Syntheses of phosphatidyl-β-d
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- 作者：Peter Greimel ; Milaine Lapeyre ; Yasuko Nagatsuka ; Yoshio Hirabayashi ; Yukishige Ito
- 关键词：Glucose ; Phospholipid ; Analogues ; Antibody
- 刊名：Bioorganic and Medicinal Chemistry
- 出版年：2008
- 出版时间：1 August 2008
- 年：2008
- 卷：16
- 期：15
- 页码：7210-7217
- 全文大小：509 K
文摘
Herein, we report the chemical syntheses of a series of phosphatidyl-β-d-glucoside (PtdGlc) analogues, including 6-O-Ac, sn-2-O-Me, phosphorothioate as well as phosphatidylgalactoside and -mannoside derivatives. In the key step, β-glycosyl H-phosphonate was condensed with enantiomerically pure diacylglycerol. Comparison of spectroscopic data with mono-acetylated PtdGlc from natural source confirmed the presence of an acetyl moiety at position 6. Furthermore, the reactivity of PtdGlc and its analogues toward monoclonal antibody ‘DIM21’ (MAb DIM21) was evaluated, revealing the crucial structural antigen features for successful MAb DIM21 binding.