Synthesis of 3 10-helix-inducing constrained analogues of L-proline
Stephen Hanessian1, Gianluca Papeo, Kamal Fettis
1Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, Quebec, Canada H3C 3J7. stephen.hanessian@umontreal.ca
The Journal of Organic Chemistry
|July 17, 2004
Abstract:
A bicyclic indolizidinone carboxylic acid and a tricyclic constrained analogue of l-proline were synthesized and evaluated for their ability to induce helix formation as l-Ala tetrapeptides. Variable-temperature NMR, DMSO titration, CD spectra, and X-ray structure analyses, in conjunction with molecular modeling, confirmed the existence of 3(10)-helical motifs with di- and tetrapeptides of l-Ala.
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