First chemoenzymatic synthesis of (+)-2-carboxypyrrolidine-3-acetic acid, the nucleus of kainoid amino acids |
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Authors: | Felluga Fulvia Forzato Cristina Nitti Patrizia Pitacco Giuliana Ghelfi Franco Valentin Ennio |
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Institution: | Department of Chemical and Pharmaceutical Sciences, University of Trieste, Trieste, Italy. ffelluga@units.it |
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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. |
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Keywords: | kainoids enzymatic hydrolysis kinetic resolution regioselectivity diastereoselectivity enantiomeric excess |
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