Document Detail


First chemoenzymatic synthesis of (+)-2-carboxypyrrolidine-3-acetic acid, the nucleus of kainoid amino acids.
MedLine Citation:
PMID:  22180179     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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. Chirality, 2011. © 2011 Wiley Periodicals, Inc.
Authors:
Fulvia Felluga; Cristina Forzato; Patrizia Nitti; Giuliana Pitacco; Franco Ghelfi; Ennio Valentin
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-12-19
Journal Detail:
Title:  Chirality     Volume:  -     ISSN:  1520-636X     ISO Abbreviation:  -     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2011-12-19     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 Wiley Periodicals, Inc.
Affiliation:
Department of Chemical and Pharmaceutical Sciences, University of Trieste, Trieste, Italy. ffelluga@units.it.
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