{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T21:56:18Z","timestamp":1790546178445,"version":"4.1.0"},"reference-count":41,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T00:00:00Z","timestamp":1790467200000},"content-version":"vor","delay-in-days":26,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100004044","name":"Kansai University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004044","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>Collagen is formed with a repeating structure of proline (Pro)\u20104\u2010hydroxyproline\u2010(4\u2010Hyp)\u2010glycine (Gly). In chemical synthesis, when synthesizing collagen sequences, it is necessary to protect the 4\u2010Hyp side chain within them. Therefore, if (Pro\u2010Pro\u2010Gly)n could be synthesized followed by selective hydroxylation of proline residues using iron catalysts, improved synthetic efficiency could be expected. In this study, hydroxylation reactions were performed on Boc\u2010Pro\u2010OPac and Ac\u2010Pro\u2010OPac, where the N\u2010termnus of proline is protected by Boc and Ac groups, respectively, and on Boc\u2010Pro\u2010Pro\u2010OPac, a peptide containing multiple proline residues. Subsequent NMR structural analysis confirmed that hydroxyl groups were introduced at the 5\u2010position of proline in Boc\u2010Pro\u2010OPac and at the 5\u2010position of N\u2010terminal proline in Boc\u2010Pro\u2010Pro\u2010OPac. On the other hand, the reaction did not proceed for the proline at the C\u2010terminal end of Ac\u2010Pro\u2010OPac and Boc\u2010Pro\u2010Pro\u2010OPac. To investigate the reaction mechanism and whether the reaction proceeds, density functional theory (DFT) calculations were performed to clarify the optimal structure of the substrate and the charge distribution on each atom. The progress of this reaction is influenced by the electron density of the hydrogen atom at the 5\u2010position of proline, but it has been clarified that steric hindrance near the 5\u2010position of proline exerts a significant effect.<\/jats:p>","DOI":"10.1002\/cbdv.71755","type":"journal-article","created":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T20:19:17Z","timestamp":1790540357000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Selective Hydroxylation of Collagen Model Peptides by Metal Catalysis"],"prefix":"10.1002","volume":"23","author":[{"given":"Shun","family":"Oto","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, Materials and Bioengineering Kansai University  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akihiro","family":"Marutani","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Materials and Bioengineering Kansai University  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-4643-0304","authenticated-orcid":false,"given":"Yukio","family":"Hamamoto","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Materials and Bioengineering Kansai University  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arata","family":"Kawakami","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Materials and Bioengineering Kansai University  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3702-9969","authenticated-orcid":false,"given":"Yasushi","family":"Obora","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Materials and Bioengineering Kansai University  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1126-5277","authenticated-orcid":false,"given":"Yoshiaki","family":"Hirano","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Materials and Bioengineering Kansai University  Suita Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,27]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.3109\/10409231003627991"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/pr900039c"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1042\/BCJ20170726"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.matbio.2023.12.001"},{"key":"e_1_2_9_6_1","first-page":"699","volume-title":"Encyclopedia of Polymer Science and Engineering","author":"Piez K. 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