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Thermodynamic Origin of Prolyl Peptide Bond Isomers by Eric S. Eberhardt; Stewart N. Loh; Ronald T. Raines is a Chemistry article available to read on EtoBox.

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The truns (Z) isomer of a typical peptide bond is favomd greatly over the cis Q isomer. Iu contrast, a trans bond involving the nitrogen atom of a proline residue is favored only slightly, and both isomers ate common in peptides and folded proteins.' &towing the thermodynamic origin for the relative stahility of X-Pm bond isomers is essential for understanding the conformation of peptides and proteins containing such bonds.2 The diffemnce in enthalpy for the cir and nwts isomers of X-Pm bonds in aqueous solution has heen reported to be zero for model pe~tides.~ or small (ca 1.2 kcal/mol) for poly(P~+Gly).~ The difference in free energy for the cis and rruns isomers of amides has been calculated with the 6-3 lG\*\* basis set of the Gaussian 82 ab initio program to be largely enthalpic in the gas phase: We have synthesized a peptide containing 'C-

Who reads Thermodynamic Origin of Prolyl Peptide Bond Isomers?

Author

Eric S. Eberhardt; Stewart N. Loh; Ronald T. Raines

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1993

Language

EN

Field

Chemistry (Physical Sciences)