Development of Efficient Methodologies for Kdo Glycosides

Kdo, or 3-deoxy-D-manno-oct-2-ulosonic acid, is an 8-carbon monosaccharide expressed by gram-negative bacteria which produce characteristic lipopolysaccharides (LPS). - The negatively charged polysaccharides play a vital role in protecting the structural integrity of the bacterial cell membranes. Kdo glycosides exist as the α-anomer in the majority of the LPS structures; however, β-anomeric form has also found in some gram-negative bacteria as well as in the capsular polysaccharides of some gram-positive bacteria. We have developed a family of 1-C-glycals for the efficient synthesis of both α- and β-Kdo glycosides.

References

Y. Qian, J. Feng and C.-C. Ling, J. Org. Chem., 77, 96-107 (2012).