Sulfanylmethyldimethylaminopyridine as a Useful Thiol Additive for Ligation Chemistry in Peptide/Protein Synthesis
Kento Ohkawachi, Daishiro Kobayashi, Kyohei Morimoto, Akira Shigenaga, Masaya Denda, Kenzo Yamatsugu, Motomu Kanai, Akira Otaka
Abstract
Sulfanylmethyl-installed dimethylaminopyridine, 2-sulfanylmethyl-4-dimethylaminopyridine (2), has an acidic thiol group comparable to that in aryl thiols due to the formation of a zwitterion consisting of a thiolate anion and a pyridinium cation. It can be used as an additive for native chemical ligation. The alkyl thiol in 2 allows it to be used for the one-pot native chemical ligation–desulfurization protocol in peptide synthesis. The utility of 2 in the synthesis of cyclic peptides is demonstrated.
Topics & Concepts
Native chemical ligationChemistryZwitterionThiolPyridiniumChemical ligationAlkylPeptideLigationCysteineCombinatorial chemistryHydrazidePeptide synthesisOrganic chemistryMoleculeBiochemistryMolecular biologyEnzymeBiologyChemical Synthesis and AnalysisSulfur-Based Synthesis TechniquesClick Chemistry and Applications