Dipeptide isostere 5, belonging to the class of 9-exo BTKa, was synthesised starting from R,R-tartaric acid and 4-nitro-1-(3-nitrophenyl)butan-1-one. The nine-membered lactam showed interesting structural features and was inserted in a 5-residue model peptide. The conformational properties of this modified peptide have been studied by NMR and molecular modelling, indicating that compound 5 acted as a reverse turn inducer.
3-Aza-8,10-dioxa-bicyclo[5.2.1]decane (9-exo BTKa) Carboxylic Acid as New Reverse Turn Inducer: Synthesis and Conformational Analysis of a Model Peptide / Scarpi, Dina; Stranges, D.; Trabocchi, Andrea; Guarna, Antonio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 62:(2006), pp. 1575-1582. [10.1016/j.tet.2005.11.008]
3-Aza-8,10-dioxa-bicyclo[5.2.1]decane (9-exo BTKa) Carboxylic Acid as New Reverse Turn Inducer: Synthesis and Conformational Analysis of a Model Peptide
SCARPI, DINA;TRABOCCHI, ANDREA;GUARNA, ANTONIO
2006
Abstract
Dipeptide isostere 5, belonging to the class of 9-exo BTKa, was synthesised starting from R,R-tartaric acid and 4-nitro-1-(3-nitrophenyl)butan-1-one. The nine-membered lactam showed interesting structural features and was inserted in a 5-residue model peptide. The conformational properties of this modified peptide have been studied by NMR and molecular modelling, indicating that compound 5 acted as a reverse turn inducer.
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