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Effects of i and i+3 residue identity on Cis–Trans isomerism of the aromatici+1–prolyli+2 amide bond: Implications for type VI β-turn formation by Hai Yun Meng; Krista M. Thomas; Aaron E. Lee; Neal J. Zondlo is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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## Abstract __Cis__–__trans__ isomerization of amide bonds plays critical roles in protein molecular recognition, protein folding, protein misfolding, and disease. Aromatic–proline sequences are particularly prone to exhibit __cis__ amide bonds. The roles of residues adjacent to a tyrosine–proline residue pair on __cis__–__trans__ isomerism were examined. A short series of peptides XYPZ was synthesized and __cis__–__trans__ 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 __i__ residue effects on __cis__–__trans__ isomerization. The following effects were observed: (a) aromatic residues immediately preceding Tyr–Pro disfavor __cis__ amide bonds, with __K~trans/cis~__= 5.7–8.0, __W__ > __Y__ > __F__; (b) proline residues preceding Tyr–Pro lead to multiple species, exhibiting __cis__–__trans__ isomerization of either or both X–Pro amide bonds; and (c) other residues exhibit similar values of __K~trans/cis~__ (= 2.9–4.2), with Thr and protonated His exhibiting the highest fraction __cis__. β‐Branched and short polar residues were somewhat more favorable in stabilizing the __cis_

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Author

Hai Yun Meng; Krista M. Thomas; Aaron E. Lee; Neal J. Zondlo

Publisher

Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0006-3525)

Published

2005

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)