Fructose-Based Proline Analogues: Exploring the Prolyl trans/cis-Amide Rotamer Population in Model Peptides

被引：8
|
作者：
Cipolla, Laura [1 ]
Airoldi, Cristina [1 ]
Bini, Davide [1 ]
Gregori, Maria [1 ]
Marcelo, Filipa [2 ]
Jimenez-Barbero, Jesus [1 ,2 ]
Nicotra, Francesco [1 ]
机构：
[1] Univ Milano Bicocca, Dept Biosci & Biotechnol, I-20126 Milan, Italy
[2] CSIC, Ctr Invest Biol, Madrid 28040, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 01期
关键词：
Peptides; Peptidomimetics; Carbohydrates; Molecular modeling; Molecular dynamics; AMINO-ACID SCAFFOLDS; MOLECULAR-MECHANICS; SIDE-CHAIN; CONFORMATIONAL-ANALYSIS; BIOLOGICAL EVALUATION; COLLAGEN STABILITY; HAIRPIN FORMATION; DRUG DESIGN; BETA-TURNS; ISOMERIZATION;
D O I：
10.1002/ejoc.201000983
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A D-fructose moiety in which a D-proline ring has been engineered with a spiranic junction in the glycidic scaffold has been used as a proline mimetic. The bicyclic structure, which possesses high structural rigidity, was then included in model peptides to explore their prolyl cis/trans amide rotamer populations. Model peptide conformations were studied by molecular dynamics and NMR experiments.
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页码：128 / 136
页数：9
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