T. V. Berestova, L. A. Khamitova, O. V. Lusina, L. G. Kuzina, A. N. Lobov, A. G. Mustafin, “NMR study of thiosulfate-assisted oxidation of L-cysteine”, Mendeleev Commun., 2023, Volume 33, Issue 1,Pages <nobr>99

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Communications

NMR study of thiosulfate-assisted oxidation of L-cysteine

T. V. Berestova^a, L. A. Khamitova^a, O. V. Lusina^a, L. G. Kuzina^a, A. N. Lobov^b, A. G. Mustafin^ab

^a Department of Chemistry, Bashkir State University, Ufa, Russian Federation
^b Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

Abstract: The reaction of L-cysteine with sodium thiosulfate in aqueous solution at pH 9 affords mainly L-cystine with noticeable amounts of L-cysteine sulfonic anion ^–O₂CCH(NH⁺)CH SO^–. NMR study revealed the formation of intermediate L-cysteine sulfenic acid and L-cysteine S-sulfite, the latter existing in two active forms ^–O₂CCH(NH₂)CH₂S(=S)O^– and ^–O CCH(NH)CH SSO^–.

Keywords: oxidation, L-cysteine, L-cystine, thiosulfate, L-cysteine S-sulfite, L-cysteine sulfenic acid, thiols, disulfides, NMR study.

Language: English

DOI: 10.1016/j.mencom.2023.01.031

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