Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides

By Ying Wang, Joseph T. Paletta, Kathleen Berg, Erin Reinhart, Suchada Rajca, and Andrzej Rajca.

Published in Org Lett, 2014 Oct 17;16(20):5298-300.
PMID: 25324010. PMCID: PMC4201325 [Available on 2015/9/16] Link to publication page.

Core Facility: Membrane Protein Expression and Purification

Abstract

A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that l-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides.