155896-89-2

Upstream product

• 19488-49-4 methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 87470-70-0 S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 
• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 7216-73-1 methyl β-D-cellobioside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-39-0 benzyl bromide 
• 156038-69-6 methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 

Downstream Products

• 423719-29-3 methyl 2,3,6-tri-O-benzyl-4-O-methyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 155786-86-0 methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthetic Phosphoethanolamine Cellobiose Promotes Escherichia coli Biofilm Formation and Congo Red Binding

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.

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.

Crystal and molecular structure of methyl 4-O-methyl-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside

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.

Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl β-lactoside as ligands for the Ricinus communis lecitins

The synthesis of all possible monomethyl ethers of methyl β-lactoside (1) has been performed from 1 in a straightforward way, making use of the different reactivity of the hydroxyl groups in alkylation and stannylation reactions.In addition, the deoxyfluoro derivatives of 1 at positions, 6, 3',4',epi-4', and 6' have been prepared by reaction of the appropriate substrates with diethylaminosulfur trifluoride or tetrabutylammonium fluoride.Finally, the 6-deoxyiodo and 6'-bromodeoxy analogues of 1 have also been prepared.