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dc.contributor.author
Lara Popoca, Jesús  
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Thoke, Henrik S.  
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Stock, Roberto P.  
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Rudino Pinera, Enrique  
dc.contributor.author
Bagatolli, Luis Alberto  
dc.date.available
2021-09-13T16:15:15Z  
dc.date.issued
2020-12  
dc.identifier.citation
Lara Popoca, Jesús; Thoke, Henrik S.; Stock, Roberto P.; Rudino Pinera, Enrique; Bagatolli, Luis Alberto; Inductive effects in amino acids and peptides: Ionization constants and tryptophan fluorescence; Elsevier; Biochemistry and Biophysics Reports; 24; 12-2020; 1-9  
dc.identifier.issn
2405-5808  
dc.identifier.uri
http://hdl.handle.net/11336/140204  
dc.description.abstract
Although inductive effects in organic compounds are known to influence chemical properties such as ionization constants, their specific contribution to the properties/behavior of amino acids and functional groups in peptides remains largely unexplored. In this study we developed a computationally economical algorithm for ab initio calculation of the magnitude of inductive effects for non-aromatic molecules. The value obtained by the algorithm is called the Inductive Index and we observed a high correlation (R2 = 0.9427) between our calculations and the pKa values of the alpha-amino groups of amino acids with non-aromatic side-chains. Using a series of modified amino acids, we also found similarly high correlations (R2 > 0.9600) between Inductive Indexes and two wholly independent chemical properties: i) the pKa values of ionizable side-chains and, ii) the fluorescence response of the indole group of tryptophan. After assessing the applicability of the method of calculation at the amino acid level, we extended our study to tryptophan-containing peptides and established that inductive contributions of neighboring side-chains are transmitted through peptide bonds. We discuss possible contributions to the study of proteins.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Elsevier  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by/2.5/ar/  
dc.subject
AMINO ACIDS  
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COMPUTATIONAL MODEL  
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INDUCTIVE EFFECTS  
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IONIZATION CONSTANTS  
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PEPTIDES  
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TRYPTOPHAN FLUORESCENCE  
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Biofísica  
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Ciencias Biológicas  
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CIENCIAS NATURALES Y EXACTAS  
dc.title
Inductive effects in amino acids and peptides: Ionization constants and tryptophan fluorescence  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2021-08-25T19:27:55Z  
dc.journal.volume
24  
dc.journal.pagination
1-9  
dc.journal.pais
Países Bajos  
dc.journal.ciudad
Amsterdam  
dc.description.fil
Fil: Lara Popoca, Jesús. Universidad Nacional Autónoma de México; México  
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Fil: Thoke, Henrik S.. International and Interdisciplinary Research Network; Dinamarca  
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Fil: Stock, Roberto P.. Universidad Nacional Autónoma de México; México  
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Fil: Rudino Pinera, Enrique. Universidad Nacional Autónoma de México; México  
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Fil: Bagatolli, Luis Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación Médica Mercedes y Martín Ferreyra. Universidad Nacional de Córdoba. Instituto de Investigación Médica Mercedes y Martín Ferreyra; Argentina  
dc.journal.title
Biochemistry and Biophysics Reports  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.bbrep.2020.100802