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We systematically investigated the intrinsic conformational propensities of dipeptides of bridged bicyclic \u03b2\u2010amino acids by means of accelerated molecular dynamics simulation and density functional theory (DFT) calculations in methanol, chloroform, and water. While the main\u2010chain conformation, represented by <jats:italic>\u03c6<\/jats:italic> and <jats:italic>\u03b8<\/jats:italic> values, is fixed by the nature of the bicyclic ring structure, rotation of the C\u2010terminal carbonyl group (<jats:italic>\u03c8<\/jats:italic>) is also restricted, converging to one or two minima. In <jats:italic>endo<\/jats:italic>\u2010type dipeptides, in which the two N\u2010 and C\u2010terminal amides are spatially close to each other, the C\u2010terminal amide plane is placed horizontally. In <jats:italic>exo<\/jats:italic>\u2010type dipeptides, in which the two amides are on opposite sides of the ring plane, the C\u2010terminal carbonyl group can take two types of positions: either parallel\/antiparallel with the N\u2010terminal carbonyl or beneath the bicyclic ring, forcing the amide NHMe moiety to lie outside of the ring. We also examined the <jats:italic>cis\u2010trans<\/jats:italic> preference of model bicyclic amides. Although the parent amides exhibit <jats:italic>cis\u2010trans<\/jats:italic> equilibrium without any preference, addition of a methyl group on one of the bridgehead positions tips the equilibrium towards <jats:italic>trans.<\/jats:italic><\/jats:p>","DOI":"10.1002\/chir.23220","type":"journal-article","created":{"date-parts":[[2020,4,2]],"date-time":"2020-04-02T03:29:15Z","timestamp":1585798155000},"page":"790-807","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Conformational preference of bicyclic \u03b2\u2010amino acid dipeptides"],"prefix":"10.1002","volume":"32","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8104-283X","authenticated-orcid":false,"given":"Yuko","family":"Otani","sequence":"first","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences The University of Tokyo  Tokyo 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