197663-19-7

Upstream product

• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 68733-26-6 2-deoxy-2-azidogalactopyranose 
• 108-98-5 thiophenol 
• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 

Downstream Products

• 914800-95-6 phenyl 2-azido-2-deoxy-1-thio-6-O-trityl-D-galactopyranoside 
• 1441128-53-5 2-(trimethylsilyl)ethyl (2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2,-trichloroethoxycarbonylamino)-β-D-galactopyranoside 
• 1381864-49-8 2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranose 
• 849033-16-5 phenyl 1-thio-2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranoside 
• 1226524-10-2 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactoside 
• 1400562-36-8 phenyl 2-azido-6-O-benzyl-3,4-di-O-chloroacetyl-2-deoxy-1-thio-β-D-galactopyranoside 
• 1400562-34-6 phenyl 2-azido-6-O-benzyl-3,4-di-O-chloroacetyl-2-deoxy-1-thio-α-D-galactopyranoside 
• 675876-42-3 (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 370554-13-5 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 1356031-22-5 phenyl 4-O-(2-azido-4-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-galactopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside 
• 1372074-05-9 phenyl 4-O-(2-azido-3-O-benzoyl-4-phthalimido-2,4,6-trideoxy-α-D-galactopyranosyl)-2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

In vitro synthesis of mucin-type O-glycans using saccharide primers comprising GalNAc-Ser and GalNAc-Thr residues

Mucin-type O-glycosylation of serine or threonine residue in proteins is known to be one of the major post-translational modifications. In this study, two novel alkyl glycosides, Nα-lauryl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serineamide (GalNAc-Ser-C12) and Nα-lauryl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonineamide (GalNAc-Thr-C12) were synthesized as saccharide primers to prime mucin-type O-glycan biosynthesis in cells. Upon incubating human gastric cancer MKN45 cells with the saccharide primers, 22 glycosylated products were obtained, and their structures were analyzed using liquid chromatography-mass spectrometry and enzyme digestion. The amounts of glycosylated products were dependent on the amino acid residues in the saccharide primers. For example, in vitro synthesis of T antigen (Galβ1-3GalNAc), fucosyl-T (Fucα1-2Galβ1-3GalNAc), and sialyl-T (NeuAcα2-3Galβ1-3GalNAc) preferred a serine residue, whereas sialyl-Tn (NeuAcα2-6GalNAc) preferred a threonine residue. Furthermore, the glycosylated products derived from GalNAc-Ser/Thr-C12 and Gal-GalNAc-Ser/Thr-C12 using cell-free synthesis showed the same amino acid selectivity as those in the cell experiments. These results indicate that glycosyltransferases involved in the biosynthesis of mucin-type O-glycans distinguish amino acid residues conjugated to GalNAc. The saccharide primers developed in this study might be useful for comparing mucin-type oligosaccharides in cells and constructing oligosaccharide libraries to study cell function.

Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant

The α-aminooxy derivative of the Thomsen-Friedenriech tumor associated carbohydrate antigen has been synthesized in 11 steps utilizing a d-GalN3 acceptor carrying a pre-installed α-N- hydroxysuccinimidyl moiety. The natural α linkage was prepar

Synthesis and biological evaluation of the Forssman antigen pentasaccharide and derivatives by a one-pot glycosylation procedure

The synthesis and biological evaluation of the Forssman antigen pentasaccharide and derivatives thereof by using a one-pot glycosylation and polymer-assisted deprotection is described. The Forssman antigen pentasaccharide, composed of GalNAcα(1,3)GalNAcβ(

An improved method for the synthesis of protected glycosyl fluorides from thioglycosides using N,N-diethylaminosulfur trifluoride (DAST)

The direct conversion of thioglycosides to glycosyl fluorides frequently used in oligosaccharide synthesis was examined using N,N-diethylaminosulfur trifluoride (DAST). Although the reaction proceeded without N-bromosuccinimide (NBS), in some cases it was found that the electrophilicity of the Vilsmeier-type electrophilic sulfinium cation species was not sufficient for the activation of certain less-reactive thioglycosides. Here, we report the results of fluorination reactions of a series of monosaccharides using DAST in the absence of NBS, and also discuss the acceleration of the reaction in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) resulting in excellent product yields.

Synthesis of the repeating unit of the lipoteichoic acid of Streptococcus pneumoniae

The lipoteichoic acid repeating unit of Streptococcus pneumoniae is a complex pseudopentasaccharide (3). It consists of one ribitol-phosphate, one 2-acetamino-4-amino-2,4,6-trideoxy-galactose, one glucose and two galactosamine residues each differently li

Total synthesis of lipoteichoic acid of streptococcus pneumoniae

"Chemical Equation Preseted" Mixed signals: The glycophospholipid 1, consisting of two cholinylphosphoCalNAc units, two 2-acetamino-4-amino2,4,6- trideoxygalactose rings, three glucose residues each with different linkages to other sugar units, and a ribitolphosphate residue, has been synthesized. Target 1 is recognized by the immune system, but not by the TLR-2 signaling receptor as previously postulated.

Synthesis of Tn, and sialyl Tn antigen-lipid a analog conjugates for synthetic vaccines

Conjugates of Tn and sialyl Tn antigen with N-teradecanoyl L-seryl-β- alanine-containing 9-glucosamine derivatives structurally related to lipid A as a immunoadjuvant were synthesized for the development of totally synthetic vaccines against cancers or HIV.