| Nitrilases catalyze key step to conformationally constrained GABA analogous gamma-amino acids in high optical purity. | |
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MedLine Citation:
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PMID: 17715966 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Five- and six-membered carbocyclic gamma-amino acids were prepared in high enantiomeric purity by nitrilase-mediated transformation of hitherto unreported gamma-amino nitriles. The nitrilases investigated reveal a strong enantiopreference for cis-isomers (up to 99% ee), whereas trans-isomers were available in up to 86% ee. The biocatalytic enantioselective syntheses of cis-3-aminocyclohexanecarboxylic acid (3b), trans-3-aminocyclohexanecarboxylic acids (4b, 6b, 8b) as well as trans-3-aminocylopentanecarboxylic acid (2b) are hereby reported for the first time. |
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Authors:
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Margit Winkler; Astrid C Knall; Martin R Kulterer; Norbert Klempier |
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Publication Detail:
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Type: Journal Article Date: 2007-08-23 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Sep |
Date Detail:
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Created Date: 2007-09-07 Completed Date: 2007-10-16 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 7423-6 Citation Subset: IM |
Affiliation:
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Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis* Aminohydrolases / chemistry*, metabolism Catalysis Hydrolysis Stereoisomerism gamma-Aminobutyric Acid / analogs & derivatives* |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 56-12-2/gamma-Aminobutyric Acid; EC 3.5.4.-/Aminohydrolases; EC 3.5.5.1/nitrilase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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