58871-11-7Relevant articles and documents
NOVEL ACETATES OF 2-DEOXY MONOSACCHARIDES WITH ANTICANCER ACTIVITY
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Paragraph 0114; 0115; 0116; 0122, (2017/04/01)
Novel compounds and methods of using the same to inhibit glycolysis and treat cancer and other diseases are provided herein.
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.
Totally Stereoselective Synthesis of 1,3-Disaccharides through Diels-Alder Reactions
Bartolozzi, Alessandra,Pacciani, Stefania,Benvenuti, Cecilia,Cacciarini, Martina,Liguori, Francesca,Menichetti, Stefano,Nativi, Cristina
, p. 8529 - 8533 (2007/10/03)
A nonclassical, totally stereoselective synthesis of orthogonally protected 1,3-disaccharides is reported. Enantiomerically pure β-keto-δ-lactones, efficiently obtained from glucal and galactal, are transformed into electron-poor heterodienes and chemo-,
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
