Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inhibitors
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. ISSN 1477-0520Full text not available from this repository.
Official URL: http://dx.doi.org/10.1039/b713068f
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|
|Number of Pages:||5|
|Page Range:||pp. 157-161|
|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|
1 W. G. Struve, R. K. Sinha and F. C. Neuhaus, Biochemistry, 1966, 5,
Actions (login required)