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Studies on the synthesis of proteinase inhibitors part 1 synthesis and activity of nona peptide fragments of soybean bowman birk inhibitor



Studies on the synthesis of proteinase inhibitors part 1 synthesis and activity of nona peptide fragments of soybean bowman birk inhibitor



Journal of Biochemistry (Tokyo) 82(3): 901-910



Two heterodetic cyclic nonapeptides, .**GRAPHIC**. (Ia: X = Ac, Y = NH2; Ib: X = H, Y = OH), which correspond to residues 14-22 in the sequence of Bowman-Birk inhibitor, were synthesized by Merrifield's solid-phase method. Inhibitory activites of Ia and Ib on tryptic hydrolysis of amide and ester substrates were examined. When Gly2-Lys-Gly3 and Tos-Arg-OMe were used as substrates, the values of I50 [50% inhibition] for the peptide Ia were calculated to be 3.6 .mu.M and 40 .mu.M, respectively. When Gly2-Lys-Gly3 was used as a substrate, the value of Ki was calculated to be 1.5 .mu.M. Ia was hydrolyzed slowly by trypsin [EC 3.4.21.4], losing the inhibitory activity. When the Lys-Ser bond of Ia was cleaved with trypsin, the modified Ia could not be regenerated by trypsin. The linear peptide S,S'-dicarboxamidomethyl-Ia also was inactive and appeared to be a good substrate. Optical rotatory dispersion studies showed that the active fragments have characteristic conformations which were lost upon modification to inactive derivatives.

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Accession: 006522365

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