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The synthesized compounds, especially <jats:bold>1<\/jats:bold>\u2010Pro\u2010His, remarkably promoted <jats:italic>S<\/jats:italic>\u2010denitrosylation of nitrosothiols (RSNO) via a catalytic cycle involving the reversible redox reaction between the diselenide and its corresponding diselenol ([SeH,SeH]) form with coexisting reductant thiols (R\u2032SH), during which the [SeH,SeH] form as a key reactive species reduces RSNO to the corresponding thiol (RSH). Structural analyses of <jats:bold>1<\/jats:bold>\u2010Pro\u2010His suggested that the peptide backbone of [SeH,SeH] is rigidly bent to form a \u03b3\u2010turn, possibly including an NH\u22c5\u22c5\u22c5Se hydrogen bond between the imidazole ring of His and selenol group, thus stabilizing the [SeH,SeH] form thermodynamically, and dramatically enhancing the catalytic activity. Furthermore, the synthetic compounds were found to prohibit <jats:italic>S<\/jats:italic>\u2010nitrosylation\u2010induced protein misfolding in the presence of RSNO, eventually implying their potential as a drug seed for misfolding diseases caused by the dysregulation of the <jats:italic>S<\/jats:italic>\u2010denitrosylation system.<\/jats:p>","DOI":"10.1002\/cbic.202100394","type":"journal-article","created":{"date-parts":[[2021,8,4]],"date-time":"2021-08-04T22:02:24Z","timestamp":1628114544000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["<i>S<\/i>\u2010Denitrosylase\u2010Like Activity of Cyclic Diselenides Conjugated with Xaa\u2010His Dipeptide: Role of Proline Spacer as a Key Activity Booster"],"prefix":"10.1002","volume":"23","author":[{"given":"Rumi","family":"Mikami","sequence":"first","affiliation":[{"name":"Department of Chemistry School of Science Tokai University  Kitakaname Hiratsuka-shi Kanagawa 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