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RESEARCH PRODUCT
Exploring new activating groups for reactive cysteine NCAs
David HuesmannLydia BraunThomas ReuterKristina KlinkerOlga SchäferMatthias Barzsubject
chemistry.chemical_classificationOrganic ChemistryLeaving group02 engineering and technologyElectron deficiency010402 general chemistry021001 nanoscience & nanotechnology01 natural sciencesBiochemistryCombinatorial chemistry0104 chemical sciencesAmino acidchemistry.chemical_compoundchemistryPolymerizationDrug DiscoveryThiolPeptide synthesisOrganic chemistryAmine gas treating0210 nano-technologyCysteinedescription
Abstract Due to its ability to reversibly crosslink proteins, cysteine has a unique role as an amino acid in nature. For controlled, asymmetric formation of disulfides from two thiols, one thiol needs to be activated. While few activating groups for cysteine have been proposed, they are usually not stable against amines making them unsuitable for solid phase peptide synthesis or amine initiated polymerization of α-amino acid-N-carboxy-anhydrides (NCAs). In this Letter we describe a series of new thiol activated cysteines, as well as their NCAs and explore the link between electron deficiency of the leaving group and control over NCA polymerization.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-03-01 | Tetrahedron Letters |