The impact of pyrrolidine hydroxylation on the conformation of proline-containing peptides

CM Taylor, R Hardré, PJB Edwards

Index: Taylor, Carol M.; Hardre, Renaud; Edwards, Patrick J. B. Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1306 - 1315

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Citation Number: 57

Abstract

A series of eight dipeptides of the general formula Ac-Phe-Pro*-NHMe was synthesized and the thermodynamics of the cis→ trans isomerization about the central amide bond were studied by NMR. Pro* represents the following prolines: l-proline (Pro), l-trans-4- hydroxyproline (Hyp), l-cis-4-hydroxyproline (hyp), l-cis-4-methoxyproline (hyp [OMe]), l- trans-3-hydroxyproline (3-Hyp), l-cis-3-hydroxyproline (3-hyp), l-2, 3-trans-3, 4-cis-3, 4- ...

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