{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T20:53:37Z","timestamp":1761512017501,"version":"build-2065373602"},"reference-count":30,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2004,12,3]],"date-time":"2004-12-03T00:00:00Z","timestamp":1102032000000},"content-version":"vor","delay-in-days":2,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Mass Spectrom."],"published-print":{"date-parts":[[2004,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Glutathione and other intracellular low molecular mass thiols act both as the major endogenous antioxidant and redox buffer system and, as recently highlighted, as an important regulator of cellular homeostasis. Such cellular functions are mediated by protein thiolation, a newly recognized post\u2010translational modification which involves the formation of mixed disulfides between GSH and key disulfide\u2010linked Cys residues in the native protein structure. It is also well known that thiol\u2010seeking heavy metals, such as mercury, cadmium and lead, may interfere in this regulatory system, thus disrupting the cellular functioning. To identify such mixed disulfides in order to investigate their biological role, 15 homo\u2010 and heterodimeric disulfides were prepared by air oxidation of binary mixtures containing cysteine, homocysteine, penicillamine, <jats:italic>N<\/jats:italic>\u2010acetylcysteine, <jats:italic>N<\/jats:italic>\u2010acetylpenicillamine and glutathione and their protonated molecules were characterized by mass spectrometry. Collisionally activated unimolecular decomposition of protonated homo\u2010 and heterodimeric disulfides generated by electrospray ionization gives rise to fission of the disulfide system both between the two sulfur atoms and across the C\uf8ffS bonds, to yield structurally specific fragments which allow one to define the structure of the compounds and to discriminate between isomeric compounds. Fission between the sulfur atoms yields a pair of R\uf8ffS<jats:sup>+<\/jats:sup> ions and, in some cases, also the complementary fragments corresponding to the protonated amino acids. Fission across the C\uf8ffS bonds mainly occurs in the disulfides of <jats:italic>N<\/jats:italic>\u2010acetylcysteine and <jats:italic>N<\/jats:italic>\u2010acetylpenicillamine and gives rise to non\u2010S\u2010containing fragments formally similar to those obtained from some mercapturic acids. The complementary fragments, formally connected as R\uf8ffS\uf8ffS<jats:sup>+<\/jats:sup> ions are also observed. Fragmentation of glutathione disulfides mainly shows the characteristic loss of the terminal \u03b3\u2010linked glutamic acid and little, if any, fragmentation of the disulfide system. Copyright \u00a9 2004 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/jms.745","type":"journal-article","created":{"date-parts":[[2004,12,3]],"date-time":"2004-12-03T06:47:41Z","timestamp":1102056461000},"page":"1408-1416","source":"Crossref","is-referenced-by-count":24,"title":["Characterization of the disulfides of bio\u2010thiols by electrospray ionization and triple\u2010quadrupole tandem mass spectrometry"],"prefix":"10.1002","volume":"39","author":[{"given":"Federico Maria","family":"Rubino","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cinzia","family":"Verduci","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rosario","family":"Giampiccolo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Salvatore","family":"Pulvirenti","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gabri","family":"Brambilla","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Antonio","family":"Colombi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2004,12,3]]},"reference":[{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-2952(02)01172-3"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-2952(02)01176-0"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-2952(02)01173-5"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-2952(02)01560-5"},{"key":"e_1_2_5_6_2","doi-asserted-by":"crossref","first-page":"1049","DOI":"10.1016\/S0006-2952(02)01175-9","article-title":"Glutathionylation of proteins by glutathione disulfide S\u2010oxide","volume":"64","author":"Kuo\u2010Ping H","year":"2002","journal-title":"Biochem. 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