Efficient synthesis of polylactosamine structures through regioselective glycosylations

Journal of Carbohydrate Chemistry

Volumn 20, Issue 7-8, 2001, Pages 569-583

  Buskas, Therese ^a   Konradsson, Peter ^b   Oscarson, Stefan ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b LINKÖPING UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035648753     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100108275     Document Type: Article

References (24)

1. th birthday.
2. Renkonen, O. Enzymatic glycosylations with glycosyltransferases. In Carbohydrates in Chemistry and Biology. Part 1: Chemistry of Saccharides; Ernst, B; Hart, G. W.; Sinaÿ, P. (Eds); Wiley-WCH, Weinheim, 2000; Vol. 2, pp 647-661.
3. Alais, J.; Veyrières, A. Block synthesis of a hexasaccharide hapten of I-blood group antigen. Tetrahedron Lett. 1983, 24, 5223-5226.
4. Alais, J.; Veyrières, A. Synthesis of an octasaccharide fragment of the polylactosamine series by a blockwise approach. Tetrahedron Lett. 1987, 28, 3345-3348.
5. Alais, J.; Veyrières, A. Synthesis of linear tetrasaccharide, hexasaccharide, and octasaccharide fragments of the I-blood group active poly-(n-acetyl-lactosamine) series-blockwise methods for the synthesis of repetitive oligosaccharide sequences. Carbohydr. Res. 1990, 207, 11-31.
6. Srivastava, G.; Hindsgaul, O. Synthesis of polylactosamine oligomers by disaccharide polymerization. J. Carbohydr. Chem. 1991, 10, 927-933.
7. Shimizu, H.; Ito, Y.; Kanie, O.; Ogawa, T. Solid phase synthesis of a polylactosamine oligosaccharide. Bioorg. Med. Chem. Lett. 1996, 6, 2841-2846.
8. Nilsson, M.; Norberg, T. Synthesis of carbohydrate derivatives corresponding to a tumor-associated glycolipid: a trimeric Lewis x nonasaccharide and a trimeric N-acetyl lactosamine hexasaccharide. J. Carbohydr. Chem. 1989, 8, 613-627.
9. Salminen, H.; Ahokas, K.; Niemela, R.; Penttila, L.; Maaheimo, H.; Helin, J.; Costello, C. E.; Renkonen, O. Improved enzymic synthesis of a highly potent oligosaccharide antagonist of L-selectin. FEBS Lett. 1997, 419, 220-226.
10. Barrondes, S. H.; Cooper, D. N. W.; Gitt, M. A.; Leffler, H. Galectins-Structure and function of a large family of animal lectins. J. Biol. Chem. 1994, 269, 20807-20810.
11. Perillo, N. L.; Marcus, M. E.; Baum, L.G. Galectins: Versatile modulators of cell adhesion, cell proliferation, and cell death. J. Mol. Med. 1998, 76, 402-412.
12. Arnarp, J.;Lönngren, J. Synthesis of a tri-saccharide, a penta-saccharide, and a hepta-saccharide containing terminal N-acetyl-β-D-lactosaminyl residues, part of the complex-type carbohydrate moiety of glycoproteins. J. Chem. Soc. Perkin Trans 1 1981, 2070-2074.
13. Kaji. E.; Lichtenthaler, F. W. Expedient conversion of lactose into versatile derivatives of lactosamine and β-D-galactosyl-(1-→4)-D-mannosamine. J. Carbohydr. Chem. 1995, 4, 791-803.
14. Wrodnigg, T. M.; Stütz, A. E. The Heyns rearrangement revisited: An exceptionally simple two-step chemical synthesis of D-lactosamine from lactulose. Angew. Chem. Int. Ed. 1999, 38, 827-828
15. 3Na Lewis X and Lewis A structures. Carbohydr. Res. 1996, 280, 261-276.
16. Numomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Total synthesis of sulfated Le(X) pentasoyl ceramide. Carbohydr. Res. 1994, 263, C1-C6.
17. Zhang, Y.-M.; Brodsky, A.; Sinaÿ, P.; Saint-Marcoux, G.; Perly, B. Synthesis of a nonasaccharide with two Lewis X trisaccharides anchored onto a branched trimannoside. Tetrahedron: Asymmetry 1995, 6, 1195-1216.
18. Ellervik, U.; Magnusson, G. A high yielding chemical synthesis of a sialyl Lewis X tetrasaccharide and Lewis X trisaccharide; Example of regio-and stereodifferentiated glycosylations. J. Org. Chem. 1998, 63, 9314-9322.
19. Debenham, J. S.; Debenham, S. D.; Fraser-Reid, B. N-Tetrachlorophthaloyl (TCP) for ready protection/deprotection of amino sugar glycosides. Bioorg. Med. Chem. 1996, 4, 1909-1918.
20. Buskas, T.; Konradsson, P. Synthesis of oligosaccharides designed to form micelles, corresponding to structures found in ovarian cyst fluid. J. Carbohydr. Chem. 2000, 79, 25-51.
21. 4Cer. Carbohydr. Res. 1986, 155, C1-C5.
22. Okamoto, K.; Goto, T. Glycosidation of sialic acid. Tetrahedron 1990, 46, 5835-5837.
23. Byramova, N. E.; Ovchinnikov, M. V.; Backinovsky, L. V.; Kochetkov, N. K. Selective removal of O-acetyl groups in the presence of O-benzoyl groups by acid-catalyzed methanolysis. Carbohydr. Res. 1983, 124, C8-C11.
24. Olsson, L.; Kelberlay, S.; Jia, Z. J.; Fraser-Reid, B. Access to tetrachlorophthalimide-protected ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranosides. Carbohydr. Res. 1998, 314, 273-276.