Solid phase synthesis methodology on a benzhydrylamine resin was used for the synthesis of three analogues of vasopressin with the non-coded amino acid, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), in the position 2 ([Tic2, Lys8]VP (I)) and in the position 3 ([Tic3, Lys8]VP (II)). The analogue containing only one Tic in place of both aromatic residues was also isolated (des-Tyr2-[Tic3, Lys8]VP (III)). The biological activities of all analogues were negligible.
Dedicated 10 the 1l1f!lIwry of Dr Karel BhiIUl.Solid phase methodology all bcnzhydryluminc resin was used for the synthesis of three analogues of vasopressin with non-ceded amino ucid.1 -uminocyclopropunc-l-carbcxylic acid, in position 9. Two analogues oflysine-vuscprcssin ([Lysll, Acc'[vusopressln (I) and Glyr[Lysll. Acc''[vnsopressin (11) and one analogue of arginine-vasopressin ([Arg N, Acc'[vasoprcssln (111) have been synthesized. The dubious value of tile biological activity of [LysN, D-AlalJlvusopressin was reevaluated and [Lys'', L-Alu'Jlvusoprcssin wus also synthesized and tested for the comparlscu. Differences in solution conformation of these two unulogucs were studied by 11-1 and DC NMR spectroscopy. Biological activities of all analogues were either significantly lowered or almost completely eliminated. Analogues 1-111 were found to be completely inactive in analgesia and the eNS activities tested (active and passive avoidance).During the years of structure-activity studies, the extent of attention devoted to different positions in the peptide chain of vasopressin varied. As far as the position 9 is concerned, even though some analogues modified in this position
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