry* / Q000276:immunology; D008025:Ligases / Q000096:biosynthesis*
D000911:Antibodies, Monoclonal; D001386:Azides; D004952:Esters; D006241:Haptens; D008025:Ligases