73199-54-9Relevant academic research and scientific papers
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
, 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
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
BIOMIMETIC EPOXIDATION OF BIOLOGICALLY SIGNIFICANT NONCONJUGATED DIOLEFINS
Nali, Micaela,Rindone, Bruno,Tollari, Stefano,Valletta, Lorenzo
, p. 207 - 212 (2007/10/02)
Neryl ethers and geranyl ethers are regioselectively oxidised by tetraphenylporphyrinato manganese(III) acetate/NaClO under phase-transfer conditions in pH 7 buffer to give monoepoxides at the isopropylidene double bond.Also chlorinated products are formed.The subsequent epoxidation at the allylic double bond is less efficient than the electrophilic with a neryl ether, more efficient with a geranyl ether.Chlorination may be suppressed by adding pyridine to the reaction medium.This leads to a faster reaction.
SYNTHESIS OF THE SAN JOSE SCALE'S SEX PHEROMONE COMPONENT USING AN AVAILABLE NATURALLY OCCURRING STARTING MATERIAL
Novak, Lajos,Poppe, Laszlo,Kis-Tamas, Attila,Szantay, Csaba
, p. 17 - 24 (2007/10/02)
(Z)-3,7-Dimethyl-2,7-octadien-1-yl propanoate (1), a component of the San Jose scale (Quadraspidiotus perniciosus, Comstock) pheromone, was prepared by the multistage isomerisation of the C6 carbon-carbon double bond of the readily available compound, nerol (3).The synthesis was carried out via the epoxide by subsequent LiAlH4 ring cleavage and Hofmann-like mesylate elimination.
Sulphone-based Elimination Reactions in Synthesis. Part 1. Moenocinol
Kocienski, Philip,Todd, Michael
, p. 1777 - 1781 (2007/10/02)
The fluoride-induced elimination of a β-phenylsulphonylsilane and the reductive elimination of a β-oxysulphone are key olefin-forming reactions in a synthesis of moenocinol .
STEREOSELECTIVE SYNTHESIS OF A CISOID C10 ISOPRENOID BUILDING BLOCK AND SOME ALL-CIS-POLYPRENOLS
Sato, Kikumasa,Miyamoto, Osamu,Inoue, Seiichi,Furusawa, Fumio,Matsuhashi, Yasusuke
, p. 725 - 728 (2007/10/02)
As the key compound for the construction of cisoid terpenoids, (2Z,6Z)-8-benzyloxy-1-chloro-2,6-dimethylocta-2,6-diene was sinthesized stereoselectively via the Wittig reaction starting from nerol.The ten-carbon building block was coupled with prenyl or neryl p-tolyl sulfone to afford, after reductive desulfonylation, (Z,Z)-farnesol and (Z,Z,Z)-nerylnerol, respectively.
A Synthesis of Moenocinol
Kocienski, Philip J.
, p. 2037 - 2039 (2007/10/02)
The fluoride-induced elimination of a β-silyl sulfone and the reductive elimination of a β-acyloxy sulfone are key olefin-forming reactions in a new synthesis of moenocinol .
