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Iminosugar C‑Glycoside Analogues of α‑d‑GlcNAc-1-Phosphate: Synthesis and Bacterial Transglycosylase Inhibition
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)