52188-74-6Relevant 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
Synthesis and NMR characterization of (Z, Z, Z, Z, E, E,ω)- heptaprenol
Hesek, Dusan,Lee, Mijoon,Zajicek, Jaroslav,Fisher, Jed F.,Mobashery, Shahriar
experimental part, p. 13881 - 13888 (2012/10/08)
We describe a practical, multigram synthesis of (2Z,6Z,10Z,14Z,18E,22E)-3, 7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosaheptaen-1-ol [(Z 4,E2,ω)-heptaprenol, 4] using the nerol-derived sulfone 8 as the key intermediate. Su
Selenium dioxide E-methyl oxidation of suitably protected geranyl derivatives - Synthesis of farnesyl mimics
Fairlamb, Ian J.S.,Dickinson, Julia M.,Pegg, Mathew
, p. 2205 - 2208 (2007/10/03)
Difunctional allylic terpenes are important synthetic building blocks. Functionalisation of protected geranyl derivatives by SeO2 provides a convenient route to such compounds. The effect of the geranyl protecting group on the oxidation of the
Regio- and Stereo-selective Oxidation of gem-Dimethyl Olefins via -Sigmatropic Rearrangement of Allyl Amine Oxides
Inoue, Seiichi,Iwase, Norimichi,Miyamoto, Osamu,Sato, Kikumasa
, p. 2035 - 2038 (2007/10/02)
Highly regio- and stereo-selective oxidation sequences are described for the efficient conversion of the gem-dimethyl olefin terminus of acyclic terpenes to terminal trans-allylic alcohols and trans α,β-unsaturated aldehydes.
FACILE SYNTHESIS OF (E)-ALLYLIC ALCOHOLS BY ACID-CATALYZED MODIFICATION OF THE MISLOW-EVANS REARRANGEMENT OF ALLYLIC SULFOXIDES
Masaki, Yukio,Sakuma, Kazuhiko,Kaji, Kenji
, p. 2531 - 2534 (2007/10/02)
The Mislow-Evans rearrangement of α,β- and α,γ-disubstituted allylic sulfoxides (2) to (E)-allylic alcohols (4) was found to occur under acidic conditions.By combination of this method with a catalytic oxidation of allylic sulfides (1), a novel one-pot tr
FACILE FUNCTIONALIZATION OF THE ISOPROPYLIDENE TERMINUS OF ACYCLIC MONOTERPENES BY WAY OF BENZENESULFENYL CHLORIDE ADDITION
Masaki, Yukio,Hashimoto, Kinji,Kaji, Kenji
, p. 3481 - 3490 (2007/10/02)
Highly site- and regioselective terminal functionalizations of acyclic monoterpenes 1 via benzenesulfenyl chloride addition followed by hydrolysis assisted by silica gel, dehydrochlorination under neutral or weakly basic condition, or dehydrochlorination by strongly basic treatment respectively providing β-hydroxy sulfides 3, terminal methallylic sulfides 4, or vinylsulfides 5 are developed.Conversion of 4 to terminal trans-allylic alcohols 10 via sulfoxides 9 by the Evans procedure is also described.
Facile Regio- and Stereo-specific Allylic Oxidation of gem-Dimethyl Olefins via Addition of Benzenesulphenyl Chloride. Synthesis of Allylic Oxygenated Terpenes
Masaki, Yukio,Hashimoto, Kinji,Sakuma, Kazuhiko,Kaji,Kenji
, p. 1289 - 1295 (2007/10/02)
Novel and facile terminal trans-allylic and internal allylic oxidations of the gem-dimethyl olefin terminus of the terpenoids (1) are described which take place site-, regio-, and stereo-specificially via the same intermediate adduct between benzenesulphenyl chloride and (1).By this method, the allylic oxygenated terpenes (+/-)-nuciferal (11), (+/-)-ar-turmerone (12), (+/-)-ipsdienol (3c), neotorreyol (2e), (+/-)-6-hydroxydendrolasin (3e), and 6-oxodendrolasin (14) were synthesized.
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.
Synthese von Lycopin
Hofer, Arnold,Eugster, Conrad Hans
, p. 365 - 370 (2007/10/02)
Synthesis of Lycopene; Lycopene having at both ends the deuteriated methyl groups trans to the chain has been synthesized for further biochemical experiments aimed to elucidate the stereochemistry of the cyclization step.Incident
