Syntheses are described of two kallidin (Lys-bradykinin) analogues in which the phenylalanine residue in position 6 is replaced by either tyrosine or tryptophan. The linear kinins and the two decapeptides containing all residues constituting the Tyr(6)- and the Trp(6)-kallidin were prepared by the solid-phase procedure based on Fmoc chemistry. Cyclization was carried out by both the diphenylphosphorazide and the TBTU-HOBt procedure. Peptides were characterized by amino acid analysis, optical rotation, analytical HPLC and mass spectrometry. Consistently with previous findings, preliminary pharmacological experiments on rat duodenum preparations showed that cyclic analogues were significantly less potent than the linear ones.
Linear and cyclic Tyr(6)- and Trp(6)-kallidin (Lys-bradykinin) analogues
GOBBO, MARINA;BIONDI, LAURA;FILIRA, FERNANDO;ROCCHI, RANIERO;
1996
Abstract
Syntheses are described of two kallidin (Lys-bradykinin) analogues in which the phenylalanine residue in position 6 is replaced by either tyrosine or tryptophan. The linear kinins and the two decapeptides containing all residues constituting the Tyr(6)- and the Trp(6)-kallidin were prepared by the solid-phase procedure based on Fmoc chemistry. Cyclization was carried out by both the diphenylphosphorazide and the TBTU-HOBt procedure. Peptides were characterized by amino acid analysis, optical rotation, analytical HPLC and mass spectrometry. Consistently with previous findings, preliminary pharmacological experiments on rat duodenum preparations showed that cyclic analogues were significantly less potent than the linear ones.Pubblicazioni consigliate
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