Preorganized Dipeptide Mimics as New Foldamer Building Blocks

Preorganised dipeptide mimics containing a 3,4-disubstituted oxazolidin-2-one, a flexible methylene group, and a 1,4-disubstituted triazole have been prepared in a few steps and high yield by copper-catalysed azide-alkyne cycloaddition (CuAAC). The combination of these three moieties allows the formation of a new dipeptide mimic that favours the formation of bent conformations, as we could demonstrate by IR and ROESY analysis. Rigid, flexible, rigid: the combination of a 3,4-disubstituted oxazolidin-2-one ring, a flexible methylene group and a 1,4-disubstituted triazole ring allows the formation of a new dipeptide mimic that favours the formation of bent conformations.