Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine

被引：52

作者：

De Bo, Guillaume ^{[1
]}

Gall, Malcolm A. Y. ^{[1
]}

Kitching, Matthew O. ^{[1
]}

Kuschel, Sonja ^{[1
]}

Leigh, David A. ^{[1
]}

Tetlow, Daniel J. ^{[1
]}

Ward, John W. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 31期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

CYCLIC TRANSITION-STATES; MULTISTEP ORGANIC-SYNTHESIS; RIBOSOME NOBEL LECTURE; AMINO-ACIDS; CHEMICAL LIGATION; PROTEOLYTIC STABILITY; UNNATURAL PEPTIDES; GAMMA-PEPTIDES; ALPHA-PEPTIDE; DNA TEMPLATES;

D O I：

10.1021/jacs.7b05850

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report on the synthesis and operation of a three-barrier, rotaxane-based, artificial molecular machine capable of sequence-specific beta-homo (beta(3)) peptide synthesis. The machine utilizes nonproteinogenic beta(3)-amino acids, a class of amino acids not generally accepted by the ribosome, particularly consecutively. Successful operation of the machine via native chemical ligation (NCL) demonstrates that even challenging 15- and 19-membered ligation transition states are suitable for information translation using this artificial molecular machine. The peptide-bond-forming catalyst region can be removed from the transcribed peptide by peptidases, artificial and biomachines working in concert to generate a product that cannot be made by either machine alone.

引用

页码：10875 / 10879

页数：5

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