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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
Descripción
Sumario: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.