Late-stage peptide modification and macrocyclization enabled by tertiary amine catalyzed tryptophan allylation
Yuyang Liu, Guofeng Li, Wen Ma, Guangjun Bao, Yiping Li, Zeyuan He, Zhaoqing Xu, Rui Wang, Wangsheng Sun
Abstract
2' pathway between the N1 position of the indole ring of Trp and Morita-Baylis-Hillman (MBH) carbonates. Using this method that proceeds under mild conditions, we demonstrated an extremely broad scope of Trp-containing peptides and MBH carbonates to prepare a series of peptide conjugates and cyclic peptides. The reaction is amenable to either solid-phase (on resin) or solution-phase conditions. In addition, the modified peptides can be further conjugated with other biomolecules at Trp, providing a new handle for bioconjugation.
Topics & Concepts
TryptophanChemistryCatalysisAmine gas treatingCombinatorial chemistryPeptideTertiary amineOrganic chemistryAmino acidBiochemistryChemical Synthesis and AnalysisClick Chemistry and ApplicationsMicrobial Natural Products and Biosynthesis