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Enantioselective bacterial hydrolysis of amido esters and diamides derived from (±)-trans-cyclopropane-1,2-dicarboxylic acid.

Authors :
Hugentobler KG
Rebolledo F
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.

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