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

1998; Elsevier BV; Volume: 54; Issue: 1-2 Linguagem: Inglês

10.1016/s0040-4020(97)10267-8

1464-5416

Ines Torrini, Giampiero Pagani Zecchini, Mario Paglialunga Paradisi, Gino Lucente, Gaia Mastropietro, E. Gavuzzo, Fernando Mazza, G. Pochetti,

Axial and Atropisomeric Chirality Synthesis

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.