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

ABSTRACT: 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.

SUBMITTER: Bartoccini F

PROVIDER: S-EPMC9361291 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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

Bartoccini Francesca F Retini Michele M Crinelli Rita R Menotta Michele M Fraternale Alessandra A Piersanti Giovanni G

The Journal of organic chemistry 20220721 15

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 p<i>K</i><sub>a</sub> value of 8.0, NACMEAA is reactive and user-friendly. We also demonstrate that NACMEAA reduces disul ...[more]

PMID: 35862282

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