Synthesis and biological properties of a cyclic analog of ACTH-(5-14)-decapeptide

A cyclic analogue and the corresponding linear segment of the corticotropin molecule, namely ACTH-(5-14)- and [cyclo (Glu gamma-epsilon Lys)]ACTH-(5-14)-decapeptide, both including the specific and unspecific active centers of the ACTH molecule, have been synthesized and studied. The cyclic structur...

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Bibliographic Details
Published inBioorganicheskaia khimiia Vol. 10; no. 10; p. 1326
Main Authors Liepkaula, I K, Skuin'sh, A A, Romanovskiĭ, P Ia, Porunkevich, E A, Ratkevich, M P
Format Journal Article
LanguageRussian
Published Russia (Federation) 01.10.1984
Subjects
Adrenal Cortex - metabolism
Adrenal Cortex Hormones - biosynthesis
Adrenocorticotropic Hormone - chemical synthesis
Adrenocorticotropic Hormone - pharmacology
Animals
Anura
Cyclization
In Vitro Techniques
Melanins - biosynthesis
Melanocytes - metabolism
Peptide Fragments - chemical synthesis
Peptide Fragments - pharmacology
Rats
Skin - metabolism
Structure-Activity Relationship
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Summary:A cyclic analogue and the corresponding linear segment of the corticotropin molecule, namely ACTH-(5-14)- and [cyclo (Glu gamma-epsilon Lys)]ACTH-(5-14)-decapeptide, both including the specific and unspecific active centers of the ACTH molecule, have been synthesized and studied. The cyclic structure is fixed by amide bond between the glutamic acid and lysine side chains. Condensation of fragments has been realized by azide or DCC/HOBT methods. Cyclization has been achieved using diphenylphosphorylazide. The cyclic analogue has full steroidogenic activity, while its melanotropic activity is 3 orders of magnitude higher than that of the linear decapeptide.
ISSN:0132-3423