Topographically constrained aromatic α-aza-amino acids. Part 2. New azaTic-containing peptides: Synthesis, conformation, and intramolecular NH…N interaction
✍ Scribed by Ines Torrini; Giampiero Pagani Zecchini; Mario Paglialunga^Paradisi; Gaia Mastropietro; Gino Lucente; Enrico Gavuzzo; Fernando Mazza
- Book ID
- 104209115
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 765 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
The new pseudedipeptide Boc-azaTic-Leu-OMe (I), incorporating the conformationally and topographically constrained 3,4-dihydro-2(IH)-phthalazinecurboxylic acid (azaTic) residue, has been synthesized together with the three related models Boc-azaTic-NHMe (3), MeCO-azaTic-Gly-OMe (4), and azaTic-Leu-OMe (6). Both the epimers of 1, generated by Ol~OSite absolute configuration at an azaTic nitrogen stereogenic centre, have been found in the asymmetric unit of the crystal.The conformational perturbations, deriving by the introduction of the azaTic residue into a peptide backbone, are described and the nature of the Nil..-N interaction, which gives rise to a typical backbone folding closing a 5-membered ring, has been studied.