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Cyclo­linopeptide B methanol tris­olvate

The title compound, C(56)H(83)N(9)O(9)S·3CH(3)OH, is a methanol tris­olvate of the cyclo­linopeptide cyclo(Met(1)—Leu(2)—Ile(3)—Pro(4)—Pro(5)—Phe(6)—Phe(7)—Val(8)—Ile(9)) (henceforth referred to as CLP-B), which was isolated from flaxseed oil. All the amino acid residues are in an l-configuration ba...

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Autores principales: Schatte, Gabriele, Labiuk, Shaunivan, Li, Bonnie, Burnett, Peta-Gaye, Reaney, Martin, Grochulski, Pawel, Fodje, Michel, Yang, Jian, Sammynaiken, Ramaswami
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254409/
https://www.ncbi.nlm.nih.gov/pubmed/22259553
http://dx.doi.org/10.1107/S1600536811051488
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author Schatte, Gabriele
Labiuk, Shaunivan
Li, Bonnie
Burnett, Peta-Gaye
Reaney, Martin
Grochulski, Pawel
Fodje, Michel
Yang, Jian
Sammynaiken, Ramaswami
author_facet Schatte, Gabriele
Labiuk, Shaunivan
Li, Bonnie
Burnett, Peta-Gaye
Reaney, Martin
Grochulski, Pawel
Fodje, Michel
Yang, Jian
Sammynaiken, Ramaswami
author_sort Schatte, Gabriele
collection PubMed
description The title compound, C(56)H(83)N(9)O(9)S·3CH(3)OH, is a methanol tris­olvate of the cyclo­linopeptide cyclo(Met(1)—Leu(2)—Ile(3)—Pro(4)—Pro(5)—Phe(6)—Phe(7)—Val(8)—Ile(9)) (henceforth referred to as CLP-B), which was isolated from flaxseed 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-turn and two consecutive β-turns each containing a 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) or the third residue (β-turns), repectively. In the crystal, the components of the structure are linked by N—H⋯O and O—H⋯O hydrogen bonds into chains parallel to the a axis.
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spelling pubmed-32544092012-01-18 Cyclo­linopeptide B methanol tris­olvate Schatte, Gabriele Labiuk, Shaunivan Li, Bonnie Burnett, Peta-Gaye Reaney, Martin Grochulski, Pawel Fodje, Michel Yang, Jian Sammynaiken, Ramaswami Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(56)H(83)N(9)O(9)S·3CH(3)OH, is a methanol tris­olvate of the cyclo­linopeptide cyclo(Met(1)—Leu(2)—Ile(3)—Pro(4)—Pro(5)—Phe(6)—Phe(7)—Val(8)—Ile(9)) (henceforth referred to as CLP-B), which was isolated from flaxseed 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-turn and two consecutive β-turns each containing a 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) or the third residue (β-turns), repectively. In the crystal, the components of the structure are linked by N—H⋯O and O—H⋯O hydrogen bonds into chains parallel to the a axis. International Union of Crystallography 2011-12-07 /pmc/articles/PMC3254409/ /pubmed/22259553 http://dx.doi.org/10.1107/S1600536811051488 Text en © Schatte et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Schatte, Gabriele
Labiuk, Shaunivan
Li, Bonnie
Burnett, Peta-Gaye
Reaney, Martin
Grochulski, Pawel
Fodje, Michel
Yang, Jian
Sammynaiken, Ramaswami
Cyclo­linopeptide B methanol tris­olvate
title Cyclo­linopeptide B methanol tris­olvate
title_full Cyclo­linopeptide B methanol tris­olvate
title_fullStr Cyclo­linopeptide B methanol tris­olvate
title_full_unstemmed Cyclo­linopeptide B methanol tris­olvate
title_short Cyclo­linopeptide B methanol tris­olvate
title_sort cyclo­linopeptide b methanol tris­olvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254409/
https://www.ncbi.nlm.nih.gov/pubmed/22259553
http://dx.doi.org/10.1107/S1600536811051488
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