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Design and Synthesis of an α , α ‐Difluorophosphinate Hapten for Antibody‐Catalyzed Hydrolysis of Organophosphorus Nerve Agents
Author(s) -
Vayron Philippe,
Renard PierreYves,
Valleix Alain,
Mioskowski Charles
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000317)6:6<1050::aid-chem1050>3.0.co;2-5
Subject(s) - hapten , chemistry , stereochemistry , catalysis , medicinal chemistry , antibody , biochemistry , immunology , biology
In a new approach to the safe neutralization of organophosphorus chemical weapons, we designed a hapten to elicit catalytic antibodies with phosphatase activity. Here we report the synthesis of this α , α ‐difluorophosphinate hapten 6 . Various methods for the introduction of the key α , α ‐difluoromethyl feature into the phosphinate hapten are discussed. The best results were obtained with the electrophilic gem ‐difluorinating agent N ‐fluorobenzenesulfonimide.