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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 | 2014 Sep

REPOSITORIES: biostudies-literature

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

Hsu Che-Hsiung CH Schelwies Mathias M Enck Sebastian S Huang Lin-Ya LY Huang Shih-Hsien SH Chang Yi-Fan YF Cheng Ting-Jen Rachel TJ Cheng Wei-Chieh WC Wong Chi-Huey CH

The Journal of organic chemistry 20140829 18

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 lipoph ...[more]

PMID: 25137529

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