Sialylation

In the second example, the synthesis of an I-active ganglioside analogue98 is covered. The sialyl I antigen is shown in Scheme 14. 

Flgure10.23 Sialyl Lewis -related selectin inhibitorandfluorogenicscreening compound for transketolase prepared using enzymatic aldolization, and multienzymatic oxidation-aldolization strategy for the synthesis of bicyclic higher carbon sugars. 

Fluorogenic compound (56) for transketolase assays has been prepared making use of FruA specificity [123]. Pendant anionically charged chains have been extended from O- or C-glycosidic aldehydes to furnish low molecular weight mimics of the sialyl Lewis X tetrasaccharide such as (SS) (Figure 10.23) [124], Other higher carbon... 

Selectins L-selectin PMN, lymphs CD34,Gly-CAM-L Sialyl-Lewis" and others... 

The precise chemical nature of some of the ligands involved in selectin-ligand interactions has been determined. All three selectins bind sialylated and fucosy-lated oligosaccharides, and in particular all three bind sialyl-Lewis (Figure 47-12), a structure present on both glycoproteins and glycolipids. Whether this compound is the actual ligand involved in vivo is not estab-... 

Figure 47-12. Schematic representation of the structure of sialyl-lewis . ...

Berry, C.N., Lloyd, K.G. and Louisot, P. (1992). Effects of S-carboxymethyl-L-cysteine on pulmonary sialyl transferease activity in vitro, in healthy and in sulphur dioxide induced bronchitic rats. Fund. Clin. Pharmacol. 6, 29-35. 

SLE Systemic lupus erythematosus SLe Sialyl Lewis X antigen SLO Streptolysin-O SLPI Secretory leucocyte protease inhibitor... 

Shen, Z., Warren, C.D., and Newburg, D.S., High-performance capillary electrophoresis of sialylated oligosaccharides of human milk, Anal. Biochem., 279, 37, 2000. 

Bannert N, Craig S, Farzan M, et al. Sialylated O-glycans and sulfated tyrosines in the NH2-terminal domain of CC chemokine receptor 5 contribute to high affinity binding of chemokines. J Exp Med 2001 194(11) 1661-1673. 

Yang W, Fan H, Gao X et al (2004) The first fluorescent diboronic acid sensor specific for hepatocellular carcinoma cells expressing sialyl Lewis X. Chem Biol 11 439 148... 

The recent impressive work from Hamilton and Gerngross [66] about controlled humanization of iV-glycosylation opened up very attractive perspectives for yeasts for large-scale production of eukaryotic fully humanized sialylated glycoproteins. That makes them serious... 

Savage, A.V., Donohue, J.J., Koeleman, C.A.M. and van den Eijnden, D.H. (1990) Structural characterization of sialylated tetrasaccharides and pentasaccharides with blood-group H and Lex activity isolated from bovine submaxillary mucin. European Journal of Biochemistry 193, 837-843. 

Washiya, K., Furuike, T., Nakajima, F., Lee, Y. C. and Nishimura, S. I. (2000). Design of fluorogenic substrates for continuous assay of sialyl-transferase by resonance energy transfer. Anal. Biochem. 283, 39-48. 

Fig. 19. Cyclodextrins decorated with sugars, including sialic acid and sialyl oligosaccharides. 

T. Furiuke, R. Sadamoto, K. Niikura, K. Monde, N. Sakairi, and S.-I. Nishimura, Chemical and enzymatic synthesis of glycocluster having seven sialyl lewis X arrays using /i-cyclodextrin as a key scaffold material, Tetrahedron, 61 (2005) 1737-1742. 

H. Oka, T. Onaga, T. Koyama, C.-T. Guo, Y. Suzuki, Y. Esumi, K. Hatano, D. Temnuma, and K. Matsuoka, Sialyl 7(2 3) lactose clusters using carbosilane dendrimer core scaffolds as influenza hemagglutinin blockers, Bioorg. Med. Chem. Lett., 18 (2008) 4405 1408. 

---