Fluorinated and iodinated templates for syntheses of β-turn peptidomimetics

Various 2-fluoro-5-nitrobenzoic acids and the homocysteine derivative have been combined in solid phase syntheses of the peptidomimetic types . NMR and CD data collected for some of these compounds indicate that a transannular SO to HN hydrogen bond stabilizes β-turn conformations for the sulfones and one of the sulfoxide epimers. An extensive library of compounds was made and studied to test this assertion.