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Azaproline as a β‐turn‐inducer residue opposed to proline

1998; Wiley; Volume: 52; Issue: 1 Linguagem: Inglês

10.1111/j.1399-3011.1998.tb00648.x

1399-3011

M. Zouikri, André Vicherat, A. Aubry, Michel Marraud, G. Boussard,

Neuropeptides and Animal Physiology

Abstract: Azaproline (AzPro) is an analogue of proline containing a nitrogen atom in place of the C α 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 1 H NMR, with reference to the cognate proline‐containing peptide. Contrary to proline, which induces β‐folding of the Pro‐Ala sequence, azaproline apparently favors βVI‐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.