Artículo
A full conformational space analysis of bilirubin
Vega Hissi, Esteban Gabriel
; Garro Martinez, Juan Ceferino
; Zamarbide, Graciela Nidia; Estrada, Mario Rinaldo; Knak Jensen, Svend J.; Tomas Vert, Francisco; Csizmadia, Imre G.
Fecha de publicación:
10/2009
Editorial:
Elsevier Science
Revista:
Journal of Molecular Structure Theochem
ISSN:
0166-1280
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
Ab initio methods were utilized in a gas-phase systematic conformational search of bilirubin conformers. The whole molecule was divided into four fragments. Most stable conformers of them were employed to build 196 conformers of the complete bilirubin molecule. Initial geometries were optimized using HF/321Glevel of theory and the minimum energy conformerswere then reoptimized at B3LYP/6-31G(d) level. Ridge-tile conformer was the most stable one, in perfect agreement with X-ray data. We found that while tetrapyrrole backbone shows some flexibility, propionic acid side chains have a greater influence in bilirubin conformation because they can interact through different hydrogen bond patterns with the backbone and between them.
Palabras clave:
BILIRRUBIN
,
RIDGE-TILE
,
HYDROGEN BOND PATTERN
,
FLEXIBILITY
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Licencia
Identificadores
Colecciones
Articulos(CCT - SAN LUIS)
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - SAN LUIS
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - SAN LUIS
Citación
Vega Hissi, Esteban Gabriel; Garro Martinez, Juan Ceferino; Zamarbide, Graciela Nidia; Estrada, Mario Rinaldo; Knak Jensen, Svend J.; et al.; A full conformational space analysis of bilirubin; Elsevier Science; Journal of Molecular Structure Theochem; 911; 1-3; 10-2009; 24-29
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