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Acta Cryst. (2002). E58, o62-o64  [ doi:10.1107/S1600536801021079 ]

The cis,cis-proline isomer of ceratospongamide

M. Doi, A. Yumiba and A. Asano

Abstract: Ceratospongamide, cyclo(-Ile-Oxz-Phe-Pro-Thz-Phe-Pro-) (Oxz = oxazoline and Thz = thiazole), C41H49N7O6S, is a thiazole-containing cyclic peptide isolated from marine sources. Two stable isomers are known and the structure of the cis,cis-isomer has been determined. The peptide ring is folded in a new manner for thiazole-containing peptides. The thiazole ring faces the amide bond plane between the Oxz and Phe residues, with [pi]-[pi] interactions. This interaction stabilizes the peptide conformation with no hydrogen bonding.

Online 14 December 2001


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