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First chemoenzymatic synthesis of (+)‐2‐carboxypyrrolidine‐3‐acetic acid, the nucleus of kainoid amino acids
Author(s) -
Felluga Fulvia,
Forzato Cristina,
Nitti Patrizia,
Pitacco Giuliana,
Ghelfi Franco,
Valentin Ennio
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.21032
Subject(s) - chemistry , diastereomer , chirality (physics) , acetic acid , stereochemistry , amino acid , organic chemistry , biochemistry , chiral symmetry , quantum mechanics , nambu–jona lasinio model , quark , physics
The distinctive nucleus of kainoid amino acids, (2 S ,3 R )‐(+)‐2‐carboxypyrrolidine‐3‐acetic acid 6 , was synthesized by a chemoenzymatic process, exploiting the diastereomeric cis / trans methyl pyroglutamate derivatives 10a , 10b , 10c / 11a , 11b , 11c 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 , 10b , 10c possessing the correct (2 S ,3 R ) configuration. Subsequently, the desired product (2 S ,3 R )‐(+)‐ 6 could be obtained after well‐established transformations. Chirality, 2012. © 2011 Wiley Periodicals, Inc.