New approach for characterization of lysosulfatide by TLC, fast atom bombardment mass spectrometry and NMR spectroscopy.
スポンサーリンク
概要
- 論文の詳細を見る
Thin layer chromatography of lysosulfatide showed anomalous Rf-values in contrast with such lysosphingolipids as glucopsychosine and galactopsychosine with neutral, acidic, and alkaline developing solvents. This was thought to be due to the presence of oppositely charged sulfate and amino groups in the lysosulfatide. In the negative mode of fast atom bombardment mass spectrometry, the lysosulfatide showed the pseudo molecular ion (M+H)- peak at m/z 540 and sulfate ion peak at m/z 97, whereas in the positive mode, it showed not only the pseudo molecular ion (M + H)+ peak at m/z 542, but also the major peaks of protonated psychosine at m/z 462 and fragment ions of dehydrated sphingosine at m/z 282 and 264. 13C-NMR signals of all carbons of lysosulfatide were determined by using distortionless enhancement by polarization transfer. The difference in chemical shifts of ring carbons of galactose residue between lysosulfatide and galactopsychosine was largest at C-3 (downfield shift), thereby indicating the location of the sulfate group to be at C-3 of galactose. This conclusion is supported by the 1H-NMR spectra of the lysosulfatide and galactopsychosine. Thus, the chemical structure of lysosulfatide was confirmed by fast atom bombardment mass spectrometry and 13C- and 1H-NMR spectroscopy. Furthermore, 13C-NMR signals of C-1 to C-5 of the sphingosine moiety showed significantly different chemical shifts between the lysosulfatide and galactopsychosine. These differences suggested that C-1 to C-5 of sphingosine might be influenced by intramolecular or inter-molecular interaction between the sulfate group of the galactose residue and the amino group of sphingosine. In particular, the order of the absolute value of difference in chemical shift (|Δδ|) being C-1>C-3>C-5 in the sphingosine between lysosulfatide and galactopsy-chosine suggested that the sulfate group might influence the carbons at C-1, -3, and -5, inducing a zigzag conformation of sphingosine in lysosulfatide. Also, the downfield shift of protons at C-1, -3, and -5 of sphingosine in lysosulfatide relative to sulfatide indicated that the removal of fatty acid from sulfatide might similarly induce a zigzag conformation of sphingosine in lysosulfatide. The interaction between the sulfate and amino groups was also suggested by the 1H-NMR spectra of the lysosulfatide and galactopsychosine, because the former showed no amino proton signal.
- 社団法人 日本生化学会の論文
著者
-
Hara Atsushi
Department Of Astrophysics Nagoya University
-
Sugiyama Eiko
Department Of Biochemistry Division Of Neuro-aging Research Center On Aging And Adaptation Shinshu U
-
Taketomi Tamotsu
Department Of Biochemistry Division Of Neuro-aging Research Center On Aging And Adaptation Shinshu U
-
Kutsukake Yukie
Department of Lipid Biochemistry, Institute of Cardiovascular Disease, Shinshu University School of Medicine
関連論文
- Dense Cores and Star-Formation Activities in the Chamaeleon Dark-Cloud Complex
- Evaluation of sphingolipids in vitreous bodies from a patient with Gaucher disease, using delayed extraction matrix-assisted laser desorption ionization time-of-flight mass spectrometry
- Application of delayed extraction matrix-assisted laser desorption ionization time-of-flight mass spectrometry for analysis of sphingolipids in cultured skin fibroblasts from sphingolipidosis patients
- Application of delayed extraction matrix-assisted laser desorption ionization time-of-flight mass spectrometry for analysis of sphingolipids in tissues from sphingolipidosis patients
- Chemical and Apoptotic Properties of Hydroxy-Ceramides Containing Long-Chain Bases with Unusual Alkyl Chain Lengths
- A Study of Dense Cloud Cores and Star Formation in Lupus: C^O J=1-0 Observations with NANTEN
- First Results of a CO Survey of the Large Magellanic Cloud with NANTEN; Giant Molecular Clouds as Formation Sites of Populous Clusters
- Preparation of Various Lysogangliosides Including Lyso-Fucosyl GM1 and Delayed Extraction Matrix-Assisted Laser Desorption Ionization Time-of -Flight Mass Spectrometric Analysis
- Rapid Method of Preparation of Lysoglycosphingolipids and Their Confirmation by Delayed Extraction Matrix-Assisted Laser Desorption Ionization Time-of-Flight Mass Spectrometry
- A New Derivation of the Extinction-to CO Column Density Ratio in the Chamaeleon I Dark Cloud
- Isolation of Reducing Oligosaccharide Chains from the Chondroitin/Dermatan Sulfate-Protein Linkage Region and Preparation of Analytical Probes by Fluorescent Labeling with 2-Aminobenzamide^1
- 老年期患者のせん妄に対するペロスピロンとリスペリドンの治療効果
- Attenuation of Kidney Injuries Maintains Serum Sulfatide Levels Dependent on Hepatic Synthetic Ability: A Possible Involvement of Oxidative Stress
- A convenient synthesis of 4- and 5-acetyltropolone.
- Synthesis and the spectral analysis of 4- and 6-(1-acetamido-3-(3,4,5-trimethoxyphenyl)propyl)-2-methoxytropones (B-ring-open analogues of colchicine).
- Long-term improvement of oxidative stress via kidney transplantation ameliorates serum sulfatide levels
- Rapid Method of Preparation of Lysoglycosphingolipids and Their Confirmation by Delayed Extraction Matrix-Assisted Laser Desorption Ionization Time-of-Flight Mass Spectrometry.
- New approach for characterization of lysosulfatide by TLC, fast atom bombardment mass spectrometry and NMR spectroscopy.