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Enantioselective bacterial hydrolysis of amido esters and diamides derived from (±)-trans-cyclopropane-1,2-dicarboxylic acid.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2014 Jan 28; Vol. 12 (4), pp. 615-23. - Publication Year :
- 2014
-
Abstract
- Different optically active amido esters, mixed acid esters, amido acids, and diamides derived from trans-cyclopropane-1,2-dicarboxylic acid were prepared from the commercially available diethyl (±)-trans-cyclopropane-1,2-dicarboxylate. The key step was the Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis of the corresponding racemic amide. The amidase present in this microorganism showed moderate to high enantioselectivity towards these substrates. In addition a simple and efficient Curtius rearrangement of some of the enzymatically prepared cyclopropanecarboxylic acids allowed us to obtain optically active β-aminocyclopropanecarboxylic acid derivatives with high yields and enantiomeric excesses.
- Subjects :
- Amidohydrolases chemistry
Cyclopropanes chemistry
Diamide chemistry
Dicarboxylic Acids chemistry
Esters chemistry
Hydrolysis
Molecular Conformation
Stereoisomerism
Amidohydrolases metabolism
Cyclopropanes metabolism
Diamide metabolism
Dicarboxylic Acids metabolism
Esters metabolism
Rhodococcus enzymology
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 12
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24292844
- Full Text :
- https://doi.org/10.1039/c3ob42066c