108671-40-5

Upstream product

• 71692-91-6 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 51842-16-1 methyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 71692-91-6 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 51842-18-3 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 100-44-7 benzyl chloride 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

LYSOSOMAL-ENZYME TARGETING: THE PHOSPHORYLATION OF SYNTHETIC D-MANNOSYL SACCHARIDES BY UDP-N-ACETYLGLUCOSAMINE:LYSOSOMAL-ENZYME N-ACETYLGLUCOSAMINE-PHOSPHOTRANSFERASE FROM RAT-LIVER MICROSOMES AND FIBROBLASTS

Phosphorylation of the D-mannose residues of lysosomal-enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes.The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes.To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides.Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy.Of all the D-mannosyl saccharides tested, α-D-Man-(1->2)-α-D-Man-(1->OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.

PREPARATION OF α AND Β ANOMERS OF VARIOUS ISOMERIC METHYL O-D-GALACTOPYRANOSYL-D-GALACTOPYRANOSIDES. STANDARDS FOR INTERPRETATION OF 13C-N.M.R. SPECTRA OF D-GALACTOPYRANANS

The four isomer of methyl O-β-D-galactopyranosyl-β-D-galactopyranoside were prepared by condensation of 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl bromide with appropriate, partially O-substitued derivatives of methyl β-D-galactopyranoside.Reaction of 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose with the same acceptors, in the presence of mercuric bromide, led to the formation of α and β linkages.Thus, it was possible to assign 13C-n.m.r. resonances of α and β anomers of methyl O-D-galactopyranosyl-β-D-galactopyranosides.In terms of application of these shift values and those of related D-galactobioses to the structual analysis of D-galactopyranans by shift comparisons, some generalizations can be made.For β-D-galactopyranans, the resonances glycosyloxylated carbon atoms of methyl O-β-D-galactopyranosyl-β-D-galactopyranosides are sensitive to structure and appear to have typical values, whereas limited variation was observed with shift of C-1' signals.On the other hand, for assigning structures to D-galactopyranans containing α linkages, the C-1' shifts (at higher field) of methyl O-α-D-galactopyranosyl-β-D-galactopyranosidesc are sensitive to linkage position, whereas those of glycosyloxylated carbon atoms vary only a little.