156038-69-6Relevant academic research and scientific papers
Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2
Mukherjee, Mana Mohan,Basu, Nabamita,Chaudhury, Aritra,Ghosh, Rina
, p. 109301 - 109314 (2016)
A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.
Synthetic Phosphoethanolamine Cellobiose Promotes Escherichia coli Biofilm Formation and Congo Red Binding
Nguyen, Johny M.,Moore, Rebecca E.,Spicer, Sabrina K.,Gaddy, Jennifer A.,Townsend, Steven D.
, p. 2540 - 2545 (2021/05/10)
Urinary tract infections (UTIs) are caused by bacteria growing in complex, multicellular enclosed aggregates known as biofilms. Recently, a zwitterionic cellulose derivative produced in Escherichia coli (E. coli) was determined to play an important role in the formation and assembly of biofilms. In order to produce a minimal, yet structurally defined tool compound to probe the biology of the naturally occurring polymer, we have synthesized a zwitterionic phosphoethanolamine cellobiose (pEtN cellobiose) and evaluated its biofilm activity in the Gram-negative bacterium E. coli, a pathogen implicated in the pathogenesis of UTIs. The impact of synthetic pEtN cellobiose on biofilm formation was examined via colorimetric assays which revealed an increase in cellular adhesion to an abiotic substrate compared to untreated samples. Additionally, Congo red binding assays indicate that culturing E. coli in the presence of pEtN cellobiose enhances Congo Red binding to bacterial cells. These results reveal new opportunities to study the impact glycopolymers have on cellular adhesion in Gram-negative pathogens.
Some approaches to glycosylated versions of methyl β-acarviosin
Fairweather, Jon K.,McDonough, Matthew J.,Stick, Robert V.,Tilbrook, D. Matthew G.
, p. 197 - 205 (2007/10/03)
In a first approach to a glycosylated version of 'methyl β-acarviosin', a putative inhibitor of cellulases, cellobiose was converted into a carbocyclic enone that could not be transformed into the required amine for a subsequent alkylation. Alternatively,
Crystal and molecular structure of methyl 4-O-methyl-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside
Mackie, Iain D.,Roehrling, Juergen,Gould, Robert O.,Pauli, Jutta,Jaeger, Christian,Walkinshaw, Malcolm,Potthast, Antje,Rosenau, Thomas,Kosma, Paul
, p. 161 - 166 (2007/10/03)
The cellulose model compound methyl 4-O-methyl-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (6) was synthesised in high overall yield from methyl β-D-cellobioside. The compound was crystallised from methanol to give colourless prisms, and the crystal structure was determined. The monoclinic space group is P21 with Z = 2 and unit cell parameters a = 6.6060 (13), b = 14.074 (3), c = 9.3180 (19) A, β = 108.95(3)°. The structure was solved by direct methods and refined to R = 0.0286 for 2528 reflections. Both glucopyranoses occur in the 4C1 chair conformation with endocyclic bond angles in the range of standard values. The relative orientation of both units described by the interglycosidic torsional angles [φ (O-5′-C-1′-O-4-C-4) -89.1°, φ (C-1′-O-4-C-4-C-5) -152.0°] is responsible for the very flat shape of the molecule and is similar to those found in other cellodextrins. Different rotamers at the exocyclic hydroxymethyl group for both units are present. The hydroxymethyl group of the terminal glucose moiety displays a gauche-trans orientation, whereas the side chain of the reducing unit occurs in a gauche-gauche conformation. The solid state 13C NMR spectrum of compound 6 exhibits all 14 carbon resonances. By using different cross polarisation times, the resonances of the two methyl groups and C-6 carbons can easily be distinguished. Distinct differences of the C-1 and C-4 chemical shifts in the solid and liquid states are found.
