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

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Xu, Xiu-Hua, Trunkfield, Amy E., Bugg, Tim and Qing, Feng-Ling (2008) Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors. Organic & Biomolecular Chemistry, Vol.6 (No.1). pp. 157-161. doi:10.1039/b713068f

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Official URL: http://dx.doi.org/10.1039/b713068f

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Abstract

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.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
R Medicine > RS Pharmacy and materia medica
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Antiviral nucleosides -- Synthesis, Chemical inhibitors
Journal or Publication Title: Organic & Biomolecular Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Official Date: 2008
Dates:
DateEvent
2008Published
Volume: Vol.6
Number: No.1
Number of Pages: 5
Page Range: pp. 157-161
DOI: 10.1039/b713068f
Status: Peer Reviewed
Publication Status: Published
Funder: Guo jia zi ran ke xue ji jin wei yuan hui (China) (NSFC), China. Jiao yu bu (China. Ministry of Education), Shanghai Municipal Scientific Committee

Data sourced from Thomson Reuters' Web of Knowledge

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