566934-68-7

Upstream product

• 4547-43-7 methyl 6-hydroxycaproate 
• 115234-11-2 ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 
• 117107-69-4 1,2-Di-O-acetyl-4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 566934-69-8 5-methoxycarbonylpentyl 2-O-acetyl-4-amino-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 848828-27-3 5-(methoxycarbonyl)pentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 848828-29-5 5-(methoxycarbonyl)pentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 848828-28-4 5-(methoxycarbonyl)pentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 848828-31-9 5-methoxycarbonylpentyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 848828-30-8 5-methoxycarbonylpentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl(1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl (1→2) 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 
• 566934-70-1 5-methoxycarbonylpentyl 2-O-acetyl-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside 

Relevant academic research and scientific papers

Immunogens from a synthetic hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype Ogawa

The known 5-(methoxycarbonyl)pentyl α-glycoside of the hexasaccharide of Vibrio cholerae O:1, serotype Ogawa 24 was newly prepared. The efficiency of construction of the hexasaccharide from the disaccharide glycosyl acceptor 6 and each of the two tetrasaccharide glycosyl donors 16, and 18, as an alternative to the iterative coupling of the disaccharide glycosyl donor 7 with 6, was evaluated. Compound 24 was treated with each of hydrazine hydrate, ethylenediamine, and hexamethylenediamine to give ligands 25, 27, and 29, respectively, equipped with different linkers. Reaction of the foregoing compounds with squaric acid diethyl ester, and the reactions of the thus formed monoesters 26, 28, and 30 with BSA were evaluated. The rate of formation of the corresponding monoester was higher with hydrazide 25 than with amines 27 and 29, whose reaction rates were virtually the same. Reactions of squaric acid derivatives 26, 28, and 30 with BSA were conducted under the same conditions (reaction temperature, ligand-BSA ratio, and concentration with respect to the hapten) and targeted for neoglycoconjugates with 24-BSA ratio of ～5. Monitoring the conversions by SELDI-TOF mass spectrometry in conjunction with the ProteinChip system made it possible to conduct the conjugations in controlled fashion, and to terminate the reactions when the desired carbohydrate-protein ratios were reached. Products from 26, 28, and 30, neoglycoconjugates 31-33, containing 4.9, 5.0, and 5.1 moles of 24/BSA, respectively, were obtained in 87-93% yields. When the conjugation started with the initial molar carbohydrate-protein ratio of 15:1, the final molar carbohydrate-BSA ratio reached after 14 days with ligands 26, 28, and 30 was 9.0, 11.0, and 9.1, respectively.

Neoglycoconjugates from synthetic tetra- and hexasaccharides that mimic the terminus of the O-PS of Vibrio cholerae O:1, serotype Inaba

A glycosyl acceptor and a glycosyl donor having the N-3-deoxy-L-glycero-tetronic acid side chain already attached have been prepared and used for the synthesis of the di- through to the hexasaccharide that mimic the upstream terminus of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Inaba. The target tetra- and the hexasaccharide, which were obtained in the form of 5-methoxycarbonylpentyl glycosides, were linked to BSA using squaric acid diester chemistry. The conjugation reactions were monitored by surface enhanced laser desorption ionization-time of flight mass spectrometry (SELDI-TOF MS). This allowed the progression of the conjugation of the synthetic oligosaccharides in a controlled way and termination of the reaction when the desired molar hapten/BSA ratio had been reached, yielding neoglycoconjugates with predetermined carbohydrate/carrier ratios. The ability to monitor the conjugation by the SELDI-TOF MS technique made it possible to prepare, from one hapten in a one-pot reaction, several neoglycoconjugates having different, predetermined carbohydrate/carrier ratios.