168034-52-4Relevant academic research and scientific papers
Synthesis of all four diastereoisomers of 4-(carboxymethyl)proline, a conformationally constrained analogue of 2-aminoadipic acid
Pellicciari, Roberto,Arenare, Loredana,Caprariis, Paolo De,Natalini, Benedetto,Marinozzi, Maura,Galli, Alessandro
, p. 1251 - 1258 (2007/10/02)
The dirhodium(II) tetraacetate catalysed reaction of ethyl diazoacetate with 2,3-dihydropyrrole-2,2-dicarboxylate 5 afforded the useful 2-azabicyclohexane 6.Its conversion into the proline-γ-acetic acid equivalent 9 as well as into the four isomers constituting the 4-(carboxymethyl)proline 13 (16a-19a) whose absolute configuration was established by an alternative asymmetric synthesis of two of them is described.Preliminary data concerning the affinity of compounds 16a-19a for the NMDA site of the NMDA receptor complex are also reported.
