Cyclolinopeptide K butanol disolvate monohydrate

• Main Authors: Pramodkumar Jadhav, Gabriele Schatte, Shaunivan Labiuk, Peta-Gaye Burnett, Bonnie Li, Denis Okinyo-Owiti, Martin Reaney, Pawel Grochulski, Michel Fodje, Ramaswami Sammynaiken
• Format: Article
• Language: English
• Published: International Union of Crystallography 2011-09-01
• Series: Acta Crystallographica Section E
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S1600536811032363

The title compound, C56H83N9O11S·2C4H10O·H2O, is a butanol–water solvate of the cyclolinopeptide cyclo(Metsulfone1-Leu2–Ile3–Pro4–Pro5–Phe6–Phe7–Val8–Ile9) (henceforth referred to as CLP-K) which was isolated from flax oil. All the amino acid residues are in an l configuration based on the CORN rule. The cyclic nonapeptide exhibits eight trans peptide bonds and one cis peptide bond observed between the two proline residues. The conformation is stabilized by an α- and a β-turn, each containing an N—H...O hydrogen bond between the carbonyl group O atom of the first residue and the amide group H atom of the fourth (α-turn) and the third residue (β-turn), repectively. In the crystal, the components of the structure are linked by intermolecular N—H...O and O—H...O hydrogen bonds into a two-dimensional network parallel to (001). The –C(H2)OH group of one of the butanol solvent molecules is disordered over two sets of sites with refined occupancies of 0.863 (4) and 0.137 (4).