Total Synthesis of Polyprenyl N-Glycolyl Lipid II as a Mycobacterial Transglycosylase Substrate
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- 作者：Fan-Chun Meng ; Kuo-Ting Chen ; Lin-Ya Huang ; Hao-Wei Shih ; Han-Hui Chang ; Fu-Yao Nien ; Pi-Hui Liang ; Ting-Jen R. Cheng ; Chi-Huey Wong ; Wei-Chieh Cheng
- 刊名：Organic Letters
- 出版年：2011
- 出版时间：October 7, 2011
- 年：2011
- 卷：13
- 期：19
- 页码：5306-5309
- 全文大小：838K
- 年卷期：v.13,no.19(October 7, 2011)
- ISSN：1523-7052
文摘
A feasible synthetic approach toward the Mycobacterium tuberculosis (Mtb) N-glycolyl lipid II-like molecule 1 is described. Compound 1 bears pendant undecaprenol and l-lysin moieties instead of the naturally occurring decaprenol and meso-diaminopimelic acid, which are not readily available. Functionalization of 1 with a fluorophore on the peptide side chain gave 14, which was found to be recognized as an Mtb TGase substrate. This result suggests it has tremendous utility for mechanistic studies, the characterization of mycobacterial enzymes, and mycobacterial TGase inhibitor evaluation.