Facile removal of 4-methoxybenzyl protecting group from selenocysteine.

ABSTRACT: Historically, methods to remove the 4-methoxybenzyl (Mob)-protecting group from selenocysteine (Sec) in peptides have used harsh and toxic reagents. The use of 2,2'-dithiobis-5-nitropyridine (DTNP) is an improvement over these methods; however, many wash steps are required to remove the by-product contaminant 5-nitro-2-thiopyridine. Even with many washes, excess DTNP adheres to the peptide. The final product needs excess purification to remove these contaminants. It was recently discovered by our group that hindered hydrosilanes could be used to reduce Cys(Mob). We sought to apply a similar methodology to reduce Sec(Mob), which we expected to be even more labile. Here, we present a gentle and facile method for deprotection of Sec(Mob) using triethylsilane (TES), phenol, and a variety of ot

SUBMITTER: Jenny KA 

PROVIDER: S-EPMC6851407 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature