172603-65-5

Upstream product

• 100-39-0 benzyl bromide 
• 172603-70-2 methyl 4-azido-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 
• 115196-83-3 methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 74-88-4 methyl iodide 

Downstream Products

• 172603-71-3 methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 
• 172603-70-2 methyl 4-azido-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 
• 178812-81-2 methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthetic glycoconjugates characterize the fine specificity of: Brucella A and M monoclonal antibodies

The dominant cell wall antigen of Brucella bacteria is the O-polysaccharide component of the smooth lipopolysaccharide. Infection by various Brucella biovars causes abortions and infertility in a wide range of domestic and wild animals and debilitating disease in humans. Diagnosis relies on the detection of antibodies to the A and M antigens expressed in the O-polysaccharide. This molecule is a homopolymer of the rare monosaccharide, 4-formamido-4,6-dideoxy-d-mannopyranose (Rha4NFo). The A epitope is created by a uniform α1,2 linked internal polymeric sequence capped by a distinct tetrasaccharide sequence defining the M antigen. Unique oligosaccharides only available by chemical synthesis and conjugated via reducing and non-reducing residues to bovine serum albumin have revealed the structural basis of the fine specificity that allows the discrimination of these closely related A and M epitopes. All three M specific monoclonal antibodies (mAbs) are inferred to possess groove type binding sites open at each end, and recognize an α1,3 linked Rha4NFo disaccharide as a part of a trisaccharide epitope, which in two mAbs includes the terminal Rha4NFo residue. The binding site of one of these antibodies is sufficiently large to engage up to six Rha4NFo residues and involves weak recognition of α1,2 linked Rha4NFo residues. The third mAb binds an internal trisaccharide epitope of the M tetrasaccharide. Two A specific mAbs also possess groove type binding sites that accommodate six and four α1,2 linked Rha4NFo residues.

Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa

Methyl 4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside.Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetranamido)-2-O-methyl-α-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa.The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group.The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae O:1; serotype Inaba.The crystal structure of methyl 4,6-dideoxy-2-O-methyl-4-trifluoroacetamido-α-D-mannopyranoside is also described.Keywords: O-Polysaccharide; Vibrio cholerae O:1, serotype Ogawa; α-D-Mannopyranoside, methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-teronamido)-2-O-methyl; Synthesis; Antigenic determinant