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In nature, further modifications of the \u03b1,\u03b2\u2010dehydroamino acids were found, for example, replacement of the C\u2010terminal amide group by oxazole ring. The conformational properties of oxazole\u2010dehydrophenylalanine residue (\u0394Phe\u2010Ozl), both isomers <jats:italic>Z<\/jats:italic> and <jats:italic>E<\/jats:italic>, were investigated. To determine all possible conformations, theoretical calculations were performed using Ac\u2010(Z\/E)\u2010\u0394Phe\u2010Ozl(4\u2010Me) model compounds at M06\u20102X\/6\u201031++G(d,p) level of theory. Ac\u2010(Z\/E)\u2010\u0394Phe\u2010Ozl\u20104\u2010COOEt compounds were synthesized and the conformational preferences of each isomer, Z and E, were investigated using FTIR and NMR\u2010NOE in solutions of increasing polarity (CHCl<jats:sub>3<\/jats:sub>, DMSO\u2010d6). The solid\u2010state low\u2010temperature structures of Ac\u2010(Z)\u2010\u0394Phe\u2010Ozl\u20104\u2010COOEt and its intermediate analog Ac\u2010(Z)\u2010\u0394Phe\u2010Ozn(4\u2010OH)\u20104\u2010COOEt were also determined. In a weakly polar environment, the \u0394Phe\u2010Ozl residue has a tendency to adopt the conformation \u03b22 with the calculated <jats:italic>\u03c6<\/jats:italic> and <jats:italic>\u03c8<\/jats:italic> angles of \u2212127\u00b0 and 0\u00b0 for the isomer Z and \u2212170\u00b0 and 26\u00b0 for the isomer E. The increase of environment polarity favors the helical conformation \u03b1 and the beta\u2010turn like conformation \u03b2, but the conformation \u03b22 seems to be still accessible. The (E)\u2010\u0394Phe\u2010Ozl residue can be obtained from the isomer Z in photoisomerization reaction. However, hydroxyl\u2010oxazoline\u2010dehydrophenylalanine \u0394Phe\u2010Ozn(4\u2010OH) decomposes in such conditions. Alternatively, (E)\u2010\u0394Phe\u2010NH<jats:sub>2<\/jats:sub> can be applied as a substrate in the Hantzsch reaction. \u00a9 2016 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 283\u2013294, 2016.<\/jats:p>","DOI":"10.1002\/bip.22852","type":"journal-article","created":{"date-parts":[[2016,4,10]],"date-time":"2016-04-10T17:42:25Z","timestamp":1460310145000},"page":"283-294","source":"Crossref","is-referenced-by-count":6,"title":["Conformational preferences and synthesis of isomers <i>Z<\/i> and <i>E<\/i> of oxazole\u2010dehydrophenylalanine"],"prefix":"10.1002","volume":"106","author":[{"given":"Monika","family":"Sta\u015b","sequence":"first","affiliation":[{"name":"Faculty of Chemistry University of Opole Oleska 48 Opole 45\u2010052 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maciej","family":"Bujak","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry University of Opole Oleska 48 Opole 45\u2010052 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ma\u0142gorzata A.","family":"Broda","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry University of 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