title: Iminosugar C-glycoside analogues of α-D-GlcNAc-1-phosphate: synthesis and bacterial transglycosylase inhibition.
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).
authors.affiliation: Genomics Research Center, Academica Sinica , Taipei 115, Taiwan.
authors.forename: Che-Hsiung
authors.initials: CH
authors.lastname: Hsu
authors.forename: Mathias
authors.initials: M
authors.lastname: Schelwies
authors.forename: Sebastian
authors.initials: S
authors.lastname: Enck
authors.forename: Lin-Ya
authors.initials: LY
authors.lastname: Huang
authors.forename: Shih-Hsien
authors.initials: SH
authors.lastname: Huang
authors.forename: Yi-Fan
authors.initials: YF
authors.lastname: Chang
authors.forename: Ting-Jen Rachel
authors.initials: TJ
authors.lastname: Cheng
authors.forename: Wei-Chieh
authors.initials: WC
authors.lastname: Cheng
authors.forename: Chi-Huey
authors.initials: CH
authors.lastname: Wong
mesh_terms: D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D016695:Glycosyltransferases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001426:Bacterial Proteins; D006027:Glycosides; D050111:Imino Sugars; C026146:N-acetylglucosamine-1-phosphate; D016695:Glycosyltransferases; D006026:Glycoside Hydrolases; D000117:Acetylglucosamine