1357487-91-2Relevant academic research and scientific papers
First chemoenzymatic synthesis of (+)-2-carboxypyrrolidine-3-acetic acid, the nucleus of kainoid amino acids
Felluga, Fulvia,Forzato, Cristina,Nitti, Patrizia,Pitacco, Giuliana,Ghelfi, Franco,Valentin, Ennio
, p. 112 - 118 (2012/02/16)
The distinctive nucleus of kainoid amino acids, (2S,3R)-(+)-2- carboxypyrrolidine- 3-acetic acid 6, was synthesized by a chemoenzymatic process, exploiting the diastereomeric cis/ trans methyl pyroglutamate derivatives 10a-c/11a-c as key intermediates. These mixtures, when subjected to a kinetic resolution mediated by α-chymotrypsin, reacted diastereo-, regio-, and enantioselectively to give the trans derivatives (+)-10a-c possessing the correct (2S,3R) configuration. Subsequently, the desired product (2S,3R)-(+)-6 could be obtained after well-established transformations.
