Document Detail

Enantiopure trans-3-arylaziridine-2-carboxamides: preparation by bacterial hydrolysis and ring-openings toward enantiopure, unnatural D-α-amino acids.
MedLine Citation:
PMID:  20812732     Owner:  NLM     Status:  MEDLINE    
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.
Roberto Morán-Ramallal; Ramón Liz; Vicente Gotor
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-09-24     Completed Date:  2011-01-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6614-24     Citation Subset:  IM    
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33071 Oviedo, Spain.
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MeSH Terms
Amino Acids / chemical synthesis*,  chemistry
Aziridines / chemical synthesis*,  chemistry
Molecular Structure
Rhodococcus / metabolism*
Reg. No./Substance:
0/Amino Acids; 0/Aziridines; 0/aziridine-2-carboxamide

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