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l-Alanylglycylhistamine dihydro­chloride

In the title compound {systematic name: 4-[2-({N-[(2S)-2-ammonio­propano­yl]glyc­yl}amino)­eth­yl]-1H-imidazol-3-ium dichloride}, C(10)H(19)N(5)O(2) (2+)·2Cl(−), the pseudo-tripeptide l-alanyl­glycyl­histamine is protonated at both the terminal amino group and the histidine N2 atom. The resulting po...

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Detalles Bibliográficos
Autores principales: Selmeczi, Katalin, Gizzi, Patrick, Wenger, Emmanuel, Henry, Bernard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379473/
https://www.ncbi.nlm.nih.gov/pubmed/22719671
http://dx.doi.org/10.1107/S1600536812023562
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author Selmeczi, Katalin
Gizzi, Patrick
Wenger, Emmanuel
Henry, Bernard
author_facet Selmeczi, Katalin
Gizzi, Patrick
Wenger, Emmanuel
Henry, Bernard
author_sort Selmeczi, Katalin
collection PubMed
description In the title compound {systematic name: 4-[2-({N-[(2S)-2-ammonio­propano­yl]glyc­yl}amino)­eth­yl]-1H-imidazol-3-ium dichloride}, C(10)H(19)N(5)O(2) (2+)·2Cl(−), the pseudo-tripeptide l-alanyl­glycyl­histamine is protonated at both the terminal amino group and the histidine N2 atom. The resulting positive charges are neutralized by two chloride anions. In the crystal, the organic cation adopts a twisted conformation about the CH(2)—CH(2) bond of histamine and about the C—N bond in the main chain, stabilized by a short intra­molecular C—H⋯O contact. In the crystal, N(+)—H⋯O and N(+)—H⋯Cl(−) hydrogen bonds link the mol­ecules into infinite sheets parallel to the (100) plane. The stacking of these sheets along the a axis is supported by N(amide)—H⋯Cl(−) hydrogen bonds.
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spelling pubmed-33794732012-06-20 l-Alanylglycylhistamine dihydro­chloride Selmeczi, Katalin Gizzi, Patrick Wenger, Emmanuel Henry, Bernard Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound {systematic name: 4-[2-({N-[(2S)-2-ammonio­propano­yl]glyc­yl}amino)­eth­yl]-1H-imidazol-3-ium dichloride}, C(10)H(19)N(5)O(2) (2+)·2Cl(−), the pseudo-tripeptide l-alanyl­glycyl­histamine is protonated at both the terminal amino group and the histidine N2 atom. The resulting positive charges are neutralized by two chloride anions. In the crystal, the organic cation adopts a twisted conformation about the CH(2)—CH(2) bond of histamine and about the C—N bond in the main chain, stabilized by a short intra­molecular C—H⋯O contact. In the crystal, N(+)—H⋯O and N(+)—H⋯Cl(−) hydrogen bonds link the mol­ecules into infinite sheets parallel to the (100) plane. The stacking of these sheets along the a axis is supported by N(amide)—H⋯Cl(−) hydrogen bonds. International Union of Crystallography 2012-05-31 /pmc/articles/PMC3379473/ /pubmed/22719671 http://dx.doi.org/10.1107/S1600536812023562 Text en © Selmeczi 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
Selmeczi, Katalin
Gizzi, Patrick
Wenger, Emmanuel
Henry, Bernard
l-Alanylglycylhistamine dihydro­chloride
title l-Alanylglycylhistamine dihydro­chloride
title_full l-Alanylglycylhistamine dihydro­chloride
title_fullStr l-Alanylglycylhistamine dihydro­chloride
title_full_unstemmed l-Alanylglycylhistamine dihydro­chloride
title_short l-Alanylglycylhistamine dihydro­chloride
title_sort l-alanylglycylhistamine dihydro­chloride
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379473/
https://www.ncbi.nlm.nih.gov/pubmed/22719671
http://dx.doi.org/10.1107/S1600536812023562
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AT henrybernard lalanylglycylhistaminedihydrochloride