Iminosugar C-glycoside analogues of ?-D-GlcNAc-1-phosphate: synthesis and bacterial transglycosylase inhibition.

ABSTRACT: We herein describe the first synthesis of iminosugar C-glycosides of ?-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 ?-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).

SUBMITTER: Hsu CH 

PROVIDER: S-EPMC4168788 | biostudies-literature |

REPOSITORIES: biostudies-literature