Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies
文献类型：期刊论文
| 作者 | Zhang, Yunqin; Hu, Yanlei; Liu, Shanshan; He, Haiqing; Sun, Roujing; Lu, Gang; Xiao, Guozhi |
| 刊名 | CHEMICAL SCIENCE
 |
| 出版日期 | 2022 |
| 卷号 | 13期号:26页码:7755-7764 |
| 关键词 | 1,2-CIS O-GLYCOSYLATION SELECTIVE SYNTHESIS CHEMICAL-SYNTHESIS OLIGOSACCHARIDE GALACTOSYLATION POLYSACCHARIDE ALKYNYLBENZOATES CONJUGATION ANTIBODIES CATALYSIS |
| DOI | 10.1039/d2sc02176e |
| 英文摘要 | The accessibility to long, branched and complex glycans containing many 1,2-cis glycosidic linkages with precise structures remains a challenging task in chemical synthesis. Reported here is an efficient, stereoselective and orthogonal one-pot synthesis of a tetradecasaccharide and shorter sequences from Lentinus giganteus polysaccharides with antitumor activities. The synthetic strategy consists of: (1) newly developed merging reagent modulation and remote anchimeric assistance (RMRAA) alpha-(1 -> 6)-galactosylation in a highly stereoselective manner, (2) DMF-modulated stereoselective alpha-(1 -> 3)-glucosylation, (3) RMRAA stereoselective alpha-(1 -> 6)-glucosylation, (4) several orthogonal one-pot glycosylations on the basis of N-phenyltrifluoroacetimidate (PTFAI) glycosylation, Yu glycosylation and ortho-(1-phenylvinyl)benzoate (PVB) glycosylation to streamline oligosaccharide synthesis, and (5) convergent [7 + 7] glycosylation for the final assembly of the target tetradecasaccharide. In particular, this new RMRAA alpha-galactosylation method has mild reaction conditions, broad substrate scopes and significantly shortened step counts for the heptasaccharide synthesis in comparison with 4,6-di-tert-butylsilyene (DTBS) directed alpha-galactosylation. Furthermore, DFT calculations shed light on the origins of remote anchimeric assistance effects (3,4-OBz > 3,4-OAc > 4-OBz > 3-OBz) of acyl groups. |
| WOS记录号 | WOS:000806467100001 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/74653]  |
| 专题 | 中国科学院昆明植物研究所 |
| 推荐引用方式 GB/T 7714 | Zhang, Yunqin,Hu, Yanlei,Liu, Shanshan,et al. Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies[J]. CHEMICAL SCIENCE,2022,13(26):7755-7764. |
| APA | Zhang, Yunqin.,Hu, Yanlei.,Liu, Shanshan.,He, Haiqing.,Sun, Roujing.,...&Xiao, Guozhi.(2022).Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies.CHEMICAL SCIENCE,13(26),7755-7764. |
| MLA | Zhang, Yunqin,et al."Total synthesis of Lentinus giganteus glycans with antitumor activities via stereoselective alpha-glycosylation and orthogonal one-pot glycosylation strategies".CHEMICAL SCIENCE 13.26(2022):7755-7764. |
入库方式： OAI收割
来源：昆明植物研究所
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