Topographically constrained aromatic α-aza-amino acids. Synthesis, molecular structure, and conformation of two azaTic derivatives

Article abstract of DOI:10.1016/S0040-4020(97)10267-8

3,4-Dihydro-2(1H)-phthalazinecarboxylic acid (azaTic) is a new conformationally restricted analogue of phenylalanine which, due to its α-aza-nature, should allow, in addition to the topographical control typical of the Tic residue, a definite local perturbation of the backbone conformation. Two azaTic models, namely azaTic-NH₂ (2) and MeCO-azaTic-NHMe (5), have been synthesized and their conformation has been determined and compared to that of the related Tic and azaPro models.