Many biologically important small molecules including acylhydrazides and N,N'-diacylhydrazines contain a (CO)-NR1-NR2-R moiety (where R can be another CO, R1 and R2 can be H, alkyl or aryl groups). In addition, peptidomimetic oligomers such as azapeptides and azatides contain CO-NR1-NR2-CO units embedded in their structure. The conformational properties of these molecules are often described based on the repulsion between their nitrogen lone pairs, which is inadequate. We are trying to understand the conformational properties of these molecules and identify if there is any role of noncovalent interactions mediated by their nitrogen and oxygen lone pairs. We aim to understand the conformational properties of acylhydrazides, diacylhydrazines and azapeptide model systems and use that knowledge to predict the probable secondary structures of azapeptidomimetic oligomers.
