title: First chemoenzymatic synthesis of (+)-2-carboxypyrrolidine-3-acetic acid, the nucleus of kainoid amino acids.
abstract: 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.
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, Trieste, Italy. ffelluga@units.it
authors.forename: Fulvia
authors.initials: F
authors.lastname: Felluga
authors.forename: Cristina
authors.initials: C
authors.lastname: Forzato
authors.forename: Patrizia
authors.initials: P
authors.lastname: Nitti
authors.forename: Giuliana
authors.initials: G
authors.lastname: Pitacco
authors.forename: Franco
authors.initials: F
authors.lastname: Ghelfi
authors.forename: Ennio
authors.initials: E
authors.lastname: Valentin
mesh_terms: D000085:Acetates / Q000138:chemical synthesis*; D000596:Amino Acids / Q000737:chemistry*; D002918:Chymotrypsin / Q000737:chemistry; D007608:Kainic Acid / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C574403:2-carboxypyrrolidine-3-acetic acid; D000085:Acetates; D000596:Amino Acids; D011759:Pyrrolidines; D002918:Chymotrypsin; C117608:alpha-chymotrypsin; C032519:pyrrolidine; D007608:Kainic Acid