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

3,4-Dihydro-2(1 H)-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 aza...

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Bibliographic Details
Published in:Tetrahedron 1998, Vol.54 (1), p.165-178
Main Authors: Torrini, Ines, Pagani Zecchini, Giampiero, Paglialunga Paradisi, Mario, Lucente, Gino, Mastropietro, Gaia, Gavuzzo, Enrico, Mazza, Fernando, Pochetti, Giorgio
Format: Article
Language:English
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Summary:3,4-Dihydro-2(1 H)-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-NH 2 ( 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. Synthesis, crystal structure, and conformation of the two azaTic derivatives 2 and 5 are reported. Similarities and differences with the related models containing the Tic and azaPro residue are discussed.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)10267-8