Deaminated neuraminic acid

M. Kimura, Y. Hama, T. Sumi, M. Asakawa, R. B. N. Narasinga, A. P. Home, S.-C. Li, Y.-T. Li, and H. Nakagawa, Characterization of a deaminated neuraminic acid-containing glycoprotein from the skin mucus of the loach, Misgurnus anguillicaudatus, J. Biol. Chem., 269 (1994) 32138-32143. 

The sialic acid aldolase-catalyzed condensation of D-mannose 8 and pyruvate led, in an excellent yield, to the synthesis of KDN 9 [33], a natural deaminated neuraminic acid first isolated from rainbow trout eggs [34] and then discovered in other species. The discovery that sialic acid aldolase accepts as substrates D-mannose substituted on the 2-position, even by bulky substituents such as phenyl, azido, or bromine, opened the route to novel unnatural sialic acid derivatives [35-39]. Pentoses also are substrates. N-Substituted neuraminic acids could be prepared either directly from the corresponding Af-substituted mannosamine, such as N-thioacyl derivatives [40], or after reduction and acylation of 5-azido-KDN [41]. Recently, AT-carbobenzyloxy-D-mannosamine was converted, in a good yield, into the N-carbobenzyloxy-neurarninic acid, further used as a precursor of a derivative of castanospermine [42]. 

C. Aug6 and C. Gautheron, The use of an immobilized aldolase in the first synthesis of a natural deaminated neuraminic acid, J. Chem. Soc., Chem. Commun. p. 860 (1987). 

D. Nadano, M. Iwasaki, S. Endo, K. Kitajima, S. Inoue, and Y. Inoue, A naturally occurring deaminated neuraminic acid, 3-deoxy-D-gfycero-D-galacIo-nonulosonic acid (KDN), J. Biol. Chem. 267 11550 (1986). 

A. M. Gil-Serrano, M. A. Rodriguez-Carvajal, P. Tejero-Mateo, J. L. Espartero, J. Thomas-Oates, J. E. Ruiz-Sainz, and A. M. Buendia-Claveria, Structural determination of a 5-O-methyl-deaminated neuraminic acid (Kdn)-containing polysaccharide isolated from Sinorhizobiumfredii, Biochem. J., 334 (1998) 585-594 B. Lindberg, Components of bacterial polysaccharides, Adv. Carbohydr. Chem. Biochem., 48 (1990) 279-318 L. L. MacLean and M. B. Perry, Structural characterization of the serotype 0 5 O-polysaccharide antigen of the lipopolysaccharide of Escherichia coli 0 5, Biochem. Cell Biol., 75 (1997) 199-205. 

The term sialic acid (Sia) refers to a group of nine-carbon a-keto acids derived from Neu5Ac, 5-glycolylneur-aminic acid (Neu5Gc), and deaminated neuraminic acid (KDN) (Figure 20). A closely related keto-deoxy acid,... 

Polysialic acid can be composed of 5-V-acetylneuraminic acid (Neu5Ac), 5-V-glycolylneuraminic acid (Neu5Gc), or deaminated neuraminic acid (KDN) residues, which are usually joined by a2,8, a2,9, or alternating a2,8/a2,9 ketosidic linkages [47-53]. 

Inoue S, Kitajima K (2006) KDN (deaminated neuraminic acid) dreamful past and exciting future of the newest membw of the sialic acid family. Glycoconj J 23 277-290... 

Kanamori A, Inoue S, Xulei Z, Zuber C, Roth J, Kitajima K, Ye J, Troy FA 2nd, Inoue Y (1994) Monoclonal antibody specific for a2,8-linked oligo deaminated neuraminic acid (KDN) sequences in glycoproteins. Preparation and characterization of a monoclonal antibody and its application in immunohistochemistry. Histochemistry 101 333-340... 

Angata T, Matsuda T, Kitajima K (1998) Synthesis of neoglycoconjugates containing deaminated neuraminic acid (KDN) using rat liver a2,6-sialyltransferase. Glycobiology 8 277-284... 

Inoue, Y., 1993, Glycobiology of fish egg polysialoglycoproteins (PSGP) and deaminated neuraminic acid-rich glycoproteins (KDN-gp), in Polysialic Acid (J. Roth, U. Rutishauser, and F. A. Troy II, eds.), Birkhauser, Basel, pp. 171-181. 

Kanamori, A., Inoue, S., Iwasaki, M., Kitajima, K., Kawai, G., Yokoyama, S., and Inoue, Y, 1990, Deaminated neuraminic acid rich glycoprotein of rainbow trout egg vitelline envelope Occurrence of a novel a-2,8-linked oligo (deaminated neuraminic acid) structure in O-linked glycan chains, J. Biol. Chem. 265 21811-21819. 

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