title: [Synthesis of [cyclo(Glu gamma-----epsilon Lys(Gly)]ACTH-(5-14) undecapeptide. Biological and physico-chemical properties of analogs of ACTH-(5-10)- and ACTH-(5-14)-peptides].
abstract: Modified corticotropin fragment - [Lys11 (Gly)]ACTH-(5-14)- and its cyclic analogue - [cyclo (Glu gamma----epsilon Lys (Gly)] ACTH-(5-14)-undecapeptides have been synthesized by classical approach. The cyclic structure has been fixed by amide bond between gamma-COOH group of glutamic acid and alpha-NH2 group of glycine coupled to the epsilon-NH2 group of lysine. Fragment condensation has been achieved by azide or dicyclohexylcarbodiimide methods. Cyclization has been performed using diphenylphosphorylazide. The melanotropic activity of the cyclicanalogue on isolated frog skin exceeds by two orders of magnitude that of the linear undecapeptide, however the steroidogenic activity in isolated cells of rat adrenal cortex is diminished by an order of magnitude as compared with that of the linear precursor. A similarity of the CD spectra for the cyclic ACTH peptides and their linear counterparts in water and trifluoroethanol points to the similarity and relative rigidity of their structures.
mesh_terms: D000305:Adrenal Cortex Hormones / Q000096:biosynthesis; D000311:Adrenal Glands / Q000187:drug effects / Q000378:metabolism; D000324:Adrenocorticotropic Hormone / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D002942:Circular Dichroism; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008544:Melanocytes / Q000187:drug effects / Q000378:metabolism; D010446:Peptide Fragments / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D011898:Ranidae; D051381:Rats; D012880:Skin Pigmentation / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000305:Adrenal Cortex Hormones; D010446:Peptide Fragments; D010456:Peptides, Cyclic; C043875:ACTH (5-14); C035065:ACTH (5-10); D000324:Adrenocorticotropic Hormone
vernacular_title: Sintez [tsiklo(Glu gamma----epsilon Lys(Gly)]-ACTH-(5-14) undekapeptida. Biologicheskie i fiziko-khimicheskie svoĭstva analogov ACTH-(5-10)- i ACTH-(5-14)-peptidov.