铜绿假单胞菌O-抗原双脱氧乙酰氨基二糖的合成

包嘉龙; 田光宗; 吕国超; 秦春君; 邹小鹏; 胡静; 尹健

doi:10.13748/j.cnki.issn1007-7693.20260168

铜绿假单胞菌O-抗原双脱氧乙酰氨基二糖的合成

Synthesis of the Dideoxyacetamido Disaccharide of Pseudomonas aeruginosa O-Antigen

摘要

摘要:
目的利用化学方法立体选择性合成一种铜绿假单胞菌O-抗原双脱氧乙酰氨基二糖。
方法以苯硒基D-葡萄糖苷为起始原料，通过端基连接臂引入、C6位羟基脱氧及C2位叠氮基的还原胺化等关键步骤，高效构建奎诺糖胺受体砌块。随后，将其与D-岩藻糖胺糖基供体进行糖苷化反应，立体选择性地合成目标α-1,3-连接的二糖。
结果成功合成了目标二糖分子，所有中间体及终产物的结构均经核磁共振、高分辨质谱及旋光分析确证，产物纯度高。
结论双脱氧乙酰氨基二糖合成路线简洁高效，目标分子产物纯度高，可为该抗原的后续免疫学与生物活性研究提供物质基础。

Abstract:
OBJECTIVE To stereoselectively synthesize a dideoxyacetamido disaccharide of Pseudomonas aeruginosa O-antigen using chemical methods.
METHODS Starting from phenylseleno-D-glucoside, a quinovosamine acceptor building block was efficiently constructed through key steps including the introduction of an anomeric linker, deoxygenation at the C6-hydroxyl, and reductive amination of the C2-azido group. This acceptor was then coupled with a D-fucosamine glycosyl donor via glycosylation to stereoselectively furnish the target α-1,3-linked disaccharide.
RESULTS The target disaccharide was successfully synthesized. The structures of all intermediates and the final product were unambiguously confirmed by nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and optical rotation analysis. The product was obtained with high purity.
CONCLUSION The synthetic route for the dideoxyacetamido disaccharide is concise and efficient, affording the target product in high purity, which provides a material basis for subsequent immunological and bioactivity studies on this antigen.

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