Sialyl Lewis enzymatic synthesis

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. 

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. 

A chemoenzymatic synthesis of di-, tetra-, and octavalent sialyl Lewis X ligands scaffolded on dendrimers has been reported (Scheme 67). 508 Hypervalent L-lysine cores with covalently attached 2-acetamido-2-deoxy-D-glucose residues were chemically prepared and enzymatically transformed into sialyl Lewis X-containing dendrimers using (3-(l— 4) ga-... 

Enzymatic glycosylation on SP was first reported by Schuster et al. (157) and since then has been used to perform multiple glycosylations. Two examples are reported in Fig. 2.28. The synthesis of oligosaccharides 2.94 and 2.95 related to the sialyl Lewis X antigen was carried out via glycosylations mediated by P-l,4-galactosyltransferase and a-2,3-sialyltransferase (171) and by p-l,4-galactosyltransferase, a-2,3-sialyl-transferase, and fucosyltransferase (172), respectively. The use of unprotected saccha-... 

Gutierrez Gallego R, Dudziak G, Kragl U, Wandrey C, Kamer-ling JP, VUegenthart IF. Enzymatic synthesis of the core-2 sialyl Lewis X O-glycan on the tumor-associated MUCla peptide. Biochimie 2003 85 275-286. 

Blixt O, Norberg T. Solid-phase enzymatic synthesis of a sialyl lewis X tetrasaccharide on a sepharose matrix. J. Org. Chem. 1998 63 2705-2710. 

Ichikawa Y, Lin Y-C, Dumas DP, Shen G-J, Garcia-Junceda E, Williams MA, Bayer R, Ketcham C, Walker LE, Paulson JC, Wong C-H. Chemical-enzymatic synthesis and conformational analysis of Sialyl Lewis X and derivatives. J. Am. Chem. Soc. 1992 114 9283-9298. 

Sallas, F, Nishimura, S-I, Chemo-enzymatic synthesis of glycopolymers and sequential glycopeptides hearing lactosamine and sialyl Lewis unit pendant chains, J. Chem. Soc. Perkin Trans. 1, 2091-2103, 2000. 

Interaction between the glycoprotein E-selectin (expressed on the surface of endothelial cells) and the sialyl Lewis 1 ligand structures on the surface of neutrophils is a major event in inflammation, infection, and metastasis. Both chemical and enzymatic syntheses have been described for the synthesis of the sialyl Lewisx structure. A summary of the general strategy used in chemoenzymatic synthesis is shown here. Extensive in situ regenerations of the sugar nucleotides are not shown in the scheme.97... 

---