岩藻糖基化硫酸软骨素五聚糖类似物 的合成

	岩藻糖基化硫酸软骨素五聚糖类似物的合成; Synthesis of Fucosylated Chondroitin Sulfate Pentasan Analogs
	姜玲
导师	秦红波
摘要	Fucosylated chondroitin sulfate is a novel glycosaminoglycan isolated from sea cucumbers. Its basic structure is composed of D-glucuronic acid (D-GlcA) and N-acetylamino-D-galactose (D-GalNAc). The chondroitin sulfate (CS) skeleton link branched-chain fucose sulfate (Fuc) by β- (1 → 3) glycosidic bonds. Studies have shown that FCS has good anticoagulant, antithrombotic, antitumor, and anti-inflammatory activities. This dissertation takes FCS oligosaccharide as research object, and studies of the synthesis of FCS pentasaccharide were carried out . It mainly includes the following three parts: The first chapter we reviewed the challenges and strategies of oligosaccharide synthesis. In the process of oligosaccharide synthesis, stereoselectivity of glycoside bond formation still exists, glycosylation of substrate with high density functional groups, and the differentiation of multiple functional groups by orthogonal protection to control the regional selectivity of glycosylation and downstream modifications(such as sulfation). We briefly described the protecting group strategy, donor group-containing leaving group strategy and oligosaccharide synthesis method strategy, It is hoped that the analysis of these strategies will provide guidance for the synthesis of FCS oligosaccharides. The second chapter mainly reviewed the glycosylation reaction conditions and protective group selection strategies during the synthesis of chondroitin sulfate (CS) oligosaccharides and fucosylated chondroitin sulfate oligosaccharides (FCS) in recent years, and it is expected that some experience can be used for the synthesis of FCS oligosaccharides. The third chapter mainly discussed the synthesis of FCS pentasaccharide. β-D-pentaacetylglucose, α-methylglucose, D-galactose and L-fucose are used as raw materials to easily synthesize four monosaccharide blocks, and then use α-methylglucose acceptor 3-62 and 2-azido-galactose donor 3-42 to obtain disaccharide 3-63 stereoselectively under NIS, TfOH conditions, selectively remove Lev protective group to obtain disaccharide acceptor, and then The glycosylation reaction of with glucose donor 3-13 can obtain the main chain trisaccharide 3-65, and then oxidize the 6-position of chondroitin trisaccharide glucose to methyl ester 3-67, and after that selectively remove Alloc protective group of the 3-position to obtain the trisaccharide acceptor 3-68. Its glycosylated with the fucose donor 3-36 to obtain pentasaccharide. In this synthesis route, we adopt a 3 + 2 synthesis strategy, synthesizing the chondroitin main chain at first, and then connecting it with fucose branch chain. After 37 steps, the synthesis of FCS pentasaccharide was completed with a total yield of 4.2%.
	2020-05
文献类型	学位论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74137
专题	昆明植物所硕博研究生毕业学位论文
推荐引用方式 GB/T 7714	姜玲. 岩藻糖基化硫酸软骨素五聚糖类似物的合成, Synthesis of Fucosylated Chondroitin Sulfate Pentasan Analogs[D],2020.

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