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Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate

In the title compound, phenyl (S)-2-[(S)-(1-{2-[(S)-(1-{[(tert-but­oxy)carbon­yl]amino}­bicyclo­[2.2.2]octan-2-yl)formamido]­propanamido}­bicyclo­[2.2.2]octan-2-yl)formamido]-3-phenyl­propano­ate chloro­form monosolvate, C(42)H(56)N(4)O(7)·CHCl(3), the α,β-hybrid peptide contains two non-proteinogen...

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Autores principales: Wenger, Emmanuel, Moulat, Laure, Legrand, Baptiste, Amblard, Muriel, Calmès, Monique, Didierjean, Claude
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647376/
https://www.ncbi.nlm.nih.gov/pubmed/26594404
http://dx.doi.org/10.1107/S2056989015016941
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author Wenger, Emmanuel
Moulat, Laure
Legrand, Baptiste
Amblard, Muriel
Calmès, Monique
Didierjean, Claude
author_facet Wenger, Emmanuel
Moulat, Laure
Legrand, Baptiste
Amblard, Muriel
Calmès, Monique
Didierjean, Claude
author_sort Wenger, Emmanuel
collection PubMed
description In the title compound, phenyl (S)-2-[(S)-(1-{2-[(S)-(1-{[(tert-but­oxy)carbon­yl]amino}­bicyclo­[2.2.2]octan-2-yl)formamido]­propanamido}­bicyclo­[2.2.2]octan-2-yl)formamido]-3-phenyl­propano­ate chloro­form monosolvate, C(42)H(56)N(4)O(7)·CHCl(3), the α,β-hybrid peptide contains two non-proteinogenic amino acid residues of (S)-1-amino­bicyclo­[2.2.2]octane-2-carb­oxy­lic acid [(S)-ABOC], two amino acid residues of (S)-2-amino­propanoic acid [(S)-Ala] and (S)-2-amino-3-phenyl­propanoic acid [(S)-Phe], and protecting groups of tert-but­oxy­carbonyl (Boc) and benzyl ester (OBn). The tetra­mer folds into a right-handed mixed 11/9 helix stabilized by intra­molecular i,i + 3 and i,i − 1 C=O⋯H—N hydrogen bonds. In the crystal, the oligomers are linked by N—H⋯O=C hydrogen bonds into chains along the a-axis direction. The chloro­form solvent mol­ecules are inter­calated between the folded chains via C—H⋯O=C inter­actions.
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spelling pubmed-46473762015-11-20 Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate Wenger, Emmanuel Moulat, Laure Legrand, Baptiste Amblard, Muriel Calmès, Monique Didierjean, Claude Acta Crystallogr E Crystallogr Commun Research Communications In the title compound, phenyl (S)-2-[(S)-(1-{2-[(S)-(1-{[(tert-but­oxy)carbon­yl]amino}­bicyclo­[2.2.2]octan-2-yl)formamido]­propanamido}­bicyclo­[2.2.2]octan-2-yl)formamido]-3-phenyl­propano­ate chloro­form monosolvate, C(42)H(56)N(4)O(7)·CHCl(3), the α,β-hybrid peptide contains two non-proteinogenic amino acid residues of (S)-1-amino­bicyclo­[2.2.2]octane-2-carb­oxy­lic acid [(S)-ABOC], two amino acid residues of (S)-2-amino­propanoic acid [(S)-Ala] and (S)-2-amino-3-phenyl­propanoic acid [(S)-Phe], and protecting groups of tert-but­oxy­carbonyl (Boc) and benzyl ester (OBn). The tetra­mer folds into a right-handed mixed 11/9 helix stabilized by intra­molecular i,i + 3 and i,i − 1 C=O⋯H—N hydrogen bonds. In the crystal, the oligomers are linked by N—H⋯O=C hydrogen bonds into chains along the a-axis direction. The chloro­form solvent mol­ecules are inter­calated between the folded chains via C—H⋯O=C inter­actions. International Union of Crystallography 2015-09-17 /pmc/articles/PMC4647376/ /pubmed/26594404 http://dx.doi.org/10.1107/S2056989015016941 Text en © Wenger et al. 2015 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 Research Communications
Wenger, Emmanuel
Moulat, Laure
Legrand, Baptiste
Amblard, Muriel
Calmès, Monique
Didierjean, Claude
Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate
title Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate
title_full Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate
title_fullStr Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate
title_full_unstemmed Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate
title_short Crystal structure of Boc-(S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloro­form monosolvate
title_sort crystal structure of boc-(s)-aboc-(s)-ala-(s)-aboc-(s)-phe-obn chloro­form monosolvate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647376/
https://www.ncbi.nlm.nih.gov/pubmed/26594404
http://dx.doi.org/10.1107/S2056989015016941
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