68690-45-9Relevant academic research and scientific papers
Synthesis of a comprehensive polyprenol library for the evaluation of bacterial enzyme lipid substrate specificity
Wu, Baolin,Woodward, Robert,Wen, Liuqing,Wang, Xuan,Zhao, Guohui,Wang, Peng George
, p. 8162 - 8173 (2014/01/06)
Polyprenols, a universal class of glycan-carrier lipids, play important roles in glycan biosynthesis in wide variety of living organisms. The chemical synthesis of natural polyisoprenols such as undecaprenol and dolichols, and even more so the synthesis o
Staphylococcus aureus penicillin-binding protein 2 can use depsi-lipid ii derived from vancomycin-resistant strains for cell wall synthesis
Nakamura, Jun,Yamashiro, Hidenori,Miya, Hiroto,Nishiguchi, Kenzo,Maki, Hideki,Arimoto, Hirokazu
supporting information, p. 12104 - 12112 (2013/09/23)
Vancomycin-resistant Staphylococcus aureus (S. aureus) (VRSA) uses depsipeptide-containing modified cell-wall precursors for the biosynthesis of peptidoglycan. Transglycosylase is responsible for the polymerization of the peptidoglycan, and the penicillin-binding protein 2 (PBP2) plays a major role in the polymerization among several transglycosylases of wild-type S. aureus. However, it is unclear whether VRSA processes the depsipeptide-containing peptidoglycan precursor by using PBP2. Here, we describe the total synthesis of depsi-lipid I, a cell-wall precursor of VRSA. By using this chemistry, we prepared a depsi-lipid II analogue as substrate for a cell-free transglycosylation system. The reconstituted system revealed that the PBP2 of S. aureus is able to process a depsi-lipid II intermediate as efficiently as its normal substrate. Moreover, the system was successfully used to demonstrate the difference in the mode of action of the two antibiotics moenomycin and vancomycin. Copyright
Stereo- and regioselective synthesis of squalene tetraepoxide
Tong, Rongbiao,Boone, Matthew A.,McDonald, Frank E.
experimental part, p. 8407 - 8409 (2010/02/17)
(Chemical Equation Presented) Squalene tetraepoxide, a putative biosynthetic precursor to a variety of oxacyclic triterpenoid natural products, has been efficiently synthesized by anionic coupling of two farnesol-derived diepoxides, which have arisen from
Total syntheses of durgamone, nakorone, and abudinol B via biomimetic oxa- and carbacyclizations
Tong, Rongbiao,Valentine, Jason C.,McDonald, Frank E.,Cao, Rui,Fang, Xikui,Hardcastle, Kenneth I.
, p. 1050 - 1051 (2007/10/03)
The first biomimetic total syntheses of ent-nakorone, ent-durgamone, and ent-abudinol B were accomplished by combining features of tandem polyepoxide cyclization with biomimetic polyene cyclization. The present biomimetic synthesis route offers efficient
