Synthesis of Chiral Spin-Labeled Amino Acids

被引：7

作者：

Vuong, Wayne ^{[1
]}

Mosquera-Guagua, Fabricio ^{[1
]}

Sanichar, Randy ^{[1
]}

McDonald, Tyler R. ^{[1
]}

Ernst, Oliver P. ^{[2
,3
]}

Wang, Lei ^{[4
]}

Vederas, John C. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

[2] Univ Toronto, Dept Biochem, Toronto, ON M5S 1A8, Canada

[3] Univ Toronto, Dept Mol Genet, Toronto, ON M5S 1A8, Canada

[4] Univ Calif San Francisco, Dept Pharmaceut Chem, San Francisco, CA 94158 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 24期

关键词：

EPR SPECTROSCOPY; RESOLUTION;

D O I：

10.1021/acs.orglett.9b04216

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled L-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.

引用

页码：10149 / 10153

页数：5

共 50 条

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