{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,20]],"date-time":"2026-03-20T18:16:04Z","timestamp":1774030564730,"version":"3.50.1"},"reference-count":134,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2022,5,31]],"date-time":"2022-05-31T00:00:00Z","timestamp":1653955200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Scientific Grant Agency of the Ministry of Education of Slovak Republic and of Slovak Academy of Sciences VEGA 2\/0019\/19"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>We studied the kinetics of the reaction of N-acetyl-l-cysteine (NAC or RSH) with cupric ions at an equimolar ratio of the reactants in aqueous acid solution (pH 1.4\u20132) using UV\/Vis absorption and circular dichroism (CD) spectroscopies. Cu2+ showed a strong catalytic effect on the 2,2\u2032-azino-bis(3-ethylbenzothiazoline-6-sulfonate) radical (ABTSr) consumption and autoxidation of NAC. Difference spectra revealed the formation of intermediates with absorption maxima at 233 and 302 nm (\u03b5302\/Cu &gt; 8 \u00d7 103 M\u22121 cm\u22121) and two positive Cotton effects centered at 284 and 302 nm. These intermediates accumulate during the first, O2-independent, phase of the NAC autoxidation. The autocatalytic production of another chiral intermediate, characterized by two positive Cotton effects at 280 and 333 nm and an intense negative one at 305 nm, was observed in the second reaction phase. The intermediates are rapidly oxidized by added ABTSr; otherwise, they are stable for hours in the reaction solution, undergoing a slow pH- and O2-dependent photosensitive decay. The kinetic and spectral data are consistent with proposed structures of the intermediates as disulfide-bridged dicopper(I) complexes of types cis-\/trans-CuI2(RS)2(RSSR) and CuI2(RSSR)2. The electronic transitions observed in the UV\/Vis and CD spectra are tentatively attributed to Cu(I) \u2192 disulfide charge transfer with an interaction of the transition dipole moments (exciton coupling). The catalytic activity of the intermediates as potential O2 activators via Cu(II) peroxo-complexes is discussed. A mechanism for autocatalytic oxidation of Cu(I)\u2013thiolates promoted by a growing electronically coupled \u2013[CuI2(RSSR)]n\u2013 polymer is suggested. The obtained results are in line with other reported observations regarding copper-catalyzed autoxidation of thiols and provide new insight into these complicated, not yet fully understood systems. The proposed hypotheses point to the importance of the Cu(I)\u2013disulfide interaction, which may have a profound impact on biological systems.<\/jats:p>","DOI":"10.3390\/ijms23116199","type":"journal-article","created":{"date-parts":[[2022,6,1]],"date-time":"2022-06-01T03:33:18Z","timestamp":1654054398000},"page":"6199","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Reaction of N-Acetylcysteine with Cu2+: Appearance of Intermediates with High Free Radical Scavenging Activity: Implications for Anti-\/Pro-Oxidant Properties of Thiols"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3751-7567","authenticated-orcid":false,"given":"Ivan","family":"Valent","sequence":"first","affiliation":[{"name":"Department of Physical and Theoretical Chemistry, Faculty of Natural Sciences, Comenius University, Mlynsk\u00e1 dolina, Ilkovi\u010dova 6, 842 15 Bratislava, Slovakia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lucie","family":"Bedn\u00e1rov\u00e1","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo n\u00e1m\u011bst\u00ed 542\/2, 160 00 Praha 6, Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Igor","family":"Schreiber","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering, Faculty of Chemical Engineering, University of Chemistry and Technology, Prague, Technick\u00e1 5, 166 28 Praha 6, Czech Republic"},{"name":"Global Change Research Institute, Czech Academy of Sciences, B\u011blidla 986\/4a, 603 00 Brno, Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Juraj","family":"Bujd\u00e1k","sequence":"additional","affiliation":[{"name":"Department of Physical and Theoretical Chemistry, Faculty of Natural Sciences, Comenius University, Mlynsk\u00e1 dolina, Ilkovi\u010dova 6, 842 15 Bratislava, Slovakia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8467-893X","authenticated-orcid":false,"given":"Katar\u00edna","family":"Valachov\u00e1","sequence":"additional","affiliation":[{"name":"Centre of Experimental Medicine of Slovak Academy of Sciences, D\u00fabravsk\u00e1 cesta 9, 841 04 Bratislava, Slovakia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ladislav","family":"\u0160olt\u00e9s","sequence":"additional","affiliation":[{"name":"Centre of Experimental Medicine of Slovak Academy of Sciences, D\u00fabravsk\u00e1 cesta 9, 841 04 Bratislava, Slovakia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,31]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"513","DOI":"10.2174\/1389557519666191119144100","article-title":"Medicinal thiols: Current status and new perspectives","volume":"20","author":"Pfaff","year":"2020","journal-title":"Mini-Rev. 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