Syntheses are described of the endo-Lys(8a)-vespulakinin 1 and of cyclo-Thr(6)- and cyclo-N-epsilon-Lys-bradykinin. The linear peptides covering the entire sequences of endo-Lys(8a)-VSK-1 and Thr(6)-BK, and the decapeptide containing all residues constituting Lys-BK, with a Arg-Lys peptide bond involving the epsilon-amino function of lysine, were prepared by the solid-phase procedure based on Fmoc chemistry. Cyclization was carried out by the diphenylphosphorazide method. The amino-terminal octapeptide sequence of vespulakinin 1, Fmoc-Thr(tBu)-Ala-Thr(tBu)-Thr(tBu)-Arg(Pmc)-Arg(Pmc)-Arg(Pmc)-Gly-OH, and its N-alpha-Boc-[(Gal beta)Thr(3), (Gal beta)Thr(4)]-analogue, were used to prepare N-alpha-(1-8 VSK 1)-cyclo-N-epsilon-kallidin and N-alpha-[(Gal beta)Thr(3), (Gal beta)Thr(4), 1-8 VSK 1]-cyclo-N-epsilon-kallidin. Peptides and glycopeptides were characterized by amino-acid analysis, optical rotation, analytical HPLC and FAB-MS. Consistent with previous findings, preliminary pharmacological experiments on smooth muscle preparations showed that the cyclic, or partially cyclic, analogues were significatively less potent than the linear ones. (C) Munksgaard 1995.

Cyclic Analogs of Thr(6)-bradykinin, N-epsilon-Lys-bradykinin and Endo-Lys(8a)-vespulakinin-1

GOBBO, MARINA;BIONDI, LAURA;FILIRA, FERNANDO;ROCCHI, RANIERO
1995

Abstract

Syntheses are described of the endo-Lys(8a)-vespulakinin 1 and of cyclo-Thr(6)- and cyclo-N-epsilon-Lys-bradykinin. The linear peptides covering the entire sequences of endo-Lys(8a)-VSK-1 and Thr(6)-BK, and the decapeptide containing all residues constituting Lys-BK, with a Arg-Lys peptide bond involving the epsilon-amino function of lysine, were prepared by the solid-phase procedure based on Fmoc chemistry. Cyclization was carried out by the diphenylphosphorazide method. The amino-terminal octapeptide sequence of vespulakinin 1, Fmoc-Thr(tBu)-Ala-Thr(tBu)-Thr(tBu)-Arg(Pmc)-Arg(Pmc)-Arg(Pmc)-Gly-OH, and its N-alpha-Boc-[(Gal beta)Thr(3), (Gal beta)Thr(4)]-analogue, were used to prepare N-alpha-(1-8 VSK 1)-cyclo-N-epsilon-kallidin and N-alpha-[(Gal beta)Thr(3), (Gal beta)Thr(4), 1-8 VSK 1]-cyclo-N-epsilon-kallidin. Peptides and glycopeptides were characterized by amino-acid analysis, optical rotation, analytical HPLC and FAB-MS. Consistent with previous findings, preliminary pharmacological experiments on smooth muscle preparations showed that the cyclic, or partially cyclic, analogues were significatively less potent than the linear ones. (C) Munksgaard 1995.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11577/2510880
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