75669-79-3

Basic information

• Product Name: Methyl 2-Acetamido-2-Deoxy-3-O-(b-D-Galactopyranosyl)- a-D-Galactopyranoside
• Synonyms: Gal1-β-3GalNAc1-α-OMe;Methyl 2-Acetamido-2-Deoxy-3-O-(b-D-Galactopyranosyl)- α-D-Galactopyranoside;Gal1-b-3GalNAc1-α-OMe
• CAS NO: 75669-79-3
• Molecular Formula: C15H27NO11
• Molecular Weight: 397.374
• Product Categories: Oligosaccharide Compounds;Oligosaccharides
• Mol File: 75669-79-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 270-272°C dec.
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: Methyl 2-Acetamido-2-Deoxy-3-O-(b-D-Galactopyranosyl)- a-D-Galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-Acetamido-2-Deoxy-3-O-(b-D-Galactopyranosyl)- a-D-Galactopyranoside(75669-79-3)
• EPA Substance Registry System: Methyl 2-Acetamido-2-Deoxy-3-O-(b-D-Galactopyranosyl)- a-D-Galactopyranoside(75669-79-3)

Safety Data

• Hazardous Substances Data: 75669-79-3(Hazardous Substances Data)

Usage

Chemical Properties

White Granular Crystalline Solid

Uses

Different sources of media describe the Uses of 75669-79-3 differently. You can refer to the following data:
1. A substrate for 2,3-O-Sialyltransferase. A synthetic derivative of T antigen, a tumor associated disaccharide
2. A substrate for 2,3-O-Sialyltransferase. A synthetic derivative of T antigen, a tumor associated disaccharide.

Upstream product

• 6082-22-0 methyl α-D-N-acetylgalactosamine 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 6748-94-3 methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 6619-04-1 N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 139869-58-2 Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-glucopyranoside 
• 139760-21-7 Methyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-3-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 139894-28-3 methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 139760-22-8 Methyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 139760-20-6 Methyl 2-acetamido-2-deoxy-3-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 4291-68-3 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 
• 173314-50-6 methyl O-<3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl>-(1<*>3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 139760-24-0 Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 139760-23-9 Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Relevant articles and documents

Escherichia coli O86 O-antigen biosynthetic gene cluster and stepwise enzymatic synthesis of human blood group B antigen tetrasaccharide

Previous study showed that some Gram-negative bacteria possess human blood group activity. Among them, Escherichia coli O86 has high blood group B activity and weak blood group A activity. This is due to the cell surface O-antigen structure, which resembles that of human blood group B antigen. In this study, we sequenced the entire E. coli O86 antigen gene cluster and identified all the genes responsible for O-antigen biosynthesis by sequence comparative analysis. The blood group B-like antigen in E. coli O86 O-polysaccharide was synthesized by sequentially employing three glycosyltransferases identified in the gene cluster. More importantly, we identified a new bacterial glycosyltransferase (WbnI) equivalent to human blood group transferase B (GTB). The enzyme substrate specificity and stepwise enzymatic synthesis of blood group B-like antigen revealed that the biosynthetic pathway of B antigen is essentially the same in E. coli O86 as in humans. This new finding provides a model to study the specificity and structure relationship of blood group transferases and supports the hypothesis of anti-blood group antibody production by bacterial stimulation. Copyright

Selective anomeric acetylation of unprotected sugars in water

High yielding selective acetylation of only the anomeric hydroxyl of unprotected sugars is possible in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), thioacetic acid, and a suitable base. The reaction, which may be performed on a multi-gram scale, is stereoselective for sugars that possess a hydroxyl group at position-2, exclusively yielding the 1,2-trans products. The use of an iterative reagent addition procedure allows the use of sodium carbonate as the base, avoiding the formation of triethylammonium salts, which may hamper product purification. The glycosyl acetate products may be used as donor substrates for glycosidase-catalysed synthesis. The crude aqueous acetylation reaction mixture may also be used for this purpose.

Synthesis and conformational analysis of the T-antigen disaccharide (β-D-Gal-(1←3)-α-D-GalNAc-OMe)

We report an improved synthesis of the T-antigen disaccharide [β-D-Gal-(1←3)-α-D-GalNAc-OMe], incorporating recycling of the undesired β-glycosyl acceptor [methyl 2-azido-4,6-benzylidene-2-deoxy-β-D-galactopyranoside (9β)] through anomerization by treatment with FeCl3. The conformational analysis of the disaccharide made use of high quality NOE data in combination with extensive Metropolis Monte-Carlo (MMC) and molecular dynamic (MD) simulations. To sample the conformational space sufficiently, 9.5·106 Monte-Carlo steps were collected for the MMC simulations, while the fully solvated MD simulations were performed for 10 ns for comparison. In general, the MMC and MD simulations agreed very well. Comparison of theoretical NOE curves from both MMC and MD simulations with the experimental curves showed that the disaccharide populates two regions of conformational space, with a population of about 95% for the global minimum energy region and about 5% for a local minimum energy region.