Cyclic analogs of des-Arg9-[Leu8bradykinin

Four cyclic derivatives of des-Arg9[Leu8]bradykinin have been obtained by classical methods of peptide chemistry. They are cyclo-(-X-Arg-Pro-Pro-Gly-Phe-Gly-Pro-Leu-), where X=Lys or none, and cyclo-(Y-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Leu-), where Y= Lys or Orn. Peptide bonds have been formed by the pent...

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Bibliographic Details
Published inBioorganicheskaia khimiia Vol. 15; no. 3; p. 325
Main Authors Mutule, I E, Mutulis, F K, Rozite, S Kh, Porunkevich, E A, Ratkevich, M P
Format Journal Article
LanguageRussian
Published Russia (Federation) 01.03.1989
Subjects
Amino Acid Sequence
Bradykinin - analogs & derivatives
Bradykinin - chemical synthesis
Bradykinin - pharmacology
Chromatography, Liquid
Histamine Release - drug effects
Molecular Sequence Data
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - pharmacology
Structure-Activity Relationship
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Summary:Four cyclic derivatives of des-Arg9[Leu8]bradykinin have been obtained by classical methods of peptide chemistry. They are cyclo-(-X-Arg-Pro-Pro-Gly-Phe-Gly-Pro-Leu-), where X=Lys or none, and cyclo-(Y-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Leu-), where Y= Lys or Orn. Peptide bonds have been formed by the pentafluorophenylester method, and cyclization has been carried out in a diluted dioxane solution with 40% yield. Subsequent cleavage of protecting groups was made by treatment with hydrogen fluoride. The products obtained were purified by droplet counter-current chromatography. These substances liberate histamine from the rat mast cells comparably to bradykinin and fail to produce myotripic and vascular effects.
ISSN:0132-3423