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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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:	Date Event 2008 Published
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

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