Title

Microwave-Assisted Cleavage of Cysteine Perfluoroaryl Thioethers

Authors

Taylor N. Bednar, Dickinson College
Alissa R. Resnikoff, Dickinson College
Jason Gavenonis, Dickinson College

Roles

Student author: Taylor Bednar
Student author: Alissa Resnikoff

Document Type

Article

Publication Date

4-29-2020

Department

Chemistry

Language

English

Publication Title

Amino Acids

Abstract

The cysteine- perfluoroarene SNAr reaction allows for the sequence-specific attachment of dyes and affinity tags to peptides and proteins. However, while many methods exist for the desulfuration of native and functionalized cysteine residues, there are no reports of their application to perfluoroarylated cysteines. Herein we report both the hydrogenolysis of a perfluoroarylated cysteine to alanine and elimination to dehydroalanine, reactions that are both accelerated by microwave irradiation.

Comments

Published as:
Bednar, Taylor N., Alissa R. Resnikoff, and Jason Gavenonis. "Microwave-Assisted Cleavage of Cysteine Perfluoroaryl Thioethers." Amino Acids (Article published online April 29, 2020). https://doi.org/10.1007/s00726-020-02846-z

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DOI

10.1007/s00726-020-02846-z

Recommended Citation

Bednar, Taylor N.; Resnikoff, Alissa R.; and Gavenonis, Jason, "Microwave-Assisted Cleavage of Cysteine Perfluoroaryl Thioethers" (2020). Dickinson College Faculty Publications. Paper 1393.
https://scholar.dickinson.edu/faculty_publications/1393