Conformations of Peptidomimetics Formed by SNAr Macrocyclizations: 13‐ to 16‐Membered Ring Systems[≠] Academic Article uri icon

abstract

  • The SNAr macrocyclization products 1a-d were designed to present two amino acids residues in β-turn conformations. Compound 1b in the series should give the most ideal fit because it could adopt a "turn-extended-pseudoturn" orientation. To test this hypothesis, compounds 1a-d were examined by a combination of CD and NMR spectroscopic techniques, and simulated by a computational approach that did not use constraints from spectroscopic data. Good correspondence between the spectroscopic data and the calculated conformations was obtained. All the compounds appear to be capable of adopting type I β-turns (or closely related states) but the bias towards this structure was most prevalent for the 14-membered macrocycle 1b, as predicted for the desired turn-extended-pseudoturn conformation.

altmetric score

  • 6

author list (cited authors)

  • Wang, Z., Jin, S., Feng, Y., & Burgess, K.

citation count

  • 8

publication date

  • November 1999

publisher