Synthesis and study of cyclic and linear analogs of neurotensin

New cyclic analogues of neurotensin (NT): [cyclo (13---8), Gly8]NT-(8-13), [cyclo (13---7), Gly7]NT-(7-13), [cyclo (13---5 epsilon), Lys5]NT-(5-13), [cyclo (13---4 epsilon), Lys4]NT-(4-13), and their linear precursors have been synthesized. The latter (protected linear compounds) were prepared by so...

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Bibliographic Details
Published inBioorganicheskaia khimiia Vol. 11; no. 12; p. 1589
Main Authors Grinshteĭne, I V, Myshliakova, N V, Vegner, R E, Vosekalna, I A, Gaĭlite, E A
Format Journal Article
LanguageRussian
Published Russia (Federation) 01.12.1985
Subjects
Amino Acid Sequence
Animals
Blood Pressure - drug effects
Chromatography, High Pressure Liquid
Circular Dichroism
Guinea Pigs
Ileum - drug effects
In Vitro Techniques
Male
Muscle Contraction - drug effects
Muscle, Smooth - drug effects
Neurotensin - analogs & derivatives
Neurotensin - chemical synthesis
Neurotensin - pharmacology
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - pharmacology
Protein Conformation
Rats
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Summary:New cyclic analogues of neurotensin (NT): [cyclo (13---8), Gly8]NT-(8-13), [cyclo (13---7), Gly7]NT-(7-13), [cyclo (13---5 epsilon), Lys5]NT-(5-13), [cyclo (13---4 epsilon), Lys4]NT-(4-13), and their linear precursors have been synthesized. The latter (protected linear compounds) were prepared by solid-phase peptide synthesis, and cyclization was attained by using diphenylphosphoryl azide. Cyclization of C-terminal hexa- and octapeptide fragments of NT was found to lead to cycloanalogues possessing high depressor activity. As judged by CD spectral data in aqueous solution, the cyclohexapeptide analogue has a relatively rigid conformation different from its linear counter-part and the NT-(9-13) fragment, whereas NT, its cyclohepta- and cyclononapeptides have random structure.
ISSN:0132-3423