Factors affecting conformation in proline-containing peptides

被引:59
|
作者
Taylor, CM
Hardré, R
Edwards, PJB
Park, JH
机构
[1] Massey Univ, Inst Fundamental Sci, Palmerston North, New Zealand
[2] Univ Auckland, Dept Chem, Auckland, New Zealand
关键词
D O I
10.1021/ol035711r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4413 / 4416
页数:4
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