N-Terminal speciation for native chemical ligation
Oliver R. Maguire, Jiayun Zhu, William D. G. Brittain, Alexander Stephen Hudson, Steven L. Cobb, AnnMarie C. O’Donoghue
Abstract
Native chemical ligation (NCL) enables the chemical synthesis of peptides via reactions between N-terminal thiolates and C-terminal thioesters under mild, aqueous conditions at pH 7-8. Here we demonstrate quantitatively how thiol speciation at N-terminal cysteines and analogues varies significantly depending upon structure at typical pH values used in NCL.
Topics & Concepts
Native chemical ligationTerminal (telecommunication)ChemistryChemical ligationCombinatorial chemistryAqueous solutionGenetic algorithmLigationThiolCysteineChemical synthesisPeptideBiochemistryOrganic chemistryIn vitroBiologyComputer scienceMolecular biologyGeneticsEnzymeTelecommunicationsChemical Synthesis and AnalysisAntimicrobial Peptides and ActivitiesClick Chemistry and Applications