Zc. Wang et al., Conformations of peptidomimetics formed by SNAr macrocyclizations: 13-to 16-membered ring systems, CHEM-EUR J, 5(11), 1999, pp. 3273-3278
The SNAr macrocyclization products 1a-d were designed to present two amino
acids residues in beta-turn conformations. Compound 1b in the series should
give the most ideal fit because it could adopt a "turn - extended-pseudotu
rn" orientation. To test this hypothesis, compounds 1a-d were examined by a
combination of CD and NMR spectroscopic techniques, and simulated by a com
putational approach that did not use constraints from spectroscopic data. G
ood correspondence between the spectroscopic data and the calculated confor
mations was obtained. All the compounds appear to be capable of adopting ty
pe I beta-turns (or closely related states) but the bias towards this struc
ture was most prevalent for the 14-membered macrocycle 1b, as predicted for
the desired turn-extended-pseudo-turn conformation.