Michael Addition Reaction between Dehydroalanines and Phosphites Enabled the Introduction of Phosphonates into Oligopeptides
Changjun Yu, E Ruiyao, Yingying An, Xiaomin Guo, Guangjun Bao, Yiping Li, Junqiu Xie, Wangsheng Sun
Abstract
A method for introducing a range of phosphonates into oligopeptides through a Michael addition reaction between dehydroalanine and phosphite is presented. The method offers a mild, cheap, and straightforward approach to peptide phosphorylation that has potential applications in chemical biology and medicinal chemistry. Moreover, the introduction of a phosphonate group into short antibacterial peptides is described to demonstrate its utility, leading to the discovery of phosphonated antibacterial peptides with potent broad-spectrum antibacterial activity.
Topics & Concepts
ChemistryDehydroalaninePhosphonateOligopeptideCombinatorial chemistryAntibacterial peptidePeptideAntimicrobialStereochemistryOrganic chemistryAntibacterial activityBiochemistryBacteriaBiologyGeneticsChemical Synthesis and AnalysisClick Chemistry and ApplicationsRNA and protein synthesis mechanisms