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学科主题: 生命有机化学
题名: Assembly of Naturally Occurring Glycosides, Evolved Tactics, and Glycosylation Methods
其他题名: 天然存在的糖苷的获取、发展策略及糖苷化方法
作者: Yu B(俞飚) ; Sun JS(孙建松) ; Yang XY(杨晓瑜)
通讯作者: 俞飚
刊名: Accounts Chem. Res.
发表日期: 2012
卷: 45, 期:8, 页:1227-1236
收录类别: SCI
部门归属: 中科院上海有机化学研究所
英文摘要: Glycosylation of proteins and lipids is critical to many life processes. Secondary metabolites (or natural products), such as flavonoids, steroids, triterpenes, and antibiotics, are also frequently modified with saccharides. The resulting glycosides include diverse structures and functions, and some of them have pharmacological significance. The saccharide portions of the glycosides often have specific structural characteristics that depend on the aglycones. These molecules also form heterogeneous "glycoform" mixtures where molecules have similar glycosidic linkages but the saccharides vary in the length and type of monosaccharide unit. Thus, It is difficult to purify homogeneous glycosides in appreciable amounts from natural sources. Chemical synthesis provides a feasible access to the homogeneous glycosides and their congeners. Synthesis of a glycoside involves the synthesis of the aglycone, the saccharide, the connection of these two parts, and the overall manipulation of protecting groups. However, most synthetic efforts to date have focused on the aglycones, treating the attachment of saccharides onto the aglycones as a dispensable topic. The synthesis of the aglycone and the synthesis of the saccharide belong to two independent categories of chemistry, and different types of the aglycones and saccharides pose as specific synthetic subjects in their own disciplines. The only reaction that integrates the broad chemistry of glycoside synthesis is the glycosidic bond formation between the saccharide and the aglycone. Focusing on this glycosylation reaction in this Account, we string together our experience with the synthesis of the naturally occurring glycosides. We briefly describe the synthesis of 18 glycosides, including glycolipids, phenolic glycosides, steroid glycosides, and triterpene glycosides. Each molecule represents a prototypical structure of a family of the natural glycosides with interesting biological activities, and we emphasize the general tactics for the synthesis of these diverse structures. We provide a rationale for four tactics for the synthesis of glycosides, based on the stage at which the glycosidic bond is formed between the saccharide and the aglycone. This choice of tactic determines the success or failure of a synthesis, and the flexibility and the overall efficiency of the synthesis as well. Toward the synthesis of heterogeneous glycoform mixtures, we discuss successive and random glycosylation reactions. Finally, we have developed two new glycosylation protocols that address the challenges in the glycosylation of aglycones that are poorly nucleophilic, extremely acid labile, or extremely electrophilic. One of these new protocols takes advantage of glycosyl trifluoroacetimidate donors, and a second protocol uses gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoate donors.
语种: 英语
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WOS记录号: WOS:000307696500006
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28561
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Yu B,Sun JS,Yang XY. Assembly of Naturally Occurring Glycosides, Evolved Tactics, and Glycosylation Methods[J]. Accounts Chem. Res.,2012,45(8):1227-1236.
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