Strained-Cyclophane-Induced β-Turn Template: Design, Synthesis, and Spectroscopic Characterization
- 3 August 2004
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (18) , 3183-3186
- https://doi.org/10.1021/ol0488439
Abstract
[structure: see text] Three tetrapeptides incorporating a 14-membered (R(i+1), S(i+2)) cycloisodityrosine at the i + 1 and i + 2 positions were designed and synthesized. Conformational analysis by (1)H NMR and CD spectra as well as molecular modeling indicated that they all adopt a beta-turn conformation. While the CD spectrum of compound 2 is characteristic of the typical type-II beta-turn (maximum at approximately 200 nm and a minimum at approximately 220 nm), that of 1a (atropisomer of 2) is opposite in sign to the expected spectrum of the type-II beta-turn.Keywords
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