117107-69-4

Upstream product

• 108-24-7 acetic anhydride 
• 115196-83-3 methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 20881-80-5 (2S,3S,4S,5S,6R)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3,4-diol 
• 100-39-0 benzyl bromide 
• 22932-34-9 methyl 6-deoxy-6-iodo-2,3-O-isopropylidene-α-D-mannopyranoside 
• 115479-46-4 methyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 15830-63-4 methyl 6-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranosid-4-ulose 
• 104846-19-7 methyl 6-deoxy-2,3-O-isopropylidene-α-D-talopyranoside 
• 115479-44-2 methyl 6-deoxy-2,3-O-isopropylidene-4-O-trifluoromethanesulfonyl-α-D-talopyranoside 
• 115196-82-2 methyl 2-O-acetyl-4-azido-4,6-dideoxy-α-D-mannopyranoside 
• 115479-45-3 methyl 4-azido-4,6-dideoxy-2,3-O-isopropylidene-α-D-mannopyranoside 

Downstream Products

• 115234-11-2 ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 
• 121804-01-1 Ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside 
• 219838-65-0 4-(1,3-dioxolan-2-yl)-3-oxabutyl 4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranoside 
• 219838-63-8 4-(1,3-dioxolan-2-yl)-3-oxabutyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 219838-56-9 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl trichloroacetimidate 
• 219838-85-4 Acetic acid (2S,3S,4S,5R,6R)-5-amino-4-benzyloxy-2-[2-([1,3]dioxolan-2-ylmethoxy)-ethoxy]-6-methyl-tetrahydro-pyran-3-yl ester 
• 219838-60-5 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 219838-74-1 4-(1,3-dioxolan-2-yl)-3-oxabutyl 3-O-benzyl-2-O-methyl-4,6-dideoxy-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-α-D-mannopyranoside 
• 219838-72-9 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-acetyl-3-O-benzyl-4,6-dideoxy-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-α-D-mannopyranoside 
• 219838-70-7 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(4-azido-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 219838-68-3 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 219838-76-3 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-<4-(2,4-di-O-acetyl-3-deoxy-L-glycerotetronyl)-3-O-benzyl-2-O-methyl-4,6-dideoxy-α-D-mannopyranosyl>-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 219838-75-2 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-<2-O-acetyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl>-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 115196-92-4 methyl O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyran... 

Relevant academic research and scientific papers

SYNTHESIS OF ANTIGENIC DETERMINANTS OF THE Brucella A ANTIGEN, UTILIZING METHYL 4-AZIDO-4,6-DIDEOXY-α-D-MANNOPYRANOSIDE EFFICIENTLY DERIVED FROM D-MANNOSE

A strategy for the synthesis of Brucella O-antigenic determinants containing 2-linked 4,6-dideoxy-4-formamido-α-D-mannopyranosyl residues is described.The approach adopted also permits the N-acyl moiety to be varied.A high-yield synthesis of methyl 4-azid

POLYSACCHARIDE AND METHODS

There is provided a molecule comprising a chain of seven or more contiguous units of 4,6-dideoxy-4-acylamido-α-pyranose, each pair of units joined by a C1-C2 or a C1-C3 link, the chain having a terminal end and a reducing end, wherein the pyranose ring in the unit of the chain most distal from the reducing end is linked to a cap structure. The cap structure is not a 4,6-dideoxy-4-acylamido-α-pyranose. There are also provided vaccine compositions comprising the molecule and methods of vaccinating an animal against infection by a Brucella organism, including methods of distinguishing between a vaccinated and an infected animal. There are further provided novel methods of detecting the presence in a sample of an anti-Brucella antibody.

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.

Design and synthesis of a universal antigen to detect brucellosis

Upgrading diagnostics: A universal antigen has been prepared for the detection of brucellosis caused by any Brucella species that express a smooth lipopolysaccharide. This nonasaccharide, which encompasses Brucella A- and M-antigenic determinants, is uniquely available only by chemical synthesis. Copyright

Synthesis of four glycosides of a disaccharide fragment representing the terminus of the O-polysaccharide of Vibrio cholerae O:1, serotype Inaba, bearing aglycons suitable for linking to proteins

Methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside was converted into the crystalline 2-(trimethylsilyl)ethyl 4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside. Debenzoylation of the latter, followed by glycosylation of the resulting 2-hydroxy derivative with 2-O-acetyl-4-azido-4,6-dideoxy-α-D-mannopyranosyl chloride, gave the 2-(trimethylsilyl)ethyl glycoside of the corresponding disaccharide (8). Deacetylation of 8, followed by reduction of the resulting 4-azido-2-hydroxy derivative with H2S, gave the corresponding amine 10. The latter was treated with 4-O-benzyl-3-deoxy-L-glycero-tetronic acid to give, after debenzylation and acetylation, the fully protected 2-(trimethylsilyl)ethyl α-glycoside of the disaccharide fragment of the O-PS of Vibrio cholerae O:1, serotype Inaba (13). Compound 13 was transformed into the corresponding 1-trichloroacetimidate which was treated, separately, with methyl 6-hydroxyhexanoate and 2-(2-methoxycarbonylethylthio)ethanol, to give two analogs of 13 possessing a differing linkage arm, namely the methyl esters 16 and 17. Each of 16 and 17 was treated with aqueous sodium hydroxide, followed by a cation-exchange resin, to give the two corresponding carboxylic acids (19 and 22). Alternately, treatment of 16 and 17 with hydrazine hydrate gave the acid hydrazides 20 and 23.

SYNTHESIS OF THE METHYL α-GLYCOSIDE OF THE INTRACATENARY DISACCHARIDE REPEATING UNIT OF THE O-POLYSACCHARIDE OF VIBRIO CHOLERAE O:1. A COMPARISON OF TWO ASSEMBLY STRATEGIES

The two strategies engaged in the construction of the title disaccharide 17 comprise: 1. assembly of a diamino disaccharide and its N-acylation using chiral reagents to introduce the 4-(3-deoxy-L-glycero-tetronyl) group, followed by deprotection, and 2. preparation of a glycosyl acceptor and a glycosyl donor both having the chiral 3-deoxy-L-glycero-tetronamido group already in place, their condensation to give a fully substituted disaccharide, and deprotection.Accordingly, the crystalline diamino disaccharide methyl 2-O-(4-amino-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-4-amino-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside, (14), was prepared from the known diazido disaccharide 12, and treated with the lactone 30, or its acetylated or benzylated analogs 31 and 32, respectively, as the N-acylating reagents.Subsequent deprotection of the respective products applying standard chemistry gave 17.Alternatively, the methyl α-glycoside of the monomeric intracatenary repeating unit of Vibrio cholerae O:1 (2) was converted to the fully benzoylated glycosyl chloride 26, and the latter glycosyl donor was condensed with methyl 3-O-benzyl-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-α-D-mannopyranoside (24), to give the corresponding, fully protected derivative 27.Deprotection then readily gave 17.It appears that the title disaccharide can be most efficiently synthesized using synthons 24 and 26.The lactones 30 and 32 appear to be promising acylating reagents for the introduction of the 3-deoxy-L-glycero-tetronamido group when higher oligosaccharides in this series will be synthesized via their (poly)amino precursors.