AI Article Synopsis
- A chemoenzymatic process was used to synthesize the kainoid amino acid (2S,3R)-(+)-2-carboxypyrrolidine-3-acetic acid, utilizing specific methyl pyroglutamate derivatives as intermediates.
- Kinetic resolution mediated by α-chymotrypsin allowed for selective reactions that produced the desired trans derivatives, ensuring the correct stereochemistry of the final product.
- The target compound was obtained after a series of established transformations following the initial synthesis steps.
Article 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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| http://dx.doi.org/10.1002/chir.21032 | DOI Listing |
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First chemoenzymatic synthesis of (+)-2-carboxypyrrolidine-3-acetic acid, the nucleus of kainoid amino acids.
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February 2012
Department of Chemical and Pharmaceutical Sciences, University of Trieste, Trieste, Italy.
Article Synopsis
- A chemoenzymatic process was used to synthesize the kainoid amino acid (2S,3R)-(+)-2-carboxypyrrolidine-3-acetic acid, utilizing specific methyl pyroglutamate derivatives as intermediates.
- Kinetic resolution mediated by α-chymotrypsin allowed for selective reactions that produced the desired trans derivatives, ensuring the correct stereochemistry of the final product.
- The target compound was obtained after a series of established transformations following the initial synthesis steps.
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