{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,16]],"date-time":"2026-01-16T02:31:08Z","timestamp":1768530668840,"version":"3.49.0"},"reference-count":43,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2023,5,13]],"date-time":"2023-05-13T00:00:00Z","timestamp":1683936000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Protein Science"],"published-print":{"date-parts":[[2023,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>(2<jats:italic>R<\/jats:italic>)\u20104\u2010thiaproline (Thp) is an analog of proline, replacing C<jats:sup>\u03b3<\/jats:sup> in the pyrrolidine ring with sulfur. Its thiazolidine ring easily interconverts between <jats:italic>endo<\/jats:italic> and <jats:italic>exo<\/jats:italic> puckers due to a small energy barrier, which leads to destabilize polyproline helices. Collagen, composed of three polyproline II helices, mainly consists of X\u2013Y\u2013Gly triplets, where X is often proline and Y is frequently (2<jats:italic>S<\/jats:italic>,4<jats:italic>R<\/jats:italic>)\u2010hydroxyproline. In this study, we incorporated Thp into either position\u2010X or position\u2010Y to investigate the consequences of such a replacement on the triple helix. Circular dichroism and differential scanning calorimetry analyses showed that the Thp\u2010containing collagen\u2010mimetic peptides (CMPs) can fold into stable triple helices, in which the substitution at position\u2010Y exhibits a larger destabilization effect. Additionally, we also prepared the derivative peptides by oxidizing Thp in the peptide to <jats:italic>N<\/jats:italic>\u2010formyl\u2010cysteine or S,S\u2010dioxide Thp. The results showed that the oxidized derivatives at position\u2010X only slightly affect collagen stability, but those at position\u2010Y induce a large destabilization effect. The consequences of incorporating Thp and its oxidized derivatives into CMPs are position dependent. Computational results suggested that the ease of interconversion between <jats:italic>exo<\/jats:italic> and <jats:italic>endo<\/jats:italic> puckers for Thp and the twist conformation of S,S\u2010dioxide Thp may cause the destabilization effect at position\u2010Y. We have revealed new insights into the impacts of Thp and its oxidized derivatives on collagen and demonstrated that Thp can be used to design collagen\u2010related biomaterials.<\/jats:p>","DOI":"10.1002\/pro.4650","type":"journal-article","created":{"date-parts":[[2023,5,3]],"date-time":"2023-05-03T11:51:56Z","timestamp":1683114716000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Consequences of incorporating thiaproline and its oxidized derivatives into collagen triple helices"],"prefix":"10.1002","volume":"32","author":[{"given":"Tsai\u2010Ling","family":"Hsu","sequence":"first","affiliation":[{"name":"Department of Chemistry National Tsing Hua University  Hsinchu Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9936-5338","authenticated-orcid":false,"given":"Jia\u2010Cherng","family":"Horng","sequence":"additional","affiliation":[{"name":"Department of 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