Building β-Peptide H10/12 Foldamer Helices with Six-Membered Cyclic Side-Chains: Fine-Tuning of Folding and Self-Assembly

被引：67

作者：

Mandity, Istvan M. ^{[1
]}

Fueloep, Livia ^{[2
]}

Vass, Elemer ^{[3
]}

Toth, Gabor K. ^{[2
]}

Martinek, Tamas A. ^{[1
]}

Fueloep, Ferenc ^{[1
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

[2] Univ Szeged, Dept Med Chem, H-6720 Szeged, Hungary

[3] Eotvos Lorand Univ, Dept Organ Chem, Inst Chem, H-1117 Budapest, Hungary

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 23期

关键词：

LYOTROPIC LIQUID-CRYSTALS; SECONDARY STRUCTURE; DESIGN; ASSOCIATION; FAMILY; ACIDS; NMR; CD;

D O I：

10.1021/ol102494m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ability of the beta-peptidic H10/12 helix to tolerate side-chains containing six-membered alicyclic rings was studied. cis-2-Aminocyclohex-3-ene carboxylic acid (cis-ACHEC) res dues afforded H10/12 helix formation with alternating backbone configuration. Conformational polymorphism was observed for the alternating cis-ACHC hexamer, where chemical exchange takes place between the major left-handed H10/12 helix and a minor folded conformation. The hydrophobically driven self-assembly was achieved for the cis-ACHC-containing helix which was observed as vesicles similar to 100 nm in diameter.

引用

页码：5584 / 5587

页数：4

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