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Journal Article

Unusual intramolecular hydrogen bonding in cycloamanide A, cyclic (LPro‐LVal‐LPhe‐LPhe‐LAla‐Gly)


Wieland,  Theodor
Max Planck Institute for Medical Research, Max Planck Society;

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Chiang, C. C., Karle, I. L., & Wieland, T. (1982). Unusual intramolecular hydrogen bonding in cycloamanide A, cyclic (LPro‐LVal‐LPhe‐LPhe‐LAla‐Gly). International journal of peptide and protein research, 20(5), 414-420. doi:10.1111/j.1399-3011.1982.tb03061.x.

Cite as: http://hdl.handle.net/21.11116/0000-0003-6FC4-4
The naturally occurring cyclic hexapeptide, cycloamanide A, has only one intramolecular hydrogen bond. It is a 4 leads to 1 type that encompasses the L Phe-L Ala sequence in which the experimentally determined phi, psi values are +54 degrees, -118 degrees and -88 degrees, -4 degrees, respectively. Even though the chirality is L, L, the phi, psi values are characteristic for a D, L beta-bend, Type II'. The conformation of the molecule was established by a crystal structure determination using X-ray diffraction analysis. Cycloamanide A (C33H42N6O6 . 4H2O) crystallizes in space group P2(1)2(1)2(1) with cell parameters a = 13.307(2) A, b = 24.820(4)A and c = 11.231(1)A.