111462-66-9

Upstream product

• 1192366-21-4 C₄₈H₄₇Cl₄NO₁₅ 
• 64-19-7 acetic acid 
• 63167-69-1 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 80264-86-4 methyl 6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,3-O-isopropylidene-α-D-mannopyranoside 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 10028-45-2 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 
• 147985-38-4 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 116142-80-4 methyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 80599-54-8 methyl 2,4-di-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 7772-87-4 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3459-18-5 4-nitrophenyl N-acetyl-β-D-glucosaminide 

Relevant academic research and scientific papers

Conformational flexibility and dynamics of two (1→6)-Linked disaccharides related to an oligosaccharide epitope expressed on malignant tumour cells

The conformational flexibility and dynamics of two (1→6)-linked disaccharides that are related to the action of the glycosyl transferase GnT-V have been investigated. NMR NOE and T-ROE spectroscopy experiments, conformation-dependent coupling constants an

Control of glycoprotein synthesis. Characterization of (1->4)-N-acetyl-β-D-glucosaminyltransferases acting on the α-D-(1->3)- and α-D-(1->6)-linked arms of N-linked oligosaccharides

Hen oviduct membranes contain at least three N-acetyl-β-D-glucosaminyltransferases (GlcNAc-T) that attach a βGlcNAc residue in (1-4)-linkage to a D-Manp residue of the N-linked oligosaccharide core, i.e., (1->4)-β-D-GlcNAc-T III which adds a "bisecting " GlcNAc group to form the β-D-GlcpNAc-(1->4)-β-D-Manp-(1->4)-D-GlcNAc moiety: (1->2)-β-D-GlcNAc-T IV which adds a GlcNAc group to the (1->3)-α-D-Man arm to form the β-D-GlcpNAc-(1->4)-2)>-α-D-Manp-(1->3)-β-D-Manp-(1->4)-D-GlcpNAc component; and (1->4)-β-D-GlcNAc-T VI which adds a GlcNAc group to the α-D-Manp residue of β-D-GlcpNAc-(1->6)-2)>-α-D-Manp-R to form β-D-GlcpNAc-(1->6)-4)>-2)>-α-D-Manp-R.We now report a novel (1->4)-β-D-GlcNAc-T activity (GlcNAc-T VI') in hen oviduct membranes that transfers GlcNAc to β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-β-D-Manp-R to form β-D-GlcpNAc-(1->4)-2)>-α-D-Manp-(1->6)-β-D-Manp-R.The structure of the enzyme product was confirmed by 1H NMR spectroscopy.FAB-mass spectrometry and methylation analysis.Previous work with GlcNAc-T IV was carried out with biantennary substrates; we now show that hen oviduct membrane GlcNAc-T IV can also transfer GlcNAc to monoantennary β-D-GlcpNAc-(1->2)-α-D-Manp-(1->3)-β-D-Manp-R to form β-D-GlcpNAc-(1->4)-2)>-α-D-Man-p-(1->3)-β-D-Manp-R.The findings that GlcNAc-T VI'and IV have similar kinetic characteristics and that hen oviduct membranes can convert methyl β-D-GlcpNAc-(1->2)-α-D-Manp to methyl β-D-GlcpNAc-(1->4)-2)>-α-D-Manp suggest that these two activities may be due to the same enzyme.The R-group of the β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-β-D-Manp (or Glcp)-R substrate has an important influence on GlcNAc-T VI'enzyme activity.When R is GlcNAc or βGlc-ally, the activity is drastically reduced.This may be due to conformational factors and may explain why hen oviduct membranes add a GlcNAc residue in (1->4)-β-linkage mainly to the (1->3)-α-D-Man arm of the bi-antennary substrate β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-2)-α-D-Manp-(1->3)>-β-D-Manp-R to form β-D-GlcpNAc-(1->2)-α-D-Manp-(1->6)-2)-4)>-α-D-Manp-(1->3)>-β-D-Manp-R.

Enzymic synthesis of HexNAc-containing disaccharide glycosides.

The following disaccharide glycosides were obtained from the appropriate donor and acceptor glycosides by employing glycosidases from the mollusc Chamelea gallina as catalysts: alpha-D-Galp-OMe (N-acetyl-alpha-D- galactosaminidase), beta-D-GalpNAc-(1----3)-beta-D-Galp-OMe, beta-D-GlcpNAc-(1----3)-beta-D-Galp-OMe, and beta-D-GlcpNAc-(1----6)-alpha-D-Manp-OMe (N-acetyl-beta-D-hexosaminidase). The regioselectivity of the N-acetyl-beta-D-hexosaminidase-catalysed reactions depended on the anomeric configuration of the acceptor. Thus, alpha-D-Galp-OMe gave beta-D-GlcpNAc- (1----6)-alpha-D-Galp-OMe almost exclusively, whereas beta-D-Galp-OMe gave beta-D-GlcpNAc-(1----3)-beta-D-Galp-OMe and beta-D-GlcpNAc-(1----6)-beta-D-Galp-OMe in almost equal amounts. The isolation of the products by chromatography was straightforward.

Enzymic synthesis of di- and tri-saccharide glycosides, using glycosidases and beta-D-galactoside 3-alpha-sialyl-transferase.

The following disaccharide glycosides were obtained in yields of 10-35% from the appropriate donor and acceptor glycosides by employing glycosidases as catalysts: alpha-D-Galp-(1----3)-alpha-D-GalpNAc-OEt (alpha-D-galactosidase), beta-D-Galp-(1----3)-alpha-D-GalpNAc-OEt and beta-D-Galp-(1----3)-beta-D-GalpNAc-OEtBr (beta-D-galactosidase), beta-D-GlcpNAc-(1----6)-beta-D-Galp-OMe and beta-D-GlcpNAc-(1----6)-alpha-D-Manp-OMe (beta-N-acetylglucosaminidase). With beta-D-GlcpNAc-OEtSiMe3 as the acceptor, beta-D-galactosidase gave beta-D-Galp-(1----3)-beta-D-GlcpNAc-OEtSiMe3 almost exclusively, whereas, with beta-D-GlcpNAc-OMe as the acceptor, beta-D-Galp-(1----3)-beta-D-GlcpNAc-OMe was formed in only slightly excess over teh analogous beta-(1----4)-linked glycoside. The use of beta-D-galactosidase and beta-D-galactoside 3-alpha-sialyltransferase in sequence provided a convenient route to the trisaccharide glycosides alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-alpha-D-GalpNAc-OEt, alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-beta-D-GalpNAc-OE tBr, and alpha-D-Neup5Ac-(2----3)-beta-D-Galp-(1----3)-beta-D-GlcpNAc-OMe.

SYNTHESIS OF p-NITROPHENYL 6-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-α-D-MANNOPYRANOSIDE

The reaction of p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside and 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)--2-oxazoline gave a crystalline, 6-O-substituted disaccharide derivative which, on de-isopropylidenation followed b

Synthesis of Di- and Tri-saccharides Having the Sequences n(1-->X)-α-D-Man in the Glycan of glycopeptides

Five model di- and tri-saccharides corresponding to the part structures of the glycan of glycopeptides were synthesized with regio- and stereo-control.They were as follows: methyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside, methyl 4-