32304-16-8Relevant academic research and scientific papers
Synthesis and NMR characterisation of novel highly cyclised polyprenoid hydrocarbons from sediments
Grosjean,Poinsot,Charrie-Duhaut,Tabuteau,Adam,Trendel,Schaeffer,Connan,Dessort,Albrecht
, p. 711 - 719 (2001)
We report here on the identification of two novel hexacyclic alkanes (C33 and C35) occurring in bitumen. The C35 compound 1 was identified by comparison with a standard obtained by synthesis involving a biomimetic proton-induced extensive cyclisation of an acyclic heptaprenoid. This cascade cyclisation allows the formation of eleven asymmetric centres present in the natural compound in only one step. The C33 analogue 2 was identified by NMR studies after isolation from the saturated hydrocarbon fraction of a bituminous rock. Both compounds are "orphan" molecular fossils of biological lipids of unknown origin formed by the extensive cyclisation of higher regular polyprenoids.
Synthesis and shift-reagent-assisted full NMR assignment of bacterial (: Z 8, e 2,ω)-undecaprenol
Lee, Mijoon,Hesek, Dusan,Zají?ek, Jaroslav,Fisher, Jed F.,Mobashery, Shahriar
, p. 12774 - 12777 (2017/12/06)
The repeating isoprene unit is a fundamental biosynthetic motif. The repetitive structure presents challenges both for synthesis and for structural characterization. In this synthesis of the (Z8,E2,ω)-undecaprenol of prokaryotic glycobiology, we exemplify solutions to these challenges. Allylation of sulfone-derived carbanions controlled the stereochemistry, and its proof-of-structure was secured by Eu(hfc)3 complexation to disperse the overlaid resonances of its 1H NMR spectrum.
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
, 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
supporting information; 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
Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics
Gampe, Christian M.,Tsukamoto, Hirokazu,Wang, Tsung-Shing Andrew,Walker, Suzanne,Kahne, Daniel
, p. 9771 - 9778 (2012/02/15)
We present a flexible, modular route to GlcNAc-MurNAc-oligosaccharides that can be readily converted into peptidoglycan (PG) fragments to serve as reagents for the study of bacterial enzymes that are targets for antibiotics. Demonstrating the utility of these synthetic PG substrates, we show that the tetrasaccharide substrate lipid IV (3), but not the disaccharide substrate lipid II (2), significantly increases the concentration of moenomycin A required to inhibit a prototypical PG-glycosyltransferase (PGT). These results imply that lipid IV and moenomycin A bind to the same site on the enzyme. We also show the moenomycin A inhibits the formation of elongated polysaccharide product but does not affect length distribution. We conclude that moenomycin A blocks PG-strand initiation rather than elongation or chain termination. Synthetic access to diphospholipid oligosaccharides will enable further studies of bacterial cell wall synthesis with the long-term goal of identifying novel antibiotics.
Solid-phase organic synthesis of polyisoprenoid alcohols with traceless sulfone linker
Chang, Yi-Fan,Liu, Chen-Yu,Guo, Chih-Wei,Wang, Yen-Chih,Fang, Jim-Min,Cheng, Wei-Chieh
experimental part, p. 7197 - 7203 (2009/05/09)
(Chemical Equation Presented) Solid-phase organic synthesis of polyprenols with a traceless sulfone linker is described. The polymerbound benezenesulfinate is first linked with the "tail" building blocks of isoprenyl chlorides via S-alkylation. With use of dimsyl anion as an appropriate base, the polymer-bound α-sulfonyl carbanion is generated and coupled with other "body" building blocks in an efficient manner. After repeated processes and a global palladium-catalyzed desulfonation with LiEt3BH as the reducing agent, the desired polyprenols with various chain lengths and geometrical configurations are obtained in 32-59% overall yields. The solid-phase synthesis offers the advantage in facile isolation of polyprenols without tedious operation or time-consuming purification.
A general stereocontrolled, convergent synthesis of oligoprenols that parallels the biosynthetic pathway
Radetich, Branko,Corey
, p. 2430 - 2431 (2007/10/03)
A solution is reported to the classic unsolved problem of stereoselective synthesis of all-E oligoprenols, such as E-farnesylfarnesol, by a cationic coupling analogous to the biosynthetic pathway. The simplicity and efficacy of the method, which is outlined in Scheme 1, are demonstrated by the synthesis of a series of all-E oligoprenols from C20 to C35 in uniformly excellent overall yield. The success of the approach is due not only to the highly E-stereoselective C-C coupling that forms the oligoprenyl chain but also to the development of efficient syntheses of allylic secondary silanes and E-oligoprenal acetals, and to a selective allylic demethoxylation reaction. Copyright
Isoprenoid derivatives and anti-ulcer agents containing the same
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, (2008/06/13)
Anti-ulcer agents containing isoprenoid derivatives are provided. The isoprenoid derivatives are represented by the formula: STR1 wherein: R represents a group of formula STR2 In the above formula, R1, R2 and R3 may be the
Stereospecific Synthesis of (Z,Z,Z,Z,Z,Z,Z,Z,E,E)-Undecaprenol (Bacterialprenol) using an all-cis-Diterpene Building Block
Sato, Kikumasa,Miyamoto, Osamu,Inoue, Seiichi,Matsuhashi, Yasusuke,Koyama, Shingo,Kaneko, Toshihiko
, p. 1761 - 1762 (2007/10/02)
Base-induced coupling of two monoterpene building blocks (6) and (7) followed by functional group transformations afforded an all-cis-diterpene building block (4), which was used to effect C20 homologation of (E,E)-farnesol and (Z,Z,Z,Z,E,E)-heptaprenol (
