Synthesis of human milk oligosaccharides: 2'- and 3'-fucosyllactose

Heterocycles

Volumn 84, Issue 1, 2011, Pages 637-655

  Pereira, Claney L ^a   McDonald, Frank E ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84855968851     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)37     Document Type: Article

References (46)

1. R. E. Black, S. S. Morris, and J. Bryce, Lancet, 2003, 361, 2226.
2. J. Brand Miller and P. McVeagh, Br. J. Nutr., 1999, 82, 333
3. C. Kunz, S. Rudloff, W. Baier, N. Klein, and S. Strobel, Annu. Rev. Nutr., 2000, 20, 699
4. D. S. Newburg, G. M. Ruiz-Palacios, and A. L. Morrow, Annu. Rev. Nutr., 2005, 25, 37
5. L. Bode, J. Nutrition, 2006, 136, 2127
6. M. R. Ninonuevo, Y. Park, H. Yin, J. Zhang, R. E. Ward, B. H. Clowers, J. B. German, S. L. Freeman, K. Killeen, R. Grimm, and C. B. Lebrilla, J. Agric. Food Chem., 2006, 54, 7471
7. S. M. Donovan, Br. J. Nutr., 2009, 101, 1267.
8. G. V. Coppa, L. Zampini, T. Galeazzi, B. Facinelli, L. Ferrante, R. Capretti, and G. Orazio, Pediatr Res., 2006, 59, 377
9. R. Maria Espinosa, M. Tamiz, and P. Prieto, Br. J. Nutr., 2007, 98, S74.
10. L. Bode, Nutr. Rev., 2009, 67, S183
11. Y. Vandenplas, Br. J. Nutr., 2002, 87, S293.
12. B. Wang and J. Brand-Miller, Eur. J. Clin. Nutr., 2003, 57, 1351
13. B. Wang, J. Brand-Miller, P. McVeagh, and P. Petocz, Am. J. Clin. Nutr., 2001, 74, 510.
14. G. M. Ruiz-Palacios, L. E. Cervantes, P. Ramos, B. Chavez-Munguia, and D. S. Newburg, J. Biol. Chem., 2003, 278, 14112
15. A. L. Morrow, G. M. Ruiz-Palacios, X. Jiang, and D. S. Newburg, J. Nutrition, 2005, 135, 1304.
16. S. A. Abbas, J. J. Barlow, and K. L. Matta, Carbohydr. Res., 1981, 88, 51
17. A. Fernandez-Mayoralas, and M. Martin-Lomas, Carbohydr. Res., 1986, 154, 93
18. R. K. Jain, R. D. Locke, and K. L. Matta, Carbohydr. Res., 1991, 212, C1
19. M. Izumi, O. Tsuruta, S. Harayama, and H. Hashimoto, J. Org. Chem., 1997, 62, 992
20. A. Rencurosi, L. Poletti, G. Russo, and L. Lay, Eur. J. Org. Chem., 2003, 1672.
21. For a synthesis using metabolically engineered E. coli, see: S. Drouillard, H. Driguez, and E. Samain, Angew. Chem. Int. Ed., 2006, 45, 1778.
22. R. R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 1994, 50, 21
23. G. Kretzschmar and W. Stahl, Tetrahedron, 1998, 54, 6341
24. F. Jamois, F. Le Goffic, J. C. Yvin, D. Plusquellec, and V. Ferrières, Open Glycoscience, 2008, 1, 19.
25. Y. Matsuzaki, Y. Ito, and T. Ogawa, Tetrahedron Lett., 1992, 33, 4025.
26. K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 1987, 43, 5919.
27. G. Zheng, A. Graham, M. Shibata, J. R. Missert, A. R. Oseroff, T. J. Dougherty, and R. K. Pandey, J. Org. Chem., 2001, 66, 8709.
28. T. Tomoo, T. Kondo, H. Abe, S. Tsukamoto, M. Isobe, and T. Goto, Carbohydr. Res., 1996, 284, 207.
29. P. J. Garegg and T. Norberg, Carbohydr. Res., 1976, 52, 235.
30. H.-J. Vermeer, C.-M. van Dijk, J.-P. Kamerling, and J.-F. G. Vliegenthart, Eur. J. Org. Chem., 2001, 193.
31. S. Inamura, Y. Fujimoto, A. Kawasaki, Z. Shiokawa, E. Woelk, H. Heine, B. Lindner, N. Inohara, S. Kusumoto, and K. Fukase, Org. Biomol. Chem., 2006, 4, 232
32. D. Hamza, R. Lucas, T. Feizi, W. Chai, D. Bonnaffé, and A. Lubineau, ChemBioChem., 2006, 7, 1856
33. S. Ronchi, F. Compostella, L. Lay, F. Ronchetti, and L. Toma, Eur. J. Org. Chem., 2005, 4459.
34. R. Windmüller and R. R. Schmidt, Tetrahedron Lett., 1994, 35, 7927
35. L. Lay, R. Windmüller, S. Reinhardt, and R. R. Schmidt, Carbohydr. Res., 1997, 303, 39
36. C. Gege, S. Oscarson, and R. R. Schmidt, Tetrahedron Lett., 2001, 42, 377
37. C. Gege, A. Geyer, and R. R. Schmidt, Eur. J. Org. Chem., 2002, 2475
38. B. La Ferla, D. Prosperi, L. Lay, G. Russo, and L. Panza, Carbohydr. Res., 2002, 337, 1333
39. A. Rencurosi, L. Poletti, G. Russo, and L. Lay, Eur. J. Org. Chem., 2003, 1672.
40. R. R. Schmidt and A. Toepfer, Tetrahedron Lett., 1991, 32, 3353.
41. Only 38% yield of the trisaccharide 19 was obtained when the TMSOTf catalyst was added to a cold (-5°C) CH2Cl2 solution of lactosyl acceptor 9 and fucosyl donor 18.
42. Under otherwise identical conditions, the corresponding 2,3,4-triacetate fucosyl trichloroacetimidate provided only the undesired beta-anomer of 19.
43. The formation of trisaccharide 19 was accompanied by variable amounts of a byproduct which was possibly the tetrasaccharide, from a second fucosylation at O3 of 19. However, this byproduct could not be fully purified nor characterized, although its production increased with corresponding decreases in the yield of 19 when 2 equiv of fucosyl donor 18 was used in the glycosylation. We did not observe any trisaccharide corresponding to O3-glycosylation alone.
44. The formation of trisaccharide 19 was accompanied by variable amounts of a byproduct which was possibly the tetrasaccharide, from a second fucosylation at O3 of 19. However, this byproduct could not be fully purified nor characterized, although its production increased with corresponding decreases in the yield of 19 when 2 equiv of fucosyl donor 18 was used in the glycosylation. We did not observe any trisaccharide corresponding to O3-glycosylation alone. 22. T. Rundlöf and G. Widmalm, Magn. Reson. Chem., 2001, 39, 381
45. G. A. Jenkins, J. H. Bradbury, M. Messer, and E. Trifonoff, Carbohydr. Res., 1984, 126, 157
46. Y. Ishizuka, T. Nemoto, M. Fujiwara, K. Fujita, and H. Nakanishi, J. Carbohydr. Chem., 1999, 18, 522.