Synthesis an Secondary Structure of Alternate alpha,beta-Hybrid Peptides Containing Oxazolidin-2-one Moieties

Recently, several examples of foldamers have been reported containing a mixture of alpha,beta-amino acids in alternating order. In several cases, an increased resistance of the pseudopeptides against proteases was indicated in comparison to their native counterparts. Here, we report on the synthesis of novel foldamers with the general formula Boc-[(S)-beta3-hPhg-D-Oxd]n-OR, where (S)-beta3-hPhg is the abbreviation for (S)-beta3-homophenylglycine and D-Oxd that for trans-(4R,5S) 4-carboxy-5-methyl oxazolidin-2-one.