posted on 2015-12-17, 04:39authored byChe-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
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).