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