Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors

CORC > 上海有机化学研究所 > 中国科学院上海有机化学研究所 > 中科院有机氟化学重点实验室

	Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors
	Xu XH(徐修华) ; Amy E. Trunkfield ; Timothy D. H. Bugg ; Qing FL(卿凤翎)
刊名	Org. Biomol. Chem.
	2008
卷号	6 期号:1 页码:157-161
ISSN号	1477-0520
其他题名	Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors
通讯作者	卿凤翎
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.
学科主题	氟化学 ; 生命有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1039/b713068f
语种	英语
WOS记录号	WOS:000251580500028
公开日期	2013-02-22
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/17647]
专题	上海有机化学研究所_中科院有机氟化学重点实验室
推荐引用方式 GB/T 7714	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.
APA	徐修华,Amy E. Trunkfield,Timothy D. H. Bugg,&卿凤翎.(2008).Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors.Org. Biomol. Chem.,6(1),157-161.
MLA	徐修华,et al."Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors".Org. Biomol. Chem. 6.1(2008):157-161.