Sialyl-Lewis analogues

W. Stahl, U. Sprengard, G. Kretzschmar, and H. Kunz, Synthesis of deoxy sialyl Lewis analogues, potential selectin antagonists, Angew. Chem. Int. Ed. Engl. 33 2096 (1994). 

In the first quarter of 1999, C3ftel Corporation, La Jolla, CA announced the results from the Cylexin (CY1503, sialyl Lewis analogue) Phase E/in clinical trials (treatment of reperfusion injury in infants undergoing corrective surgery for congenital heart disease), which indicated that Cylexin showed no beneht over the placebo. 

Thoma, G, Magnani, J L, Patton, J T, Ernst, B, Jahnke, W, Preorganization of the bioactive conformation of sialyl Lewis analogues correlates with their affinity to E-selectin, Angew. Chem. Int. Ed., 40, 1941-1945, 2001. 

Dekany, G, Wright, K, Ward, P, Toth, I, Synthesis of sialyl Lewis analogues, J. Carbohydr. Chem., 15, 383-398, 1996. 

Using the same procedure, the synthesis of the thiogalabioside (87b) was reported very recently [54]. Also, this year an orthogonal synthesis of a thio-linked analogue of the sialyl Lewis X (93) has been described using known coupling reactions (Scheme 26) [55]. 

The same group recently reported the chemical synthesis of sialyl-Lewis X and A epitope analogues containing the N-methyl derivative of (33) [87]. 

With the continuous development of new methods and improvement of old methods, the construction of more and more complex thiooligosaccharides has become possible. Two recently published examples of this are shown in O Scheme 66 and O Scheme 67. In O Scheme 66 the synthesis of thio analogues of Lewis x and sialyl-Lewis x, using exclusively non-anomeric thiols in both acid-and base-catalyzed glycosylation reactions, is summarized [195]. 

Analogues of the Sialyl Lewis Group and of the N-Acetylneuraminic Acid in the Antiadhesion Therapy... 

The Sialyl Lewis Group and its Analogues as Ligands for Selectins Chemoenzymatic Synthesis and Biological Functions... 

Nine new zwitterionic digalactosyl ceramides isolated from the earthworm Pheretima asiatica all had a choline phosphate ester group at the 6-position of the terminal galactosyl moiety. A sialyl Lewis X analogue in which the sialic acid residue is replaced by a galactosyl residue bearing a phosphate group is referred to in Part 3 below (Ref. 78). 

En route to a Sialyl Lewis X analogue containing l,4,5,6-tetradeoxy-l,4-... 

In the synthesis of a Sialyl Lewis X analogue, l,4,5,6-tetradeoxy-l,4-imino-D-ido-hexitol (for synthesis see Section 1.3.1) was a-L-fucosylated at the less hin> dered (C-2) hydroxyl, then p-D-galactosylated at 0-3 to produce a non-sulfated precursor to the pseudo-trisaccharide 137. ... 

---