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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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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. |
format | Online Article Text |
id | pubmed-3379473 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT selmeczikatalin lalanylglycylhistaminedihydrochloride AT gizzipatrick lalanylglycylhistaminedihydrochloride AT wengeremmanuel lalanylglycylhistaminedihydrochloride AT henrybernard lalanylglycylhistaminedihydrochloride |