Inhibitors of polyamine biosynthesis VI: 2,5-Diamino-2-(cyanomethyl) pentanoic acid, a potential irreversible inhibitor of ornithine decarboxylase.
(+/-)-2,5-Diamino-2-)cyanomethyl)pentanoic acid was obtained by the reaction of chloracetonitrile with the anion obtained by treatment of 3-(benzylideneamino)-2-piperidinone with sodium hydride, followed by hydrolysis in the presence of trifluoroacetic anhydride. The target compound was isolated as the monohydrochloride salt of the lactam. The compound was synthesized as a potential irreversible inhibitor of the enzyme L-ornithine decarboxylase by the mechanism generally known as suicide or Kcat inhibition. The synthesized compound produced no inhibition of the enzyme ornithine decarboxylase obtained from rat prostate gland. The inactivity of the target compound is attributed to the hydrophilicity of the cyanomethyl group.
D000599:Amino Acids, Diamino / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002262:Carboxy-Lyases / Q000037:antagonists & inhibitors*; D066298:In Vitro Techniques; D008297:Male; D008722:Methods; D009570:Nitriles / Q000138:chemical synthesis / Q000494:pharmacology; D065108:Ornithine Decarboxylase Inhibitors; D011467:Prostate / Q000201:enzymology; D051381:Rats; D013329:Structure-Activity Relationship
D000599:Amino Acids, Diamino; D009570:Nitriles; D065108:Ornithine Decarboxylase Inhibitors; D002262:Carboxy-Lyases