Conformational study of alanine and alpha-aminoisobutyric psi [NHCO]-retroamide peptide analogues

The minimum-energy conformations of N,N'-dimethyl-2-methylmalondiamide (2mMA) and N,N'-dimethyl-2-dimethylmalondiamide (2dmMA) have been computed using the AM1 method. The results show that molecules tend to form an intramolecular six-membered ring hydrogen-bond system. The same trend is observed in crystals of malonamide derivatives substituted in the central carbon atom. The results are also compared with previous molecular-mechanics calculations. The conformational trends of 2mMA and 2dmMA are very similar to those showed by N,N'-dimethylmalondiamide. Details of the computed conformational energy maps for 2mMA and 2dmMA compounds are given.