Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification

The pKa, the negative logarithm of the acid dissociation equilibrium constant, of the carboxylic acid groups of unconjugated bilirubin in water is a discussed issue because there are quite different experimental values reported. Using quantum mechanical calculations we have studied the conformationa...

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Autores principales: Vega Hissi, Esteban Gabriel, Estrada, Mario Rinaldo, Lavecchia, Martín José, Pis Diez, Reinaldo
Formato: Articulo
Lenguaje:Inglés
Publicado: 2013
Materias:
Pka
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/104345
http://hdl.handle.net/11336/4389
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id I19-R120-10915-104345
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Computational analysis
Unconjugated bilirrubin
Pka
spellingShingle Química
Computational analysis
Unconjugated bilirrubin
Pka
Vega Hissi, Esteban Gabriel
Estrada, Mario Rinaldo
Lavecchia, Martín José
Pis Diez, Reinaldo
Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification
topic_facet Química
Computational analysis
Unconjugated bilirrubin
Pka
description The pKa, the negative logarithm of the acid dissociation equilibrium constant, of the carboxylic acid groups of unconjugated bilirubin in water is a discussed issue because there are quite different experimental values reported. Using quantum mechanical calculations we have studied the conformational behavior of unconjugated bilirubin species (in gas phase and in solution modeled implicitly and explicitly) to provide evidence that may clarify pKa values because of its pathophysiological relevance. Our results show that rotation of carboxylate group, which is not restricted, settles it in a suitable place to establish stronger interactions that stabilizes the monoanion and the dianion to be properly solvated, demonstrating that the rationalization used to justify the high pKa values of unconjugated bilirubin is inappropriate. Furthermore, low unconjugated bilirubin (UCB) pKa values were estimated from a linear regression analysis.
format Articulo
Articulo
author Vega Hissi, Esteban Gabriel
Estrada, Mario Rinaldo
Lavecchia, Martín José
Pis Diez, Reinaldo
author_facet Vega Hissi, Esteban Gabriel
Estrada, Mario Rinaldo
Lavecchia, Martín José
Pis Diez, Reinaldo
author_sort Vega Hissi, Esteban Gabriel
title Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification
title_short Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification
title_full Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification
title_fullStr Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification
title_full_unstemmed Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification
title_sort computational chemical analysis of unconjugated bilirubin anions and insights into pka values clarification
publishDate 2013
url http://sedici.unlp.edu.ar/handle/10915/104345
http://hdl.handle.net/11336/4389
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