Stereochemical structures of synthesized and natural plasmalogalactosylceramides from equine brain
| Autor: | Keiko Tsuchihashi, Toyoaki Akino, Motoi Kashiwagi, Takumi Daino, Shinsei Gasa, Takeshi Mikami, Youichi Yachida |
|---|---|
| Rok vydání: | 1998 |
| Předmět: |
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 |
| Zdroj: | Journal of Lipid Research, Vol 39, Iss 5, Pp 1039-1045 (1998) |
| ISSN: | 0022-2275 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|