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Issue 1, 2008
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Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors

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Abstract

Two gem-difluoromethylenated nucleoside moieties of liposidomycins, 3 and 4, were designed and synthesized. Compound 3 was assembled from lactol5 and gem-difluoromethylenated nucleoside6. In the synthesis of target molecule 4, the coupling of the trichloroacetimidate derivative of gem-difluoromethylenated furanose7 with nucleoside8 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.

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

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Supplementary files

Article information


Submitted
24 Aug 2007
Accepted
30 Oct 2007
First published
16 Nov 2007

Org. Biomol. Chem., 2008,6, 157-161
Article type
Paper

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

X. Xu, A. E. Trunkfield, T. D. H. Bugg and F. Qing, Org. Biomol. Chem., 2008, 6, 157
DOI: 10.1039/B713068F

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