{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T09:56:13Z","timestamp":1791194173437,"version":"4.1.0"},"reference-count":79,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2010,11,19]],"date-time":"2010-11-19T00:00:00Z","timestamp":1290124800000},"content-version":"vor","delay-in-days":322,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biopolymers"],"published-print":{"date-parts":[[2010,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The design of folded structures in peptides containing the higher homologues of \u03b1\u2010amino acid residues requires the restriction of the range of local conformational choices. In \u03b1\u2010amino acids stereochemically constrained residues like \u03b1,\u03b1\u2010dialkylated residue, aminoisobutyric acid (Aib), and <jats:sc>D<\/jats:sc>\u2010Proline (<jats:sup>D<\/jats:sup>Pro) have proved extremely useful in the design of helices and hairpins in short peptides. Extending this approach, backbone substitution and cyclization are anticipated to be useful in generating conformationally constrained \u03b2\u2010 and \u03b3\u2010residues. This brief review provides a survey of work on hybrid peptide sequences concerning the conformationally constrained \u03b3\u2010amino acid residue 1\u2010aminomethyl cyclohexane acetic acid, gabapentin (Gpn). This achiral, \u03b2,\u03b2\u2010disubstituted, \u03b3\u2010residue strongly favors <jats:italic>gauche\u2010gauche<\/jats:italic> conformations about the C<jats:sup>\u03b1<\/jats:sup>\u2010C<jats:sup>\u03b2<\/jats:sup> (\u03b8<jats:sub>2<\/jats:sub>) and C<jats:sup>\u03b2<\/jats:sup>\u2010C<jats:sup>\u03b3<\/jats:sup> (\u03b8<jats:sub>1<\/jats:sub>) bonds, facilitating local folding. The Gpn residue can adopt both C<jats:sub>7<\/jats:sub> (NH<jats:sub>i<\/jats:sub>\u2192CO<jats:sub>i<\/jats:sub>) and C<jats:sub>9<\/jats:sub> (CO<jats:sub>i\u20101<\/jats:sub>\u2190NH<jats:sub>i+1<\/jats:sub>) hydrogen bonds which are analogous to the C<jats:sub>5<\/jats:sub> and C<jats:sub>7<\/jats:sub> (\u03b3\u2010turn) conformations at \u03b1\u2010residues. In conjunction with adjacent residues, Gpn may be used in \u03b1\u03b3 and \u03b3\u03b1 segments to generate C<jats:sub>12<\/jats:sub> hydrogen bonded conformations which may be considered as expanded analogs of conventional \u03b2\u2010turns. The structural characterization of C<jats:sub>12<\/jats:sub> helices, C<jats:sub>12<\/jats:sub>\/C<jats:sub>10<\/jats:sub> helices with mixed hydrogen bond directionalities and \u03b2\u2010hairpins incorporating Gpn residues at the turn segment is illustrated. \u00a9 2010 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 94: 733\u2013741, 2010.<\/jats:p><jats:p>This article was originally published online as an accepted preprint. The \u201cPublished Online\u201d date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at <jats:ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"biopolymers@wiley.com\">biopolymers@wiley.com<\/jats:ext-link><\/jats:p>","DOI":"10.1002\/bip.21468","type":"journal-article","created":{"date-parts":[[2010,8,5]],"date-time":"2010-08-05T18:23:40Z","timestamp":1281032620000},"page":"733-741","source":"Crossref","is-referenced-by-count":16,"title":["Hybrid polypeptides: Gabapentin as a stereochemically constrained \u03b3\u2010amino acid residue"],"prefix":"10.1002","volume":"94","author":[{"given":"Padmanabhan","family":"Balaram","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,11,19]]},"reference":[{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.bi.11.070142.000331"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60102a002"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.37.4.205"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.37.11.729"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja991185g"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja990748l"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF02708230"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.39.6.470"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/0968-0004(91)90142-I"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461127"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-3233(08)60402-7"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1py00061f"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-3233(08)60520-3"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1098\/rspa.1950.0142"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1038\/311053a0"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.200490087"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar700263g"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1098\/rsif.2006.0203"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/a704933a"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar960298r"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar800009n"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr000045i"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.1995199507163"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19950780516"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja970566w"},{"key":"e_1_2_5_27_2","first-page":"1067","volume":"73","author":"Banerjee A.","year":"1997","journal-title":"Curr Sci"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-3495(65)86759-5"},{"key":"e_1_2_5_29_2","first-page":"851","volume":"59","author":"Ramakrishnan C.","year":"1990","journal-title":"Curr Sci"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/prot.340070107"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi035522g"},{"key":"e_1_2_5_32_2","series-title":"Progress in Peptide Research","first-page":"195","author":"Ramachandran G. 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