Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent

[Image: see text] We report the synthesis, chemical properties, and disulfide bond-reducing performance of a dithiol called NACMEAA, conceived as a hybrid of two biologically relevant thiols: cysteine and cysteamine. NACMEAA is conveniently prepared from inexpensive l-cystine in an efficient manner....

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Autores principales: Bartoccini, Francesca, Retini, Michele, Crinelli, Rita, Menotta, Michele, Fraternale, Alessandra, Piersanti, Giovanni
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361291/
https://www.ncbi.nlm.nih.gov/pubmed/35862282
http://dx.doi.org/10.1021/acs.joc.2c01050
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author Bartoccini, Francesca
Retini, Michele
Crinelli, Rita
Menotta, Michele
Fraternale, Alessandra
Piersanti, Giovanni
author_facet Bartoccini, Francesca
Retini, Michele
Crinelli, Rita
Menotta, Michele
Fraternale, Alessandra
Piersanti, Giovanni
author_sort Bartoccini, Francesca
collection PubMed
description [Image: see text] We report the synthesis, chemical properties, and disulfide bond-reducing performance of a dithiol called NACMEAA, conceived as a hybrid of two biologically relevant thiols: cysteine and cysteamine. NACMEAA is conveniently prepared from inexpensive l-cystine in an efficient manner. As a nonvolatile, highly soluble, and neutral compound at physiological pH with the first thiol pK(a) value of 8.0, NACMEAA is reactive and user-friendly. We also demonstrate that NACMEAA reduces disulfide bonds in GSSG and lysozyme.
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spelling pubmed-93612912022-08-10 Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent Bartoccini, Francesca Retini, Michele Crinelli, Rita Menotta, Michele Fraternale, Alessandra Piersanti, Giovanni J Org Chem [Image: see text] We report the synthesis, chemical properties, and disulfide bond-reducing performance of a dithiol called NACMEAA, conceived as a hybrid of two biologically relevant thiols: cysteine and cysteamine. NACMEAA is conveniently prepared from inexpensive l-cystine in an efficient manner. As a nonvolatile, highly soluble, and neutral compound at physiological pH with the first thiol pK(a) value of 8.0, NACMEAA is reactive and user-friendly. We also demonstrate that NACMEAA reduces disulfide bonds in GSSG and lysozyme. American Chemical Society 2022-07-21 2022-08-05 /pmc/articles/PMC9361291/ /pubmed/35862282 http://dx.doi.org/10.1021/acs.joc.2c01050 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Bartoccini, Francesca
Retini, Michele
Crinelli, Rita
Menotta, Michele
Fraternale, Alessandra
Piersanti, Giovanni
Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent
title Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent
title_full Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent
title_fullStr Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent
title_full_unstemmed Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent
title_short Dithiol Based on l-Cysteine and Cysteamine as a Disulfide-Reducing Agent
title_sort dithiol based on l-cysteine and cysteamine as a disulfide-reducing agent
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361291/
https://www.ncbi.nlm.nih.gov/pubmed/35862282
http://dx.doi.org/10.1021/acs.joc.2c01050
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