137792-62-2Relevant academic research and scientific papers
σ-Ferrier rearrangement of carbohydrate derived vinylcyclopropanes: a facile approach to oxepane analogs
Ganesh, Venkataraman,Kundu, Taraknath,Chandrasekaran, Srinivasan
, p. 7268 - 7282 (2014)
This article presents our work on the σ-Ferrier ring-expansion of carbohydrate derived vinylcyclopropanes (VCPs) under electrophilic conditions mediated by chloramine-T and a phase-transfer catalyst. The present work serves as the first example on the stu
MOLECULAR PROBES FOR ANALYSIS OF METABOLISM OF GLYCOLYSIS INHIBITORS PRODRUGS AND SYNTHESIS METHODS THEREFORE
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Page/Page column 12-13, (2020/03/05)
The present invention relates to compounds according to structure (I) whereby one of R1 to R3 is -OCOCD3 and the other two are either hydroxyl or OAc, their synthesis and their use in for the analysis of the metabolism of glycolysis inhibitors.
Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer
Miller, David C.,Choi, Gilbert J.,Orbe, Hudson S.,Knowles, Robert R.
supporting information, p. 13492 - 13495 (2015/11/09)
Here we report a ternary catalyst system for the intramolecular hydroamidation of unactivated olefins using simple N-aryl amide derivatives. Amide activation in these reactions occurs via concerted proton-coupled electron transfer (PCET) mediated by an excited state iridium complex and weak phosphate base to furnish a reactive amidyl radical that readily adds to pendant alkenes. A series of H-atom, electron, and proton transfer events with a thiophenol cocatalyst furnish the product and regenerate the active forms of the photocatalyst and base. Mechanistic studies indicate that the amide substrate can be selectively homolyzed via PCET in the presence of the thiophenol, despite a large difference in bond dissociation free energies between these functional groups.
Total synthesis of n-acetylglucosamine-1,6-anhydro-n- acetylmuramylpentapeptide and evaluation of its turnover by ampd from escherichia coli
Hesek, Dusan,Lee, Mijoon,Zhang, Weilie,Noll, Bruce C.,Mobashery, Shahriar
supporting information; experimental part, p. 5187 - 5193 (2009/09/30)
The bacterial cell wall is recycled extensively during the course of cell growth. The first recycling event involves the catalytic action of thelytic transglycosylase enzymes, which produce an uncommon 1,6-anhydropy ranose moiety during separation of the muramyl residues from the peptidoglycan, the major constituent of the cell wall. This product, an N-acetyl-β-D-glucosamine- (1→4)-1,6-anhydro-N-acetyl-β-Dmuramylpeptide, is either internalized to initiate the recycling process or diffuses into the milieu to cause stimulation of the pro-inflammatory responses by the host. We report the total syntheses of N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-meso-DAP-D-Ala-D-Ala (compound 1, the product of lytic transglycosylase action on the cell wall of Gram-negative bacteria) and N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-L-Lys-D-Ala-D-Ala (compound 2, from lytic transglycosylase action on the cell wall of Gram-positive bacteria). The syntheses were accomplished in 15 linear steps. Compound 1 is shown to be a substrate of the AmpD enzyme of the Gram-negative bacterium Escherichia coli, anenzyme that removes the peptide from the disaccharide scaffold in the e arly cytoplasmic phase of cell wall turnover.
Adducts of uridine and glycals as potential substrates for glycosyltransferases
Wandzik, Ilona,Bieg, Tadeusz
, p. 401 - 416 (2008/03/13)
We report on the synthesis of 2-deoxyglycosyl derivatives of uridine as potential donor substrates for glycosyltransferases. The totally stereoselective synthesis is accomplished by two sequential addition reactions of uridine derivatives to glycals promo
A new procedure for the preparation of β-keto-δ-lactones from sugars and their transformation into glycosyl acceptors in disaccharides synthesis
Bartolozzi, Alessandra,Capozzi, Giuseppe,Menichetti, Stefano,Nativi, Cristina
, p. 251 - 253 (2007/10/03)
(matrix presented) Glycals are effective starting materials for the synthesis of enantiopure β-ketone-δ-lactones. They are easily transformed, through a two-step, one-pot reaction, into the corresponding α,α′-dioxothiones which in turn can be quantitative
Radical Cyclization Routes to Bridged Pyranosides as Precursors of Densely Functionalized Cycloalkanes
Alonso, R. A.,Vite, G. D.,McDevitt, R. E.,Fraser-Reid, B.
, p. 573 - 584 (2007/10/02)
Glycals derived from hexapyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group.Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on
