Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine

1H and 13C NMR measurements were carried out to explore anticipated correlations between chemical shifts versus thiolate basicities and redox potentials of cysteamine, homocysteine, penicillamine, and their homodisulfides. All correlations were analyzed and statistically evaluated. The closest corre...

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Main Authors: Juliana Ferreira de Santana, Arash Mirzahosseini, Béla Noszál
Format: Article
Language:English
Published: Wiley 2022-01-01
Series:Journal of Spectroscopy
Online Access:http://dx.doi.org/10.1155/2022/9491360
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author Juliana Ferreira de Santana
Arash Mirzahosseini
Béla Noszál
author_facet Juliana Ferreira de Santana
Arash Mirzahosseini
Béla Noszál
author_sort Juliana Ferreira de Santana
collection DOAJ
description 1H and 13C NMR measurements were carried out to explore anticipated correlations between chemical shifts versus thiolate basicities and redox potentials of cysteamine, homocysteine, penicillamine, and their homodisulfides. All correlations were analyzed and statistically evaluated. The closest correlation was observed for the αCH nuclei concerning 1H and 13C NMR data. Since neither site-specific basicities nor site-specific redox potentials can be directly measured by any means in peptides and proteins containing several thiol and/or disulfide units, these data provide a simple method and predictive power to estimate the aforementioned site-specific physicochemical parameters for analogous sulfur-containing moieties in related biopolymers.
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institution Kabale University
issn 2314-4939
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publishDate 2022-01-01
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series Journal of Spectroscopy
spelling doaj-art-32f0308b2dc34381b0edfa1a20d4d02a2025-08-20T03:55:17ZengWileyJournal of Spectroscopy2314-49392022-01-01202210.1155/2022/9491360Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and PenicillamineJuliana Ferreira de Santana0Arash Mirzahosseini1Béla Noszál2Department of Pharmaceutical ChemistryDepartment of Pharmaceutical ChemistryDepartment of Pharmaceutical Chemistry1H and 13C NMR measurements were carried out to explore anticipated correlations between chemical shifts versus thiolate basicities and redox potentials of cysteamine, homocysteine, penicillamine, and their homodisulfides. All correlations were analyzed and statistically evaluated. The closest correlation was observed for the αCH nuclei concerning 1H and 13C NMR data. Since neither site-specific basicities nor site-specific redox potentials can be directly measured by any means in peptides and proteins containing several thiol and/or disulfide units, these data provide a simple method and predictive power to estimate the aforementioned site-specific physicochemical parameters for analogous sulfur-containing moieties in related biopolymers.http://dx.doi.org/10.1155/2022/9491360
spellingShingle Juliana Ferreira de Santana
Arash Mirzahosseini
Béla Noszál
Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine
Journal of Spectroscopy
title Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine
title_full Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine
title_fullStr Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine
title_full_unstemmed Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine
title_short Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine
title_sort correlation between the nmr chemical shifts and thiolate protonation constants of cysteamine homocysteine and penicillamine
url http://dx.doi.org/10.1155/2022/9491360
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AT belanoszal correlationbetweenthenmrchemicalshiftsandthiolateprotonationconstantsofcysteaminehomocysteineandpenicillamine