General Solution to the Preparation of β-Thiolated/Selenolated Amino Acids Via Visible Light Catalyzed Asymmetric Giese Reaction

Hongli Yin; Qingqing Zhou; Mengjie Zheng; Siyao Wang; Ping Wang

doi:10.1007/978-1-0716-2489-0_8

General Solution to the Preparation of β-Thiolated/Selenolated Amino Acids Via Visible Light Catalyzed Asymmetric Giese Reaction

Methods Mol Biol. 2022:2530:109-123. doi: 10.1007/978-1-0716-2489-0_8.

Authors

Hongli Yin¹, Qingqing Zhou¹, Mengjie Zheng¹, Siyao Wang¹, Ping Wang²

Affiliations

¹ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, China.
² Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, China. wangp1@sjtu.edu.cn.

PMID: 35761045
DOI: 10.1007/978-1-0716-2489-0_8

Abstract

Thiolated/selenolated amino acids are irreplaceable despite their rare abundance in proteins. They play critical roles in regulating the conformation and function of proteins and peptide design as well as bioconjugation. Furthermore, β-thiolated/selenolated amino acids are important motifs in native chemical ligation-dechalcogenation strategy for protein synthesis. However, a universal method to access enantiopure β-thiolated/selenolated amino acids has not been reported. Herein, we developed a practical strategy for the preparation of a variety of enantiopure β-thiolated/selenolated amino acids via photoredox-catalyzed Giese reaction.

Keywords: Giese reaction; Photoredox catalysis; β-thiolated/selenolated amino acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids* / chemistry
Catalysis
Light*
Peptides / chemistry
Proteins

Substances

Amino Acids
Peptides
Proteins