Solid-phase synthesis of 4-methylcarboxy-1,4-benzodiazepine-2,5-diones.
A solid-phase synthesis of 1,4-benzodiazepinone-2,5-diones is described. This new route can afford benzodiazepinone bearing a N-urethane-protected amine and a carboxylic acid function. This kind of building block is valuable as a dipeptide mimic or beta-turn mimetic, and it can be introduced in place of any amino acid in peptide synthesis. Using an "analytical probe" strategy, we optimized the synthesis of a model compound on SynPhase Lanterns. Therefore, the efficiency of several linkers was investigated.
Verdié
Pascal
P
Institut des Biomolecules Max Mousseron UMR 5247 CNRS, Universites Montpellier 1 et 2, Faculte de Pharmacie, 15 Avenue Charles Flahault BP 14491, 34093 Montpellier Cedex 5, France.
Subra
Gilles
G
Averland-Petit
Marie-Christine
MC
Amblard
Muriel
M
Martinez
Jean
J
D001570:Benzodiazepinones / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003432:Cross-Linking Reagents; D004151:Dipeptides; D018716:Molecular Mimicry
D001570:Benzodiazepinones; D003432:Cross-Linking Reagents; D004151:Dipeptides