Amino-acids and peptides. Part 48. Synthesis of bradykinyl-chloromethane.
An analogue of the local tissue hormone bradykinin, in which the terminal carboxy group is replaced by a chloromethyl ketone function, has been synthesised. A protected octapeptide, synthesised by the picolyl ester "handle" procedure, was coupled to N delta, N omega-dibenzyloxycarbonyl-L-arginyl-choromethane; the product was deprotected by hydrogen fluoride, giving bradykinyl-chloromethane. The preservation of the reactive chloromethyl ketone group and the entire structure of the product was confirmed by fast atom bombardment mass spectrometry. On the rat uterus and guinea-pig ileum bradykinyl-chloromethane was a weak agonist showing no antagonism of responses to bradykinin.
D000590:Amino Acid Chloromethyl Ketones / Q000138:chemical synthesis*; D000818:Animals; D001920:Bradykinin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005260:Female; D006168:Guinea Pigs; D066298:In Vitro Techniques; D013058:Mass Spectrometry; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D051381:Rats; D014590:Uterine Contraction / Q000187:drug effects
D000590:Amino Acid Chloromethyl Ketones; C038604:bradykinin chloromethyl ketone; D001920:Bradykinin