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高效基于D-葡萄糖胺的手性荧光标记试剂的开发以及甲基糖苷试剂的微波辅助β-选择性糖基化反应。

Development of highly potent D-glucosamine-based chiral fluorescent labeling reagents and a microwave-assisted beta-selective glycosidation of a methyl glycoside reagent.

作者信息

Ohrui Hiroshi, Kato Rumiko, Kodaira Teruhisa, Shimizu Hiroki, Akasaka Kazuaki, Kitahara Takeshi

机构信息

Graduate School of Life Sciences, Tohoku University, Sendai.

出版信息

Biosci Biotechnol Biochem. 2005 May;69(5):1054-7. doi: 10.1271/bbb.69.1054.

DOI:10.1271/bbb.69.1054
PMID:15914934
Abstract

We synthesized new chiral fluorescence labeling reagents having a 2,3-anthracenedicarboximide group from D-glucosamine, and it was possible to introduce target alcohols at the anomeric positions of the reagents with beta-selectivity by glycosidations. Especially, it was possible to use methyl glycoside reagent as a glycosyl donor with a Lewis acid and microwave irradiation, and it gave selectively beta-glycoside while the reaction without microwave irradiation gave alpha- and beta-mixed glycosides. Those reagents showed very high chiral discrimination ability, and they made it possible to separate the eight stereoisomers of 4,8,12,16-tetramethylheptadecanol by HPLC after derivatizations.

摘要

我们从 D-葡萄糖胺合成了具有 2,3-蒽二甲酰亚胺基团的新型手性荧光标记试剂，并且通过糖苷化反应能够以β-选择性将目标醇引入试剂的异头位置。特别是，使用甲基糖苷试剂作为糖基供体，在路易斯酸和微波辐射条件下，反应能选择性地生成β-糖苷，而无微波辐射时反应生成α-和β-混合糖苷。这些试剂表现出非常高的手性识别能力，通过衍生化后利用高效液相色谱法能够分离 4,8,12,16-四甲基十七醇的八种立体异构体。

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