Deoxy-D-manno-octulosonic acid

These results have been used to prepare key starting compounds 11 and 12 for the enantioselective synthesis of 3-deoxy-D-manno-2-octulosonic acid... 

Upon treatment with n-BruiNF, product 97 is converted to 98, which is a key intermediate for the synthesis of the monosaccharide 3-deoxy-D-manno-2-octulosonic acid (KDO)—an essential constituent of the outer membrane lip-op oly s accharide (LPS) of gram-negative bacteria.40... 

THE CHEMISTRY AND BIOLOGICAL SIGNIFICANCE OF 3-DEOXY-D-manno-2-OCTULOSONIC ACID (KDO) ... 

R. Ramage, A. M. MacLeod, and G. W. Rose, Dioxolanes as synthetic intermediates. Part 6. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-deoxy-D-araMiio-2-heptulosonic acid (DAH) and 2-keto-3-deoxy-D-gluconic acid (KDG), Tetrahedron 47 5625 (1991). 

A. Dondoni and P. Merino, Chemistry of the enolates of 2-acetylthiazole Aldol reactions with chiral aldehydes to give 3-deoxy aldos-2-uloses and 3-deoxy-2-ulosonic acids. A short total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), J. Org. Chem. 56 5294 (1991). 

Among nucleoside glycosyl monophosphates, the primary derivatives include cytidine (N-acetyl neuraminic monophosphate) (CMP-NeuAc),51 in which the n-glycero-fi-n-galacto configuration of the monosaccharide group has been confirmed,52 and the analogous derivative of 3-deoxy-D-manno-2-octulosonic acid.53,54... 

Two of the most frequent monosaccharide components of bacterial polymers belonging to this group have been the subjects of articles in this Series. They are 3-deoxy-D-manno-2-octulosonic acid,247 a normal constituent of the core region of bacterial lipopolysaccharides that is also present in some other polymers, and N-acetylneuraminic acid,248 found in several capsular polysaccharides. Enolpyruvate phosphate serves as the precursor of the C-l-C-3 fragment of the monosaccharides, with D-arabinose 5-phosphate or 2-acetamido-2-deoxy-D-mannose 6-phosphate being an acceptor for transfer of the three-carbon unit. Characteristic, activated forms of these monosaccharides are the CMP derivatives. 

Unger, F. M. The Chemistry and Biological Significance of 3-Deoxy-D-manno-2-octulosonic Acid (KDO), Tipson, R. S7 Horton, D., eds. ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, Vol. 

Neszmelyi, A., Jann, K., Messner, P. and Unger, F.M. (1982) Constitutional and configurational assignements by JC NMR spectroscopy of Escherichia coli capsular polysaccharides containing ribose and 3-deoxy-D-manno-2-octulosonic acid (KDO). J. Chem. Soc. Chem. Commun. 1017-1019... 

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