Synthesis of 3″- and 4″-deoxy-Lewisx trisaccharides: A useful tool for study of carbohydrate-carbohydrate interaction
Synthesis of 3″-deoxy and 4″-deoxy Lewisx trisaccharides is described. Phenyl 2,3,6-tri-O-benzoyl-4-deoxy-1-thio-β-d-xylo-hexopyranoside was condensed with a diol of glucosamine to give regio- and stereo-selectively a disaccharide. Stereoselective fucosylation of this disaccharide provided a protected deoxy Lewisx trisaccharide which was deprotected to give the 4″-deoxy Lewisx trisaccharide. Application of the similar synthetic sequence provided the 3″-deoxy Lewisx trisaccharide.
Keywordscarbohydrate glycosylation synthesis trisaccharide
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- 4.Eggens I, Fenderson B, Toyokuni T, Dean B, Stroud M, Hakomori S. Specific interaction between Lex and Lex determinants. J Biol Chem, 1989, 264: 9476–9484Google Scholar
- 5.Kojima N, Fenderson BA, Stroud MR, Goldberg RI, Habermann R, Toyokuni T, Hakomori S. Further studies on cell adhesion based on Lex-Lex interaction, with new approaches: Embryoglycan aggregation of F9 teratocarcinoma cells, and adhesion of various tumour cells based on Lex expression. Glycoconjugate J, 1994, 11: 238–248CrossRefGoogle Scholar
- 9.Geyer A, Gege C, Schmidt RR. Calcium-dependent carbohydrate-carbohydrate recognition between Lewisx blood group antigens. Angew Chem Int Ed, 2000, 39: 3246–3249Google Scholar
- 10.Gege C, Geyer A, Schmidt RR. Carbohydrate-carbohydrate recognition between Lewis X blood group antigens, mediated by calcium ions. Eur J Org Chem, 2002, 2475–2485Google Scholar
- 24.Lönn H. Synthesis of a tri- and a hepta-saccharide which contain α-L-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins. Carbohydr Res, 1985, 139: 105–113Google Scholar