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Stereochemical structures of synthesized and natural plasmalogalactosylceramides from equine brain
- Source :
- Journal of Lipid Research, Vol 39, Iss 5, Pp 1039-1045 (1998)
- Publication Year :
- 1998
-
Abstract
- Modified galactosylceramide with a long-chain cyclic acetal at the sugar moiety, plasmalogalactosylceramide, was isolated from equine brain. To identify the isomeric stereostructure of the natural product, the plasmalo derivative was chemically synthesized from galactosylceramide through acetalization. The presence of cyclic acetal linkage, the linked position and length of the acetal chain of the synthesized and natural products were determined by proton nuclear magnetic resonance spectroscopy and fast-atom bombardment–mass spectrometry, as well as gas chromatography–mass spectrometry and gas–liquid chromatography. The orientation of the acetal chain linked to galactoside was characterized by connectivity between the cyclic acetal proton and ring proton(s) on the sugar moiety using the homonuclear Overhauser effect. This revealed that, of the two positional isomers of the acetal linkage with 4,6-O-acetal and 3,4-O-acetal derivatives obtained from the acetalization reaction, the former positional isomer, separated into two spots, was identified to 'endo'- and 'exo'-type acetal chains. In comparison to the NMR data of the synthesized derivative, equine brain acetalized lipid was found to be an 'endo'-type 4,6-O-acetal derivative.—Yachida, Y., M. Kashiwagi, T. Mikami, K. Tsuchihashi, T. Daino, T. Akino, and S. Gasa. Stereochemical structures of synthesized and natural plasmalogalactosylceramides from equine brain. J. Lipid Res. 1998. 39: 1039–1045.
- Subjects :
- galactosylceramide
Magnetic Resonance Spectroscopy
Stereochemistry
Molecular Sequence Data
Galactosylceramides
QD415-436
Nuclear Overhauser effect
Ring (chemistry)
Biochemistry
Gas Chromatography-Mass Spectrometry
acetalization
chemistry.chemical_compound
Fatty aldehyde
Endocrinology
Acetals
Structural isomer
Animals
Horses
fatty aldehyde
Brain Chemistry
Natural product
Acetal
Stereoisomerism
Cell Biology
Galactoside
NMR
plasmaloglycolipid
chemistry
Carbohydrate Sequence
Proton NMR
Chromatography, Thin Layer
Subjects
Details
- ISSN :
- 00222275
- Volume :
- 39
- Issue :
- 5
- Database :
- OpenAIRE
- Journal :
- Journal of lipid research
- Accession number :
- edsair.doi.dedup.....43580369dc83abc2acd84c7a4a625f03