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The structural analysis was used to investigate the <jats:italic>cis\u2010trans<\/jats:italic> isomerization of the <jats:italic>N<\/jats:italic>\u2010terminal tertiary amide group of diamides: Ac\u2010(<jats:italic>Z<\/jats:italic>)\u2010\u0394(Me)Abu\u2010NHMe (<jats:bold>1<\/jats:bold>), Ac\u2010(<jats:italic>Z<\/jats:italic>)\u2010\u0394(Me)Phe\u2010NHMe (<jats:bold>2<\/jats:bold>), Ac\u2010(<jats:italic>E<\/jats:italic>)\u2010\u0394(Me)Phe\u2010NHMe (<jats:bold>3<\/jats:bold>), Ac\u2010\u0394(Me)Ala\u2010NHMe (<jats:bold>4<\/jats:bold>), and Ac\u2010(Me)Ala\u2010NHMe (<jats:bold>5<\/jats:bold>). The compounds were analyzed in the solid state by an X\u2010ray crystallography (<jats:bold>1<\/jats:bold>\u2013<jats:bold>3<\/jats:bold>), and in the solution by FTIR (MeCN and CHCl<jats:sub>3<\/jats:sub>) and NMR (DMSO\u2010d6 and CDCl<jats:sub>3<\/jats:sub>) methods (<jats:bold>1<\/jats:bold>\u2013<jats:bold>5<\/jats:bold>). In the solid state, the studied compounds adopt the <jats:italic>cis<\/jats:italic> configuration of <jats:italic>N<\/jats:italic>\u2010terminal amide. In solution, this configuration also prevails for the dehydroamino acids <jats:bold>1<\/jats:bold>\u2013<jats:bold>4<\/jats:bold>, in contrast to the saturated analog <jats:bold>5<\/jats:bold>. The results indicate that <jats:italic>N<\/jats:italic>\u2010methyldehydroamino acids present a promising tool to induce the <jats:italic>cis<\/jats:italic> configuration of the amide bond. \u00a9 2012 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 98: 466\u2013478, 2012.<\/jats:p>","DOI":"10.1002\/bip.22082","type":"journal-article","created":{"date-parts":[[2012,5,1]],"date-time":"2012-05-01T16:43:03Z","timestamp":1335890583000},"page":"466-478","source":"Crossref","is-referenced-by-count":13,"title":["The <i>cis\u2010trans<\/i> isomerization of <i>N<\/i>\u2010methyl\u2010\u03b1,\u03b2\u2010dehydroamino acids"],"prefix":"10.1002","volume":"98","author":[{"given":"Dawid","family":"Siod\u0142ak","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Agnieszka","family":"Macedowska\u2010Capiga","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ma\u0142gorzata A.","family":"Broda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna E.","family":"Kozio\u0142","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tadeusz","family":"Lis","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,9,14]]},"reference":[{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867023371049"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867043365224"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr040699h"},{"key":"e_1_2_5_5_2","first-page":"49","volume":"55","author":"Fulton N. 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