Collect. Czech. Chem. Commun. 2004, 69, 1781-1804

Synthesis of Linear and Branched Regioisomeric Chitooligosaccharides as Potential Mimetics of Natural Oligosaccharide Ligands of Natural Killer Cells NKR-P1 and CD69 Lectin Receptors

Anna Rohlenováa, Miroslav Ledvinaa,*, David Šamana and Karel Bezouškab

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-166 10, Prague 6, Czech Republic
b Department of Biochemistry, Faculty of Science, Charles University, Hlavova 8, CZ-128 40 Prague 2, Czech Republic


Regioisomer of chitobiose 13 with β(1→3) glycosidic bond and branched analog of chitotriose 25 having β(1→4) and β(1→3) glycosidic bonds, were prepared and tested as potential mimetics of natural oligosaccharide ligands for activating lectin receptors NKR-P1A and CD69 of natural killer (NK) cells. The structural requirements of NKR-P1 lectin receptor on effective mimetics of its natural ligands has been discussed. A significant binding activity of the branched trisaccharide 25 to the receptor CD69 was observed.

Keywords: Carbohydrates; Oligosaccharides; Aminosugars; D-Glucosamine; Glycosylation; Glycosides; NK cells; NKR-P1 and CD69 lectin receptors; Lectins; Immunotherapeutics.

References: 26 live references.