Design and Facile Synthesis of Neoglycolipids as Lactosylceramide Mimetics and Their Transformation into Glycoliposomes
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- HARADA Yoichiro
- Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University
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- MURATA Takeomi
- Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University CREST, Japan Science and Technology Agency
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- TOTANI Kazuhide
- Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University
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- KAJIMOTO Tetsuya
- Kyoto Pharmaceutical University
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- MASUM Shah Md.
- Department of Physics, Faculty of Science, Shizuoka University
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- TAMBA Yukihiro
- Department of Physics, Faculty of Science, Shizuoka University
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- YAMAZAKI Masahito
- Department of Physics, Faculty of Science, Shizuoka University
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- USUI Taichi
- Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University CREST, Japan Science and Technology Agency
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Abstract
Neoglycolipids composed of disaccharide glycoside and phospholipid were designed and prepared as mimetics of lactosylceramide. The lactosyl- and N-acetyllactosaminyl-phospholipids (Lac-DPPA and LacNAc-DPPA) were enzymatically synthesized from lactose and LacNAc respectively by cellulase-mediated condensation with 1,6-hexanediol, followed by conjugation of the resulting glycosides and dipalmitoylphosphatidyl choline (DPPC) mediated by Streptomyces phospholipase D. Alternatively, allyl β-lactoside was ozonolyzed to give an aldehyde, which was condensed with dipalmytoyl phosphatidyl ethanolamine to afford a second type of glycolipid (Lac-DPPE). NMR spectroscopy indicated that the neoglycolipids behave differently in different solvent systems. X-ray diffraction clearly showed that multilamellar vesicles (MLVs) of Lac-DPPE and Lac-DPPA-MLV are in the bilayer gel phase at 20 °C, whereas those of Lac-DPPE-MLV were in the lamellar liquid-crystalline phase at 50 °C. Differential scanning calorimetry showed that Lac-DPPE-MLV had complex thermotropic behavior depending on the incubation conditions. After a long incubation at 10 °C, endothermic transitions are observed at 39.6, 42.3 °C, and 42.9 °C. These neoglycolipids have the ability to trap calcein, a chelating derivative of fluorescein, in MLVs and showed specific binding to lectin in plate assays using fluorescently labeled compounds.
Journal
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- Bioscience, Biotechnology, and Biochemistry
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Bioscience, Biotechnology, and Biochemistry 69 (1), 166-178, 2005
Japan Society for Bioscience, Biotechnology, and Agrochemistry
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Details 詳細情報について
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- CRID
- 1390282681452995072
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- NII Article ID
- 130000030568
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- NII Book ID
- AA10824164
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- ISSN
- 13476947
- 09168451
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- NDL BIB ID
- 7237451
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- PubMed
- 15665482
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed