Design and synthesis of an alpha,alpha-difluorophosphinate hapten for antibody-catalyzed hydrolysis of organophosphorus nerve agents.
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 alpha,alpha-difluorophosphinate hapten 6. Various methods for the introduction of the key alpha,alpha-difluoromethyl feature into the phosphinate hapten are discussed. The best results were obtained with the electrophilic gem-difluorinating agent N-fluorobenzenesulfonimide.
Vayron
P
P
CEA, Service des Molécules Marquées, Gif sur Yvette, France.
Renard
P Y
PY
Valleix
A
A
Mioskowski
C
C
D017151:Antibodies, Catalytic / Q000737:chemistry* / Q000276:immunology; D002619:Chemical Warfare Agents / Q000737:chemistry; D015195:Drug Design; D006241:Haptens / Q000737:chemistry* / Q000276:immunology; D008958:Models, Molecular; D018696:Neuroprotective Agents / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000737:chemistry; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000276:immunology
D017151:Antibodies, Catalytic; D002619:Chemical Warfare Agents; D006241:Haptens; D018696:Neuroprotective Agents; D009943:Organophosphorus Compounds; D010721:Phosphinic Acids