Azaproline as a beta-turn-inducer residue opposed to proline

Azaproline (AzPro) is an analogue of proline containing a nitrogen atom in place of the C(alpha)H group. AzPro has been introduced in various model peptides, and especially in the Boc-Ala-AzPro-Ala-NHiPr tripeptide. The structural consequence of that modification has been investigated in solution by using IR and 1H NMR, with reference to the cognate proline-containing peptide. Contrary to proline, which induces beta-folding of the Pro-Ala sequence, azaproline apparently favors betaVI-folding of the Ala-AzPro one with high occurrence. Opening of the AzPro pyrazolidine ring to get N-methylazaalanine fundamentally does not change the structural properties of the azatripeptide, but allows the existence of open conformers to an extent depending on the solvent.