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Nevertheless, they often suffer from a weak stability in polar solvents because they exhibit a mixed hydrogen-bond network resulting in a small macrodipole. In this work, stable and functionalizable 12/10-helices were developed by alternating a highly constrained beta(2, 3, 3)-trisubstituted bicyclic amino acid (S)-1-aminobicyclo[2.2.2]octane-2-carboxylic acid ((S)-ABOC) and an acyclic substituted beta-homologated proteinogenic amino acid (l-beta(3)-hAA). Based on NMR spectroscopic analysis, it was shown that such mixed beta-peptides display well-defined right-handed 12/10-helices in polar, apolar, and chaotropic solvents; that are, CD3OH, CDCl3, and [D-6]DMSO, respectively. The stability of the hydrogen bonds forming the C-10 and C-12 pseudocycles as well as the benefit provided by the use of the constrained bicyclic ABOC versus typical acyclic beta-amino acids sequences when designing 12/10-helix were investigated using NH/ND NMR exchange experiments and DFT calculations in various solvents. These studies showed that the beta(3)-hAA/(S)-ABOC helix displayed a more stable hydrogen-bond network through specific stabilization of the C-10 pseudocycles involving the bridgehead NH of the ABOC bicyclic scaffold.", "subjects" : [ { "otype" : "Classification", "mtid" : 10293, "link" : "/api/classification/10293", "label" : "Chemical sciences", "published" : true, "snippet" : true } ], "keywords" : [ { "otype" : "Keyword", "mtid" : 18997, "link" : "/api/keyword/18997", "label" : "helical structures", "published" : true, "oldId" : 18997, "snippet" : true }, { "otype" : "Keyword", "mtid" : 1045884, "link" : "/api/keyword/1045884", "label" : "PROTEIN MODELS", "published" : true, "oldId" : 1045884, "snippet" : true }, { "otype" : "Keyword", "mtid" : 1114664, "link" : "/api/keyword/1114664", "label" : "BETA-PEPTIDE", "published" : true, "oldId" : 1114664, "snippet" : true }, { "otype" : "Keyword", "mtid" : 1154928, "link" : "/api/keyword/1154928", "label" : "foldamer", "published" : true, "oldId" : 1154928, "snippet" : true }, { "otype" : "Keyword", "mtid" : 1402739, "link" : "/api/keyword/1402739", "label" : "bicyclic beta-amino acids", "published" : true, "oldId" : 1402739, "snippet" : true }, { "otype" : "Keyword", "mtid" : 1542386, "link" : "/api/keyword/1542386", "label" : "helical stabilization", "published" : true, "snippet" : true } ], "digital" : null, "printed" : null, "sourceYear" : 2019, "foreignEdition" : true, "foreignLanguage" : true, "fullPublication" : true, "conferencePublication" : false, "nationalOrigin" : false, "missingAuthor" : false, "oaType" : "NONE", "oaCheckDate" : "2024-03-06", "oaFree" : false, "citationCount" : 0, "citationCountUnpublished" : 0, "citationCountWoOther" : 0, "independentCitCountWoOther" : 0, "doiCitationCount" : 0, "wosCitationCount" : 0, "scopusCitationCount" : 0, "independentCitationCount" : 0, "unhandledCitationCount" : 0, "citingPubCount" : 0, "independentCitingPubCount" : 0, "unhandledCitingPubCount" : 0, "citedPubCount" : 10, "citedCount" : 10, "ratings" : [ { "otype" : "SjrRating", "mtid" : 10762601, "link" : "/api/sjrrating/10762601", "label" : "sjr:D1 (2018) Scopus - Chemistry (miscellaneous) CHEMISTRY-A EUROPEAN JOURNAL 0947-6539 1521-3765", "listPos" : 31, "rankValue" : 0.1, "type" : "journal", "ratingType" : { "otype" : "RatingType", "mtid" : 10002, "link" : "/api/ratingtype/10002", "label" : "sjr", "code" : "sjr", "published" : true, "snippet" : true }, "subject" : { "otype" : "ClassificationExternal", "mtid" : 1601, "link" : "/api/classificationexternal/1601", "label" : "Scopus - Chemistry (miscellaneous)", "published" : true, "oldId" : 1601, "snippet" : true }, "ranking" : "D1", "calculation" : "DIRECT", "published" : true, "snippet" : true } ], "ratingsForSort" : "D1", "hasCitationDuplums" : false, "userChangeableUntil" : "2019-01-07T09:19:02.923+0000", "directInstitutesForSort" : "", "ownerAuthorCount" : 16, "ownerInstituteCount" : 45, "directInstituteCount" : 0, "authorCount" : 10, "contributorCount" : 0, "hasQualityFactor" : true, "link" : "/api/publication/30378683", "label" : "Simon Matthieu et al. 12/10-Helix in Mixed beta-Peptides Alternating Bicyclic and Acyclic beta-Amino Acids: Probing the Relationship between Bicyclic Side Chain and Helix Stability. 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