An Improved Method for the Preparation of Protected (R)-2-Methylcysteine: Solution-Phase Synthesis of a Glutathione Analogue

Authors

Douglas S. Masterson, University of Southern MississippiFollow
Brant L. Kedrowski, University of Wisconsin-Oshkosh
Amanda Blair, University of Southern Mississippi

Document Type

Article

Publication Date

12-1-2010

Department

Chemistry and Biochemistry

School

Mathematics and Natural Sciences

Abstract

A synthetic method for the preparation of (R)-2-methylcysteine that dramatically improves the overall yield of this important unnatural amino acid has been refined. The key steps in the preparation of (R)-2-methylcysteine were improved such that necessary intermediates were prepared in high yields and of sufficient purity to avoid the need for distillation or column chromatography. The ( R)-2-methylcysteine was prepared (> 90% ee) in appropriately protected form and used in a novel solution phase synthesis of a glutathione analogue.

Publication Title

Synlett

Issue

19

First Page

2941

Last Page

2943

Recommended Citation

Masterson, D. S., Kedrowski, B. L., Blair, A. (2010). An Improved Method for the Preparation of Protected (R)-2-Methylcysteine: Solution-Phase Synthesis of a Glutathione Analogue. Synlett(19), 2941-2943.
Available at: https://aquila.usm.edu/fac_pubs/8909