Ontology highlight
ABSTRACT:
SUBMITTER: Shelton PM
PROVIDER: S-EPMC5731643 | biostudies-literature | 2017 Mar
REPOSITORIES: biostudies-literature
Shelton Patrick M M PM Weller Caroline E CE Chatterjee Champak C
Journal of the American Chemical Society 20170309 11
The C-terminal electrophilic activation of peptides by α-thioesterification requires strongly acidic conditions or complex chemical manipulations, which ultimately limit functional group compatibility and broad utility. Herein, we report a readily accessible N-mercaptoethoxyglycinamide (MEGA) solid-phase linker for the facile synthesis of latent peptide α-thioesters. Incubating peptide-MEGA sequences with 2-mercaptoethanesulfonic acid at mildly acidic pH yielded α-thioesters that were directly u ...[more]