The distinctive nucleus of kainoid amino acids, (2S,3R)-(1)-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 a-chymotrypsin, reacted diastereo-, regio-,and enantioselectively to give the trans derivatives (1)-10a–c possessing the correct (2S,3R) configuration.Subsequently, the desired product (2S,3R)-(1)-6 could be obtained after well-establishedtransformations.
First Chemoenzymatic Synthesis of (1)-2-Carboxypyrrolidine-3-AceticAcid, the Nucleus of Kainoid Amino Acids / F., Felluga; C., Forzato; P., Nitti; G., Pitacco; Ghelfi, Franco; E., Valentin. - In: CHIRALITY. - ISSN 0899-0042. - STAMPA. - 24:2(2012), pp. 112-118. [10.1002/chir.21032]
First Chemoenzymatic Synthesis of (1)-2-Carboxypyrrolidine-3-AceticAcid, the Nucleus of Kainoid Amino Acids
GHELFI, Franco;
2012
Abstract
The distinctive nucleus of kainoid amino acids, (2S,3R)-(1)-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 a-chymotrypsin, reacted diastereo-, regio-,and enantioselectively to give the trans derivatives (1)-10a–c possessing the correct (2S,3R) configuration.Subsequently, the desired product (2S,3R)-(1)-6 could be obtained after well-establishedtransformations.
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