Journal of the Chemical Society. Perkin transactions II p. 1743 - 1748 (1988)
Update date:2022-08-02
Topics:
Ozeki, Eiichi
Kimura, Shunsaku
Imanishi, Yukio
The cyclic dodecapeptide, cyclo(L-Leu-L-Phe-L-Pro)4, was synthesized, and its conformation and complexation with metal ions in acetonitrile were investigated by c.d. and n.m.r. spectroscopy.Cyclo(L-Leu-L-Phe-L-Pro)4 was found to complex selectively with alkaline earth metal ions.The binding constant of the dodecapeptide with Ba2+ was larger than that of the cyclic hexapeptide, cyclo(L-Leu-L-Phe-L-Pro)2.In the free state, the skeletal conformation of the cyclic dodecapeptide ic non-symmetrical.When complexed with Ba2+, the conformation changes to a C4-symmetrical one having all peptide bonds in a trans configuration and four β-turn structures containing transannular hydrogen bonds.Formation of hydrogen bonds on complexation with the cation accounts for the large binding constant of the cyclic dodecapeptide.
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