Factors affecting conformation in proline-containing peptides |
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Authors: | Taylor Carol M Hardré Renaud Edwards Patrick J B Park Jae H |
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Institution: | Institute of Fundamental Sciences, Massey University, Private Bag 11-222, Palmerston North, New Zealand. c.m.taylor@massey.ac.nz |
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Abstract: | reaction: see text] NMR was used to study the thermodynamics of the cis --> trans isomerization for prolyl amide bonds in the compounds shown. The magnitude of K(t/c) for C-terminal esters is greater than for the corresponding amides, signifying stronger backbone stereoelectronic effects in esters. Increasing the steric bulk of the N-terminal residue from Ac- to Ac-Gly- favors the trans conformation. Incorporation of a Phe residue N-terminal to Pro, however, shifts the equilibrium in favor of the cis conformation, via a stabilizing aromatic-proline interaction. |
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