Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent.
Simple methods for determining the enantiomeric purity of mevalonolactone and linalool by NMR using the chiral shift reagent Eu(hfc)3 are reported. These methods are more reliable than polarimetry and require only a few milligrams of sample to detect as little as 2% of the minor enantiomer. The accu...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Elsevier
1982-05-01
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| Series: | Journal of Lipid Research |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S002222752038130X |
| _version_ | 1831766316297486336 |
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| author | W K Wilson T J Scallen C U Morrow |
| author_facet | W K Wilson T J Scallen C U Morrow |
| author_sort | W K Wilson |
| collection | DOAJ |
| description | Simple methods for determining the enantiomeric purity of mevalonolactone and linalool by NMR using the chiral shift reagent Eu(hfc)3 are reported. These methods are more reliable than polarimetry and require only a few milligrams of sample to detect as little as 2% of the minor enantiomer. The accuracy of these methods is limited primarily by spectral resolution for samples of high enantiomeric excess and by errors inherent in measuring peak intensities for samples of low enantiomeric excess. The Cornforth synthesis (Cornforth, R. M., J. W. Cornforth, and G. Popják. 1962. Tetrahedron. 18: 1351-1354) of (S)-mevalonolactone from (R)-linalool has been improved and shown to proceed with negligible racemization. |
| first_indexed | 2024-12-22T06:19:18Z |
| format | Article |
| id | doaj.art-0b72975f46f347e8b92fcd999dfa3e22 |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-22T06:19:18Z |
| publishDate | 1982-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-0b72975f46f347e8b92fcd999dfa3e222022-12-21T18:35:59ZengElsevierJournal of Lipid Research0022-22751982-05-01234645652Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent.W K WilsonT J ScallenC U MorrowSimple methods for determining the enantiomeric purity of mevalonolactone and linalool by NMR using the chiral shift reagent Eu(hfc)3 are reported. These methods are more reliable than polarimetry and require only a few milligrams of sample to detect as little as 2% of the minor enantiomer. The accuracy of these methods is limited primarily by spectral resolution for samples of high enantiomeric excess and by errors inherent in measuring peak intensities for samples of low enantiomeric excess. The Cornforth synthesis (Cornforth, R. M., J. W. Cornforth, and G. Popják. 1962. Tetrahedron. 18: 1351-1354) of (S)-mevalonolactone from (R)-linalool has been improved and shown to proceed with negligible racemization.http://www.sciencedirect.com/science/article/pii/S002222752038130X |
| spellingShingle | W K Wilson T J Scallen C U Morrow Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent. Journal of Lipid Research |
| title | Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent. |
| title_full | Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent. |
| title_fullStr | Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent. |
| title_full_unstemmed | Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent. |
| title_short | Determination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent. |
| title_sort | determination of the enantiomeric purity of mevalonolactone via nmr using a chiral lanthanide shift reagent |
| url | http://www.sciencedirect.com/science/article/pii/S002222752038130X |
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