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Conformational properties of <jats:italic>N\u2010t<\/jats:italic>\u2010butoxycarbonyl\u2010glycine\u2010(<jats:italic>E\/Z<\/jats:italic>)\u2010dehydrophenylalanine <jats:italic>N\u2032,N<\/jats:italic>\u2032\u2010dimethylamides (Boc\u2010Gly\u2010(<jats:italic>E\/Z<\/jats:italic>)\u2010\u0394Phe\u2010NMe<jats:sub>2<\/jats:sub>) in chloroform were studied by NMR and IR spectroscopy. The experimental findings were supported by extensive calculations at DFT(B3LYP, M06\u20102X) and MP2 levels of theory and the \u03b2\u2010turn tendency for both isomers of the studied dipeptide were determined in vacuum and in solution. The theoretical data and experimental IR results were used as an additional information for the NMR\u2010based determination of the detailed solution conformations of the peptides. The obtained results reveal that N\u2010methylation of C\u2010terminal amide group changes dramatically the conformational properties of studied dehydropeptides. Theoretical conformational analysis reveals that the tendency to adopt \u03b2\u2010turn conformations is much weaker for the <jats:italic>N<\/jats:italic>\u2010methylated <jats:italic>Z<\/jats:italic> isomer (Boc\u2010Gly\u2010(<jats:italic>Z<\/jats:italic>)\u2010\u0394Phe\u2010NMe<jats:sub>2<\/jats:sub>), both in vacuum and in polar environment. On the contrary, <jats:italic>N<\/jats:italic>\u2010methylated <jats:italic>E<\/jats:italic> isomer (Boc\u2010Gly\u2010(<jats:italic>E<\/jats:italic>)\u2010\u0394Phe\u2010NMe<jats:sub>2<\/jats:sub>) can easily adopt \u03b2\u2010turn conformation, but the backbone torsion angles (<jats:italic>\u03c6<\/jats:italic><jats:sub>1<\/jats:sub>, <jats:italic>\u03c8<\/jats:italic><jats:sub>1<\/jats:sub>, <jats:italic>\u03c6<\/jats:italic><jats:sub>2<\/jats:sub>, <jats:italic>\u03c8<\/jats:italic><jats:sub>2<\/jats:sub>) are off the limits for common \u03b2\u2010turn types. \u00a9 2013 Wiley Periodicals, Inc. Biopolymers 101: 28\u201340, 2014.<\/jats:p>","DOI":"10.1002\/bip.22264","type":"journal-article","created":{"date-parts":[[2013,4,20]],"date-time":"2013-04-20T08:34:55Z","timestamp":1366446895000},"page":"28-40","source":"Crossref","is-referenced-by-count":23,"title":["Toward engineering efficient peptidomimetics. 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