1448622-61-4

Upstream product

• 1403362-13-9 methyl (N-benzylbenzyloxycarbonyl-5-aminopentyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate 
• 1448614-11-6 C₄₃H₅₁NO₁₄Se 
• 85382-90-7 methyl-4,5,7,8-tetra-O-acetyl-2,6-anhydro-2,3-dideoxy-D-manno-oct-2-enosonat 
• 920958-49-2 benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

TOTAL SYNTHESIS AND IMMUNOLOGICAL EVALUATION OF SACCHARIDE MOIETIES OF THE LIPOPOLYSACCHARIDE FROM NEISSERIA MENINGITIDIS

The present invention relates to the total chemical synthesis of the monosaccharide 35# (R' = H), the disaccharide 36# (R' ≠ H; R'' = H), the trisaccharide 37# (R' ≠ H; R'' ≠ H; R''' = H) and the tetrasaccharide 1#(R' ≠ H; R'' ≠ H; R''' ≠ H) of the following general formula wherein R represents –Y–NH2 Y represents a linker R' is H or R'' is H or R''' is H or of the lipopolysaccharide from Neisseria meningitidis, as well as to the trisaccharide 37# and the tetrasaccharide 1#, to vaccines containing at least one of the saccharides 1#, 35#, 36#, and 37# and to the use of such vaccine for immunization against diseases caused by infection with bacteria containing the tetrasaccharide α-GlcNAc-(1→2)-α- Hep-(1→3)-α-Hep-(1→5)-α-Kdo or the trisaccharide α-Hep-(1→3)-α-Hep-(1→5)-α- Kdo or α-GlcNAc-(1→2)-α-Hep-(1→3)-α-Hep, especially for immunization against meningitis, septicaemia, pneumonia and nasopharyngitis caused by Neisseria meningitidis.

Diversity-oriented synthesis of inner core oligosaccharides of the lipopolysaccharide of pathogenic gram-negative bacteria

Lipopolysaccharide (LPS) is a potent virulence factor of pathogenic Gram-negative bacteria. To better understand the role of LPS in host-pathogen interactions and to elucidate the antigenic and immunogenic properties of LPS inner core region, a collection of well-defined l-glycero-d-manno-heptose (Hep) and 3-deoxy-α-d-manno-oct-2-ulosonic acid (Kdo)-containing inner core oligosaccharides is required. To address this need, we developed a diversity-oriented approach based on a common orthogonal protected disaccharide Hep-Kdo. Utilizing this new approach, we synthesized a range of LPS inner core oligosaccharides from a variety of pathogenic bacteria including Y. pestis, H. influenzae, and Proteus that cause plague, meningitis, and severe wound infections, respectively. Rapid access to these highly branched core oligosaccharides relied on elaboration of the disaccharide Hep-Kdo core as basis for the elongation with various flexible modules including unique Hep and 4-amino-4-deoxy-β-l-arabinose (Ara4N) monosaccharides and branched Hep-Hep disaccharides. A regio- and stereoselective glycosylation of Kdo 7,8-diol was key to selective installation of the Ara4N moiety at the 8-hydroxyl group of Kdo moiety of the Hep-Kdo disaccharide. The structure of the LPS inner core oligosaccharides was confirmed by comparison of 1H NMR spectra of synthetic antigens and isolated fragments. These synthetic LPS core oligosaccharides can be covalently bound to carrier proteins via the reducing end pentyl amine linker, to explore their antigenic and immunogenic properties as well as potential applications such as diagnostic tools and vaccines.