| Enantiopure trans-3-arylaziridine-2-carboxamides: preparation by bacterial hydrolysis and ring-openings toward enantiopure, unnatural D-α-amino acids. | |
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MedLine Citation:
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PMID: 20812732 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural d-α-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined. |
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Authors:
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Roberto Morán-Ramallal; Ramón Liz; Vicente Gotor |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Oct |
Date Detail:
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Created Date: 2010-09-24 Completed Date: 2011-01-04 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: 6614-24 Citation Subset: IM |
Affiliation:
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Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33071 Oviedo, Spain. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis*,
chemistry Aziridines / chemical synthesis*, chemistry Biocatalysis Hydrolysis Molecular Structure Rhodococcus / metabolism* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Aziridines; 0/aziridine-2-carboxamide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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