Hydrolysis of organophosphorus nerve agent soman by the monoclonal antibodies elicited against an oxyphosphorane hapten

• Published in: Acta chemica Scandinavica (Copenhagen. 1989) Vol. 53; no. 7; pp. 473 - 479
• Main Authors: Yli-Kauhaluoma, J, Humppi, T, Yliniemela, A
• Format: Journal Article
• Language: English
• Published: COPENHAGEN Wiley 01.07.1999
• Subjects: Animals; Antibodies, Monoclonal - metabolism; Biochemistry & Molecular Biology; Chemical Warfare Agents - chemistry; Chemical Warfare Agents - metabolism; Chemistry; Chemistry, Multidisciplinary; Cholinesterase Inhibitors - chemistry; Cholinesterase Inhibitors - immunology; Cholinesterase Inhibitors - metabolism; Haptens - chemistry; Hydrolysis; Kinetics; Life Sciences & Biomedicine; Mice; Models, Molecular; Physical Sciences; Science & Technology; Soman - chemistry; Soman - immunology; Soman - metabolism; CATALYTIC ANTIBODIES; PHOSPHORUS; DIVERSITY; IMMUNOASSAY
• ISSN: 0904-213X
• DOI: 10.3891/acta.chem.scand.53-0473

The antibody-mediated hydrolysis of the nerve agent O-1,2,2-trimethylpropyl methylphosphonofluoridate (soman) 1 has now been established with two monoclonal antibodies raised against the cyclic pentacovalent methyloxyphosphorane hapten 10 that mimics the pentacoordinated trigonal bipyramidal transition-state of the reaction. The hydrolysis reaction was studied using molecular orbital methods at the MP2/6-31 + G*//HF/6-31 + G* level of accuracy. According to the nb initio carculations, the reaction seems to proceed via three separate transition-states. The calculations are in good agreement with the experimental results. The 1,3-dioxabenzophosphole hapten 10 was synthesized, coupled to the carrier protein and the antibodies were obtained by the hybridoma technique. Two antibodies, DB-108P and DB-108Q were found to enhance the rate of soman hydrolysis and they were kinetically characterised.