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Alkylboronic acids accelerate affinity labeling of acetylcholinesterase with N,N-dimethyl-2-phenylaziridinium ion

Alkylboronic acids accelerate affinity labeling of acetylcholinesterase with N,N-dimethyl-2-phenylaziridinium ion. Palumaa, P.; Jarv, J. (Dep. Org. Chem., Tartu State Univ., Tartu 202400, USSR). Biochim. Biophys. Acta, 784(1), 35-9 (English) 1984. CODEN: BBACAQ. ISSN: 0006-3002. DOCUMENT TYPE: Journal CA Section: 7 (Enzymes) The kinetics of cobra venom acetylcholinesterase (I) alkylation with N,N-dimethyl-2-phenylaziridinium ion, the anionic site-directed affinity label, was investigated in the presence of alkylboronic acids, which are known as esteratic site-directed reversible inhibitors of I. The ternary complex of I, the aziridinium ion, and alkylboronic acid, were formed in this reaction. In the case of propylboronic acid, for which the complete kinetic anal. of the acceleration effect was carried out, an 85-fold increase in the rate of I alkylation was found. This acceleration effect was connected with the alkylation step, whereas the noncovalent binding of the aziridinium ion in the I active center was even hindered by the alkylboronic acid. The possible mechanism of this kinetic acceleration phenomenon was discussed with special ref. to the kinetic data for the spontaneous solvolysis reaction of the aziridinium ion in water and org. 4737-50-2 and 4426-47-5 are just another two chemicals used in this study. solvents. .