12/14/14-Helix Formation in 2:1 α/β-Hybrid Peptides Containing Bicyclo[2.2.2]octane Ring Constraints

被引：7

作者：

Legrand, Baptiste ^{[1
]}

Andre, Christophe ^{[1
]}

Moulat, Laure ^{[1
]}

Didierjean, Claude ^{[2
]}

Hermet, Patrick ^{[3
]}

Bantignies, Jean-Louis ^{[4
]}

Martinez, Jean ^{[1
]}

Amblard, Muriel ^{[1
]}

Calmes, Monique ^{[1
]}

机构：

[1] Univ Montpellier, Inst Biomol Max Mousseron IBMM, CNRS, UMR 5247,ENSCM, 15 Ave Charles Flahault, F-34093 Montpellier 5, France

[2] Univ Lorraine, CNRS, UMR 7063, CRM2, Blvd Aiguilletes, F-54506 Vandoeuvre Les Nancy, France

[3] Univ Montpellier, Inst Charles Gerhardt Montpellier, CNRS, UMR 5253,ENSCM, Pl E Bataillon, F-34095 Montpellier 5, France

[4] Univ Montpellier, Lab Charles Coulomb, CNRS, UMR 5221, F-34095 Montpellier, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 34期

关键词：

12/14/14-helix; bicyclic beta-amino acids; helical structures; structure elucidation; alpha/beta-hybrid peptides; BETA-AMINO ACID; HELICAL SECONDARY STRUCTURES; CRYSTALLOGRAPHIC CHARACTERIZATION; STRUCTURAL-CHARACTERIZATION; HETEROGENEOUS BACKBONES; FOLDAMERS; RESIDUES; DESIGN; CONFORMATIONS; ALPHA; BETA;

D O I：

10.1002/chem.201602746

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly constrained beta-amino acid ABOC induces different types of helices in beta urea and 1:1 alpha/beta amide oligomers. The latter can adopt 11/9- and 18/16-helical folds depending on the chain length in solution. Short peptides alternating proteinogenic alpha-amino acids and ABOC in a 2: 1 alpha/beta repeat pattern adopted an unprecedented and stable 12/14/14-helix. The structure was established through extensive NMR, molecular dynamics, and IR studies. While the 1: 1 alpha-AA/ABOC helices diverged from the canonical alpha-helix, the helix formed by the 9-mer 2: 1 alpha/beta-peptide allowed the projection of the alpha-amino acid side chains in a spatial arrangement according to the alpha-helix. Such a finding constitutes an important step toward the conception of functional tools that use the ABOC residue as a potent helix inducer for biological applications.

引用

页码：11986 / 11990

页数：5

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