{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,14]],"date-time":"2025-05-14T00:12:24Z","timestamp":1747181544978,"version":"3.40.5"},"reference-count":19,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2024,8,9]],"date-time":"2024-08-09T00:00:00Z","timestamp":1723161600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,8,9]],"date-time":"2024-08-09T00:00:00Z","timestamp":1723161600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2024,8,7]]},"published-print":{"date-parts":[[2024,9,1]]},"abstract":"<jats:p>The cyclic peptide <jats:italic>cyclo<\/jats:italic>(Val-Leu-Leu-D-Phe-Pro)<jats:sub>2<\/jats:sub> (peptide <jats:bold>1<\/jats:bold>) was specifically designed for structural chemistry investigations, drawing inspiration from Gramicidin S (GS). Previous studies have shown that Pro residues within <jats:bold>1<\/jats:bold> adopt a down-puckering conformation of the pyrrolidine ring. By incorporating fluoride-Pro with 4-<jats:italic>trans<\/jats:italic>\/<jats:italic>cis<\/jats:italic>-isomers into <jats:bold>1<\/jats:bold>, an up-puckering conformation was successfully induced. In the current investigation, introducing hydroxyprolines with 4-<jats:italic>trans<\/jats:italic>\/<jats:italic>cis<\/jats:italic>-isomer configurations (tHyp\/cHyp) into <jats:bold>1<\/jats:bold> gave <jats:italic>cyclo<\/jats:italic>(Val-Leu-Leu-D-Phe-tHyp)<jats:sub>2<\/jats:sub> methanol disolvate monohydrate, C<jats:sub>62<\/jats:sub>H<jats:sub>94<\/jats:sub>N<jats:sub>10<\/jats:sub>O<jats:sub>12<\/jats:sub>\u00b72CH<jats:sub>4<\/jats:sub>O\u00b7H<jats:sub>2<\/jats:sub>O (<jats:bold>4<\/jats:bold>), and <jats:italic>cyclo<\/jats:italic>(Val-Leu-Leu-D-Phe-cHyp)<jats:sub>2<\/jats:sub> monohydrate, C<jats:sub>62<\/jats:sub>H<jats:sub>94<\/jats:sub>N<jats:sub>10<\/jats:sub>O<jats:sub>12<\/jats:sub>\u00b7H<jats:sub>2<\/jats:sub>O (<jats:bold>5<\/jats:bold>), respectively. However, the puckering of <jats:bold>4<\/jats:bold> and <jats:bold>5<\/jats:bold> remained in the down conformation, regardless of the geometric position of the hydroxyl group. Although the backbone structure of <jats:bold>4<\/jats:bold> with <jats:italic>trans<\/jats:italic>-substitution was asymmetric, the asymmetric backbone of <jats:bold>5<\/jats:bold> with <jats:italic>cis<\/jats:italic>-substitution was unexpected. It is speculated that the anticipated influence of stress from the geometric positioning, which was expected to affect the puckering, may have been mitigated by interactions between the hydroxyl groups of hydroxyproline, the solvent molecules, and peptides.<\/jats:p>","DOI":"10.1107\/s2056989024007771","type":"journal-article","created":{"date-parts":[[2024,8,9]],"date-time":"2024-08-09T08:51:59Z","timestamp":1723193519000},"page":"942-946","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Puckering effects of 4-hydroxy-<scp>L<\/scp>-proline isomers on the conformation of ornithine-free Gramicidin S"],"prefix":"10.1107","volume":"80","author":[{"given":"Akiko","family":"Asano","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kanako","family":"Nakayama","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sakura","family":"Okada","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2561-8582","authenticated-orcid":true,"given":"Takuma","family":"Kato","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8952-828X","authenticated-orcid":true,"given":"Mitsunobu","family":"Doi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2024,8,9]]},"reference":[{"key":"jp2008_bb1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.2116\/xraystruct.35.1","volume":"35","author":"Asano","year":"2019","journal-title":"X-ray Struct. 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