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

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• 作者：Che-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
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：September 19, 2014
• 年：2014
• 卷：79
• 期：18
• 页码：8629-8637
• 全文大小：428K
• ISSN：1520-6904

文摘

We herein describe the first synthesis of iminosugar C-glycosides of 伪-d-GlcNAc-1-phosphate in 10 steps starting from unprotected d-GlcNAc. A diastereoselective intramolecular iodoamination鈥揷yclization as the key step was employed to construct the central piperidine ring of the iminosugar and the C-glycosidic structure of 伪-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).