Reduction of cysteine-S-protecting groups by triisopropylsilane.

ABSTRACT: Triisopropylsilane (TIS), a hindered hydrosilane, has long been utilized as a cation scavenger for the removal of amino acid protecting groups during peptide synthesis. However, its ability to actively remove S-protecting groups by serving as a reductant has largely been mischaracterized by the peptide community. Here, we provide strong evidence that TIS can act as a reducing agent to facilitate the removal of acetamidomethyl (Acm), 4-methoxybenzyl (Mob), and tert-butyl (Bu^t ) protecting groups from cysteine (Cys) residues in the presence of trifluoroacetic acid (TFA) at 37 °C. The lability of the Cys protecting groups in TFA/TIS (98/2) in this study are in the order: Cys(Mob) > Cys(Acm) > Cys(Bu^t ), with Cys(Mob) being especially labile. Unexpectedly, we found that T

SUBMITTER: Ste Marie EJ 

PROVIDER: S-EPMC6773273 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature