New Insights into the Cystine-Sulfite Reaction

The mechanism by which cysteine-S-sulfate is formed from the reaction of sulfite with cystine in the absence of a dedicated oxidizing agent is investigated using high-resolution NMR. Changes to reactant ratio, pH, UV light exposure and temperature were evaluated to determine the most effective condi...

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Autores principales: Zecchini, Matteo, Lucas, Robert, Le Gresley, Adam
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6650951/
https://www.ncbi.nlm.nih.gov/pubmed/31252546
http://dx.doi.org/10.3390/molecules24132377
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author Zecchini, Matteo
Lucas, Robert
Le Gresley, Adam
author_facet Zecchini, Matteo
Lucas, Robert
Le Gresley, Adam
author_sort Zecchini, Matteo
collection PubMed
description The mechanism by which cysteine-S-sulfate is formed from the reaction of sulfite with cystine in the absence of a dedicated oxidizing agent is investigated using high-resolution NMR. Changes to reactant ratio, pH, UV light exposure and temperature were evaluated to determine the most effective conditions to achieve the maximum yield of cysteine-S-sulfate without recourse to conventional oxidizing reagents. Herein evidence is provided for both nucleophilic and radical mechanisms, by which cysteine-S-sulfate can be generated with yields of up to 96%.
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spelling pubmed-66509512019-08-07 New Insights into the Cystine-Sulfite Reaction Zecchini, Matteo Lucas, Robert Le Gresley, Adam Molecules Article The mechanism by which cysteine-S-sulfate is formed from the reaction of sulfite with cystine in the absence of a dedicated oxidizing agent is investigated using high-resolution NMR. Changes to reactant ratio, pH, UV light exposure and temperature were evaluated to determine the most effective conditions to achieve the maximum yield of cysteine-S-sulfate without recourse to conventional oxidizing reagents. Herein evidence is provided for both nucleophilic and radical mechanisms, by which cysteine-S-sulfate can be generated with yields of up to 96%. MDPI 2019-06-27 /pmc/articles/PMC6650951/ /pubmed/31252546 http://dx.doi.org/10.3390/molecules24132377 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zecchini, Matteo
Lucas, Robert
Le Gresley, Adam
New Insights into the Cystine-Sulfite Reaction
title New Insights into the Cystine-Sulfite Reaction
title_full New Insights into the Cystine-Sulfite Reaction
title_fullStr New Insights into the Cystine-Sulfite Reaction
title_full_unstemmed New Insights into the Cystine-Sulfite Reaction
title_short New Insights into the Cystine-Sulfite Reaction
title_sort new insights into the cystine-sulfite reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6650951/
https://www.ncbi.nlm.nih.gov/pubmed/31252546
http://dx.doi.org/10.3390/molecules24132377
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