Conformational peculiarities of biologically active MIF analogues

Yu. E. Shapiro, V. Ya. Gorbatyuk, V. M. Kabanov, A. A. Mazurov, S. A. Andronati, B. A. Lobasyuk, N. Ya. Golovenko, M. G. Rokachinskaya

A. V. Bogatsky Physico-Chemical Institute, Academy of Sciences of the Ukrainian SSR, Odessa

Abstract: On the basis of the two-dimensional 1H NMR studies the conformation of melanocy-te inhibiting hormone (HCl·Pro-Leu-Gly-NH2, MIF) and its five analogues with p-sub-stituted phenylalanine has been determined. Structure-antidepressant activity relationship (examined by the Porsolt test) of MIF and its analogues has been estimated by means of the multivariety statistical analysis, the vicinal spin coupling constants, which determine φ and χ dihedral angles of the second amino acid and φ dihedral angle of glycine, being selected as structural parameters. It is shown that a biologically active conformation (10-membered β-turn II) is realized for the considered peptides.

Russian Journal of Bioorganic Chemistry 1990, 16 (12):1607-1617

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