Copper(I/II)-Promoted Diverse Imidazo[1,2-α]pyridine Synthesis on Solid-Phase Bound DNA Oligonucleotides for Encoded Library Design
Marco Potowski, Ricarda Lüttig, Alexandros Vakalopoulos, Andreas Brunschweiger
Abstract
DNA-encoded libraries designed around heterocyclic scaffolds have proven highly productive in target-based screening. Here, we show the synthesis of imidazopyridines on a controlled pore glass-coupled DNA oligonucleotide for solid phase-initiated encoded library synthesis. The target compounds were synthesized by a variant of the A3 coupling reaction from aminopyridines, alkynes, and aldehydes promoted by copper(I/II) and furnished diverse substituted scaffolds with functionalities for library design. Although proceeding under forcing conditions, it produced minimal DNA damage.
Topics & Concepts
ChemistryOligonucleotideCombinatorial chemistryPyridineDNASolid-phase synthesisOligonucleotide synthesisDNA synthesisCopperAminopyridinesPhase (matter)Organic chemistryBiochemistryPeptideAdvanced biosensing and bioanalysis techniquesChemical Synthesis and AnalysisBacteriophages and microbial interactions