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The roles of residues adjacent to a tyrosine\u2013proline residue pair on <jats:italic>cis<\/jats:italic>\u2013<jats:italic>trans<\/jats:italic> isomerism were examined. A short series of peptides XYPZ was synthesized and <jats:italic>cis<\/jats:italic>\u2013<jats:italic>trans<\/jats:italic> isomerism was analyzed. Based on these initial studies, a series of peptides XYPN, X = all 20 canonical amino acids, was synthesized and analyzed by NMR for <jats:italic>i<\/jats:italic> residue effects on <jats:italic>cis<\/jats:italic>\u2013<jats:italic>trans<\/jats:italic> isomerization. The following effects were observed: (a) aromatic residues immediately preceding Tyr\u2013Pro disfavor <jats:italic>cis<\/jats:italic> amide bonds, with <jats:italic>K<jats:sub>trans\/cis<\/jats:sub><\/jats:italic>= 5.7\u20138.0, <jats:italic>W<\/jats:italic> &gt; <jats:italic>Y<\/jats:italic> &gt; <jats:italic>F<\/jats:italic>; (b) proline residues preceding Tyr\u2013Pro lead to multiple species, exhibiting <jats:italic>cis<\/jats:italic>\u2013<jats:italic>trans<\/jats:italic> isomerization of either or both X\u2013Pro amide bonds; and (c) other residues exhibit similar values of <jats:italic>K<jats:sub>trans\/cis<\/jats:sub><\/jats:italic> (= 2.9\u20134.2), with Thr and protonated His exhibiting the highest fraction <jats:italic>cis<\/jats:italic>. \u03b2\u2010Branched and short polar residues were somewhat more favorable in stabilizing the <jats:italic>cis<\/jats:italic> conformation. Phosphorylation of serine at the <jats:italic>i<\/jats:italic> position modestly increases the stability of the <jats:italic>cis<\/jats:italic> conformer. In addition, the effect of the <jats:italic>i<\/jats:italic>+3 residue was examined in a limited series of peptides TYPZ. NMR data indicated that aromatic residues, Pro, Asn, Ala, and Val at the <jats:italic>i<\/jats:italic>+3 residue all favor <jats:italic>cis<\/jats:italic> amide bonds, with aromatic residues and Asn favoring more compact \u03d5 at Tyr<jats:sub><jats:italic>cis<\/jats:italic><\/jats:sub> and Ala and Pro favoring more extended \u03d5 at Tyr<jats:sub><jats:italic>cis<\/jats:italic><\/jats:sub>. <jats:sc>D<\/jats:sc>\u2010Alanine at the <jats:italic>i<\/jats:italic>+3 position particularly disfavors <jats:italic>cis<\/jats:italic> amide bonds. \u00a9 2005 Wiley Periodicals, Inc. Biopolymers 84: 192\u2013204, 2006<\/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 biopolymers@wiley.com<\/jats:p>","DOI":"10.1002\/bip.20382","type":"journal-article","created":{"date-parts":[[2005,10,6]],"date-time":"2005-10-06T11:46:30Z","timestamp":1128599190000},"page":"192-204","source":"Crossref","is-referenced-by-count":43,"title":["Effects of <i>i<\/i> and <i>i<\/i>+3 residue identity on <i>Cis\u2013Trans<\/i> isomerism of the aromatic<sub><i>i<\/i>+1<\/sub>\u2013prolyl<sub><i>i<\/i>+2<\/sub> amide bond: Implications for type VI \u03b2\u2010turn formation"],"prefix":"10.1002","volume":"84","author":[{"given":"Hai Yun","family":"Meng","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Krista M.","family":"Thomas","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aaron 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