Mimics of the sialyl Lewis X tetrasaccharide. Replacement of the N-acetylglucosamine sugar with simple C2-symmetric 1,2-diols.
Analogues of sialyl Lewis X have been synthesized that feature replacement of the N-acetylglucosamine residue with C2-symmetric diols. The diols used contain different levels of torsional constraint and various functional groups. The cyclohexyl derived compound 27 was equipotent to sLex in vitro (IC50 0.5 mM).
Prodger
J C
JC
Department of Medicinal Chemistry, Glaxo Research and Development Ltd, Glaxo Wellcome Medicines Research Centre, Stevenage, Herts, UK.
Bamford
M J
MJ
Bird
M I
MI
Gore
P M
PM
Holmes
D S
DS
Priest
R
R
Saez
V
V
D000117:Acetylglucosamine / Q000737:chemistry*; D002240:Carbohydrate Sequence; D019040:E-Selectin / Q000737:chemistry; D018922:HL-60 Cells; D006801:Humans; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000037:antagonists & inhibitors / Q000737:chemistry*; D000080506:Sialyl Lewis X Antigen; D013057:Spectrum Analysis
D019040:E-Selectin; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D000117:Acetylglucosamine