Journal
RAPID COMMUNICATIONS IN MASS SPECTROMETRY
Volume 21, Issue 2, Pages 141-152Publisher
JOHN WILEY & SONS LTD
DOI: 10.1002/rcm.2820
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Funding
- NCRR NIH HHS [P20 RR 20643, P20 RR020643] Funding Source: Medline
- NHLBI NIH HHS [P01 HL057278, P01 HL 57278] Funding Source: Medline
- NIA NIH HHS [R01 AG 23168, R01 AG023168, R01 AG023168-02] Funding Source: Medline
- NIDDK NIH HHS [P30 DK056341-07, P30 DK056341-06, P30 DK056341] Funding Source: Medline
- NATIONAL CENTER FOR RESEARCH RESOURCES [P20RR020643] Funding Source: NIH RePORTER
- NATIONAL HEART, LUNG, AND BLOOD INSTITUTE [P01HL057278] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES [P30DK056341] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE ON AGING [R01AG023168] Funding Source: NIH RePORTER
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We report a novel approach to derivatize the primary, secondary, and tertiary hydroxy group(s) of oxysterols with N,N-dimethylglycine (DMG) in the presence of both 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and 4-(N,N-dimethylamino)pyridine to yield their corresponding mono- or di-DMG esters. Eight oxysterols including 7-oxocholesterol, 5 alpha,6 alpha- and 5 beta,6 beta-epoxycholesterols, as well as 7 alpha-, 7 beta-, 24(S)-, 25-, and 27-hydroxycholesterols, were studied. Electrospray ionization tandem mass spectrometric characterization of these singly or doubly protonated derivatives demonstrates the presence of an informative fragmentation pattern for each oxysterol derivative. Potential dissociation pathways for the production of these unique fragmentation patterns are proposed and discussed. Collectively, these informative and unique fragmentation patterns allow rapid and direct discrimination of the identities of 7 alpha-, 7 beta-, 24(S)-, 25-, and 27-hydroxycholesterol isomers, as well as 5 alpha,6 alpha- and 5 beta,6 beta-epoxycholesterol isomers, thereby potentially providing a foundation for quantitative analysis of oxysterols in biological samples in combination with a chromatographic separation. Copyright (c) 2006 John Wiley & Sons, Ltd.
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