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学科主题: 氟化学 ; 生命有机化学
题名: Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors
其他题名: Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors
作者: Xu XH(徐修华) ; Amy E. Trunkfield ; Timothy D. H. Bugg ; Qing FL(卿凤翎)
通讯作者: 卿凤翎
刊名: Org. Biomol. Chem.
发表日期: 2008
卷: 6, 期:1, 页:157-161
收录类别: SCI
部门归属: 上海有机所有机所; 英国University of Warwick
英文摘要: Two gem-difluoromethylenated nucleoside moieties of liposidomycins, 3 and 4, were designed and synthesized. Compound 3 was assembled from lactol 5 and gem-difluoromethylenated nucleoside 6. In the synthesis of target molecule 4, the coupling of the trichloroacetimidate derivative of gem-difluoromethylenated furanose 7 with nucleoside 8 in the presence of TMSOTf gave the unexpected compound 16 when CH3CN was used as solvent. This results from acetonitrile acting as a nucleophile and participating in the glycosylation reaction. This unusual process may be correlated with the presence of the electron-withdrawing gem-difluoro substituents at the C-2 position of furanose. Compound 3 demonstrated 29% inhibition of MraY at 11.4 mM.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000251580500028
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17647
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Xu XH,Amy E. Trunkfield,Timothy D. H. Bugg,et al. Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors[J]. Org. Biomol. Chem.,2008,6(1):157-161.
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