Switching and Conformational Fixation of Amides Through Proximate Positive Charges

被引：34

作者：

Bartuschat, Amelie L. ^{[1
]}

Wicht, Karina ^{[1
]}

Heinrich, Markus R. ^{[1
]}

机构：

[1] Univ Erlangen Nurnberg, Dept Chem & Pharm Pharmaceut Chem, Schuhstr 19, D-91052 Erlangen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 35期

关键词：

amide bond; ammonium ions; conformation; proline; rotamers; COLLAGEN TRIPLE-HELIX; PEPTIDE-BOND ISOMERIZATION; CIS-TRANS ISOMERISM; HYDROXYPROLINE RESIDUES; PROLINE RESIDUES; HYDROGEN-BONDS; AMINO-ACIDS; SIDE-CHAIN; STABILITY; PROLYL;

D O I：

10.1002/anie.201502474

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization.

引用

收藏

页码：10294 / 10298

页数：5

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