Pseudodiproline (Pro-Cyp) Oligomers Fold into Helical Polyproline Type secondary structures
Jean-Baptiste Garsi1, Pedro M Aguiar1, Gilles Berger2
1Department of Chemistry, Université de Montréal, 1375 Ave. Thérèse-Lavoie-Roux, Montréal, H2V 0B3 QC Canada.
Abstract:
The synthesis and conformational properties of oligo-proline mimetics composed of dimeric and tetrameric Pro-Cyp constructs linked by a hydroxymethylene unit are reported. Oligomers were studied both in the solid state and in solution, unveiling right-handed helical conformation depending on the configuration of the vicinally substituted trans-cyclopentane carboxylic acid unit (Cyp). Unlike polyproline oligomers, the alternating synthetic Pro-Cyp counterparts are not stabilized by n-π* interactions but rely instead on the steric demands of the extended backbone conformation within the hydroxymethylene-linked Pro-Cyp repeating units.
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