Stereochemical structures of synthesized and natural plasmalogalactosylceramides from equine brain.
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.
Publication Date: 1998-06-04 PubMed ID: 9610771
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- Journal Article
- Research Support
- Non-U.S. Gov't
Summary
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The research is focused on understanding the stereochemical structures of both synthesized and naturally occurring plasmalogalactosylceramides, found in horse brains. Techniques such as nuclear magnetic resonance spectroscopy and gas chromatography were used to determine the properties of these molecules.
Objective and Methodology
- The objective of this study was to identify the isomeric stereostructure of plasmalogalactosylceramide, a type of modified galactosylceramide found in equine brains. To do this, researchers chemically synthesized the plasmalo derivative from galactosylceramide.
- In order to confirm the presence of the cyclic acetal linkage, its position and length, the synthesized and natural variants were examined using proton nuclear magnetic resonance spectroscopy, fast-atom bombardment-mass spectrometry and two types of chromatography, namely gas chromatography-mass spectrometry and gas-liquid chromatography.
Findings
- The location of the acetal chain linked to the galactoside was determined using the homonuclear Overhauser effect, a technique related to NMR spectroscopy. This enabled the identification of connectivity between the cyclic acetal proton and ring proton(s) on the sugar part of the molecule.
- The research uncovered that two positional isomers of the acetal linkage existed, identified as 4,6-O-acetal and 3,4-O-acetal derivatives. These were the product of the prior acetalization reaction.
- The 4,6-O-acetal isomer was found to separate into two types, referred to as ‘endo’ and ‘exo’ acetal chains.
- Comparison of the NMR data of the synthesized derivative with the natural variant found in equine brain point to the latter being of an ‘endo’-type 4,6-O-acetal derivative.
Significance and Implications
- The findings provide crucial insights into the stereochemical structures of plasmalogalactosylceramides, whether synthesised or naturally occurring.
- Understanding the accurate structures of these molecules aids in understanding their roles and functions, which could lead to advancements in medical and scientific research on brain biochemistry.
- Investigations into such complex structures also advance the techniques used, making future research in this area more efficient and accurate.
Cite This Article
APA
Yachida Y, Kashiwagi M, Mikami T, Tsuchihashi K, Daino T, Akino T, Gasa S.
(1998).
Stereochemical structures of synthesized and natural plasmalogalactosylceramides from equine brain.
J Lipid Res, 39(5), 1039-1045.
Publication
Researcher Affiliations
- Department of Chemistry, Sapporo Medical University School of Medicine, Japan.
MeSH Terms
- Acetals / chemical synthesis
- Acetals / chemistry
- Acetals / isolation & purification
- Animals
- Brain Chemistry
- Carbohydrate Sequence
- Chromatography, Thin Layer
- Galactosylceramides / chemical synthesis
- Galactosylceramides / chemistry
- Galactosylceramides / isolation & purification
- Gas Chromatography-Mass Spectrometry
- Horses
- Magnetic Resonance Spectroscopy
- Molecular Sequence Data
- Stereoisomerism
Citations
This article has been cited 3 times.- Podbielska M, Levery SB, Hogan EL. The structural and functional role of myelin fast-migrating cerebrosides: pathological importance in multiple sclerosis. Clin Lipidol 2011 Apr;6(2):159-179.
- Parhi AK, Mootoo DR, Franck RW. Synthesis of the Mixed Acetal Segment of S-Glyceroplasmalopsychosine. Tetrahedron 2008 Oct 13;64(42):9821-9827.
- Hikita T, Tadano-Aritomi K, Iida-Tanaka N, Levery SB, Ishizuka I, Hakomori S. Cationic glycosphingolipids in neuronal tissues and their possible biological significance. Neurochem Res 2002 Aug;27(7-8):575-81.
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