Abstract
Washed cells of Rhodococcus erythropolis IFO 12540 were found to convert only the l-(+)-isomer of pantoyl lactone to the d-(—)-isomer in a racemic mixture of pantoyl lactone. Under suitable reaction conditions, the amount of d-(—)-pantoyl lactone synthesized was 18.2 mg/ml (94.4% enantiomer excess; molar yield, 90.5%). This conversion was suggested to proceed through the following successive reactions: first, the enzymatic oxidation of l-(+)-pantoyl lactone to ketopantoyl lactone; second, the rapid and spontaneous hydrolysis of the ketopantoyl lactone to ketopantoic acid; and then, the enzymatic reduction of the ketopantoic acid to d-(—)-pantoic acid. After the reaction d-(—)-pantoic acid could be lactonized by means of acid treatment. During the conversion, the d-(—)-isomer, which was initially present in the reaction mixture, did not undergo any modification.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- King H. L., Jr, Dyar R. E., Wilken D. R. Ketopantoyl lactone and ketopantoic acid reductases. Characterization of the reactions and purification of two forms of ketopantoyl lactone reductase. J Biol Chem. 1974 Aug 10;249(15):4689–4695. [PubMed] [Google Scholar]
- Lanzilotta R. P., Bradley D. G., McDonald K. M. Microbial reduction of ketopantoyl lactone to pantoyl lactone. Appl Microbiol. 1974 Jan;27(1):130–134. doi: 10.1128/am.27.1.130-134.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Wilken D. R., Dyar R. E. Analysis of stereochemistry of enzymically formed pantoyl lactone or pantoic acid by gas chromatography and circular dichroism. Anal Biochem. 1981 Mar 15;112(1):9–16. doi: 10.1016/0003-2697(81)90253-0. [DOI] [PubMed] [Google Scholar]
- Wilken D. R., King H. L., Jr, Dyar R. E. Ketopantoic acid and ketopantoyl lactone reductases. Stereospecificity of transfer of hydrogen from reduced nicotinamide adenine dinucleotide phosphate. J Biol Chem. 1975 Mar 25;250(6):2311–2314. [PubMed] [Google Scholar]