Published TCIMAIL newest issue No.197
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Affordable, Crystalline and Bench-stable Derivative of L-glycero-D-manno Heptose
The higher-carbon sugar L-glycero-D-manno heptose (LD-heptose) is a central and conserved constituent of the lipopolysaccharide (LPS), which is located in the cell walls of Gram-negative bacteria and exhibits major interactions with the host’s immune system. Consequently, ever since its discovery in the 1980s, LD-heptose-containing structures have been in the focus of research activities aiming at next generation antibiotic agents or at vaccine strategies.
H1657 can serve as a common starting point to short routes to parent LD-heptose, chromogenic probes (e.g. for screenings for heptose processing enzymes), as well as to suitable donor and acceptor building blocks required for the assembly of bacterial oligosaccharides. And it will invite new research groups to enter this challenging but important field of bacterial cell wall glycosides promising great potential for future directions in the ongoing combat against microbial infections.
Advantages
- Hexaacetyl Ester of Heptose Commonly Located in Cell Walls of Gram-negative Bacteria
- Applicable to the Synthesis of LPSs (LipoPolySaccharides)
References
- 1) Synthesis of a trisaccharide of the inner core region of Citrobacter PCM 187 lipopolysaccharide that contains l-glycero-α-d-manno-heptopyranosyl units
- 2) Synthesis of Pseudomonasaeruginosa lipopolysaccharide core antigens containing 7-O-carbamoyl-l-glycero-α-d-manno-heptopyranosyl residues
- 3) Characterization of the α-1,2-N-acetylglucosaminyltransferase of Neisseria gonorrhoeae, a key control point in lipooligosaccharride biosynthesis
- 4) Synthesis of a spacer-linked derivative of heptopyranosyl(α1-3)heptopyranose expressed in lipooligosaccharide and lipopolysaccharide.
