Versatile Post-synthetic Modifications of Helical β-Peptide Foldamers Derived from a Thioether-Containing Cyclic β-Amino Acid

被引：5

作者：

Lim, Danim ^{[1
,2
]}

Lee, Wonchul ^{[1
,2
,4
]}

Hong, Jungwoo ^{[1
,2
]}

Gong, Jintaek ^{[1
,2
,5
]}

Choi, Jonghoon ^{[2
,3
]}

Kim, Jaewook ^{[1
,2
]}

Lim, Seolhee ^{[1
]}

Yoo, Sung Hyun ^{[1
,2
]}

Lee, Yunho ^{[2
,3
]}

Lee, Hee-Seung ^{[1
,2
]}

机构：

[1] Korea Adv Inst Sci & Technol KAIST, Dept Chem, 291 Daehak Ro, Daejeon 34141, South Korea

[2] Korea Adv Inst Sci & Technol, Ctr Multiscale Chiral Architectures CMCA, 291 Daehak Ro, Daejeon 34141, South Korea

[3] Seoul Natl Univ, Dept Chem, 1 Gwanak Ro, Seoul 08826, South Korea

[4] Kangwon Natl Univ, Inst Mol Sci & Fus Technol, Dept Chem, 1 Kangwondaehak Gil, Chunchon 24341, Gangwon, South Korea

[5] Sunchon Natl Univ, Dept Chem Educ, 255 Jungang Ro, Suncheon Si 57922, Jeonranam Do, South Korea

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 39期

基金：

新加坡国家研究基金会;

关键词：

amino acids; foldamers; peptidomimetics; post-synthetic modification; SECONDARY STRUCTURE; BETA-PEPTIDES; PROTEINS; DESIGN; CHEMISTRY;

D O I：

10.1002/anie.202305196

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We introduce a novel cyclic & beta;-amino acid, trans-(3S,4R)-4-aminotetrahydrothiophene-3-carboxylic acid (ATTC), as a versatile building block for designing peptide foldamers with controlled secondary structures. We synthesized and characterized a series of & beta;-peptide hexamers containing ATTC using various techniques, including X-ray crystallography, circular dichroism, and NMR spectroscopy. Our findings reveal that ATTC-containing foldamers can adopt 12-helical conformations similar to their isosteres and offer the possibility of fine-tuning their properties via post-synthetic modifications. In particular, chemoselective conjugation strategies demonstrate that ATTC provides unique post-synthetic modification opportunities, which expand their potential applications across diverse research areas. Collectively, our study highlights the versatility and utility of ATTC as an alternative to previously reported cyclic & beta;-amino acid building blocks in both structural and functional aspects, paving the way for future research in the realm of peptide foldamers and beyond.

引用

页数：5

共 41 条

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