N-Acyl migration in ceramides

Journal of Lipid Research

Volumn 46, Issue 4, 2005, Pages 812-816

  Van Overloop, Helena ^a   Van Der Hoeven, Gerd ^a   Van Veldhoven, Paul P ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Anandamide; Ceramide kinase; Hydroxyoxazolidine; N acylethanolamine; O acylation

Indexed keywords

1 O ACYL SPHINGANINE; 3 O ACYL SPHINGANINE; CERAMIDE; CERAMIDE DERIVATIVE; CHLOROFORM; DICHLOROMETHANE; HYDROXYL GROUP; METHANOL; N ACETYL SPHINGENINE; UNCLASSIFIED DRUG; ACID;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; ROOM TEMPERATURE; STORAGE TEMPERATURE; ACYLATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; METABOLISM; PH; THIN LAYER CHROMATOGRAPHY;

ACIDS; ACYLATION; CERAMIDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE;

EID: 21744459888     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.D400034-JLR200     Document Type: Article

References (20)

1. Geeraert, L., G. P. Mannaerts, and P. P. Van Veldhoven. 1997. Conversion of dihydroceramide into ceramide: involvement of a desaturase. Biochem. J. 327: 125-132.
2. Welsh, I. H. 1949. Mechanism and stereochemical course of acyl migration in derivatives of ephedrine and ψ-ephedrine. J. Am. Chem. Soc. 71: 3500-3506.
3. Oliyai, R., and V. J. Stella. 1992. Kinetics and mechanism of isomerisation of cyclosporin A. Pharm. Res. 9: 617-622.
4. Oliyai, R., and V. J. Stella. 1995. Structural factors affecting the kinetics of O,N-acyl transfer in potential O-peptide prodrugs. Bioorg. Med. Chem. Lett. 5: 2735-2740.
5. Phillips, A. P., and R. Baltzly. 1947. Rearrangements between primary ethanolamides of carboxylic acids and the corresponding aminoethylesters. J. Am. Chem. Soc. 69: 200-204.
6. Schmid, H. H., and E. V. Berdyshev. 2002. Cannabinoid receptor-inactive N-acylethanolamines and other fatty acid amides: metabolism and function. Prostaglandins Leukot. Essent. Fatty Acids. 66: 363-376.
7. Dawson, R. M., N. Clarke, and R. H. Quarles. 1969. N- Acylphosphatidylethanolamine, a phospholipid that is rapidly metabolized during the early germination of pea seeds. Biochem. J. 114: 265-267.
8. Markey, S. P., T. Dudding, and T. C. Wang. 2000. Base- and acid-catalyzed interconversions of O-acyl- and N-acyl-ethanolamines: a cautionary note for lipid analyses. J. Lipid Res. 41: 657-662.
9. Norred, W. P., R. T. Riley, F. I. Meredith, S. M. Poling, and R. D. Plattner. 2001. Instability of N-acetylated fumonisin B1 (FA1) and the impact on inhibition of ceramide synthase in rat liver slices. Food Chem. Toxicol. 39: 1071-1078.
10. Desai, K., M. C. Sullards, J. Allegood, E. Wang, E. M. Schmelz, M. Hartl, H. U. Humpf, D. C. Liotta, Q. Peng, A. H. Merrill, Jr. 2002. Fumonisins and fumonisin analogs as inhibitors of ceramide synthase and inducers of apoptosis. Biochim. Biophys. Acta. 1585: 188-192.
11. Karlsson, K-A. 1970. On the chemistry and occurrence of sphingolipid long-chain bases. Chem. Phys. Lipids. 5: 6-43.
12. Carter, H. E., and Y. Fujino. 1956. Biochemistry of the sphingolipids. IX. Configuration of cerebrosides. J. Biol. Chem. 221: 879-884.
13. Taketomi, T., and N. Kawamura. 1970. Preparation of lysohematoside from hematoside of equine erythrocyte and its chemical and hemolytic properties. J. Biochem. (Tokyo). 68: 475-485.
14. Levade, T., N. Auge, R. J. Veldman, O. Cuvillier, A. Negre-Salvayre, and R. Salvayre. 2001. Sphingolipid mediators in cardiovascular cell biology and pathology. Circ. Res. 89: 957-968.
15. Hannun, Y. A., and L. M. Obeid. 2002. The ceramide-centric universe of lipid-mediated cell regulation: stress encounters of the lipid kind. J. Biol. Chem. 277: 25847-25850.
16. Menaldino, D. S., A. Bushnev, A. Sun, D. C. Liotta, H. Symolon, K. Desai, D. L. Dillehay, Q. Peng, E. Wang, J. Allegood, S. Trotman-Pruett, M. C. Sullards, and A. H. Merrill, Jr. 2003. Sphingoid bases and de novo ceramide synthesis: enzymes involved, pharmacology and mechanisms of action. Pharmacol. Res. 47: 373-381.
17. van Blitterswijk, W. J., A. H. van der Luit, R. J. Veldman, M. Verheij, and J. Borst. 2003. Ceramide: second messenger or modulator of membrane structure and dynamics? Biochem. J. 369: 199-211.
18. Buccoliero, R., and A. H. Futerman. 2003. The roles of ceramide and complex sphingolipids in neuronal cell function. Pharmacol. Res. 47: 409-419.
19. Cohen, S. A., and D. P. Michaud. 1993. Synthesis of a fluorescent derivatizing reagent, 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate, and its application for the analysis of hydrolysate amino acids via high-performance liquid chromatography. Anal. Biochem. 211: 279-287.
20. Lester, R. L., and R. C. Dickson. 2001. High-performance liquid chromatography analysis of molecular species of sphingolipid-related long chain bases and long chain base phosphates in Saccharomyces cerevisiae after derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate. Anal. Biochem. 298: 283-292.