Synthesis of 3 10-helix-inducing constrained analogues of L-proline.
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.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, Quebec, Canada H3C 3J7. stephen.hanessian@umontreal.ca
Papeo
Gianluca
G
Fettis
Kamal
K
Therrien
Eric
E
Viet
Minh Tan Phan
MT
D000409:Alanine / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D013237:Stereoisomerism
D002264:Carboxylic Acids; D009842:Oligopeptides; D011392:Proline; D000409:Alanine