Iminosugar C-Glycoside Analogues of α-d-GlcNAc-1-Phosphate: Synthesis and Bacterial Transglycosylase Inhibition
The Journal of Organic Chemistry2014Vol. 79(18), pp. 8629–8637
Citations Over TimeTop 21% of 2014 papers
Che‐Hsiung Hsu, Mathias Schelwies, Sebastian Enck, Lin‐Ya Huang, Shih‐Hsien Huang, Yi‐Fan Chang, Ting-Jen Rachel Cheng, Wei‐Chieh Cheng, Chi‐Huey Wong
Abstract
We herein describe the first synthesis of iminosugar C-glycosides of α-D-GlcNAc-1-phosphate in 10 steps starting from unprotected D-GlcNAc. A diastereoselective intramolecular iodoamination-cyclization as the key step was employed to construct the central piperidine ring of the iminosugar and the C-glycosidic structure of α-D-GlcNAc. Finally, the iminosugar phosphonate and its elongated phosphate analogue were accessed. These phosphorus-containing iminosugars were coupled efficiently with lipophilic monophosphates to give lipid-linked pyrophosphate derivatives, which are lipid II mimetics endowed with potent inhibitory properties toward bacterial transglycosylases (TGase).
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