Efficient synthesis of two sialylated tetrasaccharides found in goat milk

Synthesis

Volumn , Issue 8, 2009, Pages 1348-1354

  Mandal, Pintu Kumar ^a   Misra, Anup Kumar ^a  

^a BOSE INSTITUTE   (India)

Author keywords

Glycosylations; Goat milk; Oligosaccharides; Sialic acid; Tetrasaccharides

Indexed keywords

CONCISE SYNTHESIS; EFFICIENT SYNTHESIS; GLYCOSYLATIONS; GOAT MILK; GROUP MANIPULATIONS; KEY FEATURE; REGIO-SELECTIVE; SIALIC ACID; SYNTHETIC STRATEGIES; TETRASACCHARIDES;

ACIDS; CARBOXYLIC ACIDS; OLIGOSACCHARIDES; POLYSACCHARIDES;

SYNTHESIS (CHEMICAL);

4 METHOXYPHENYL GROUP; DISACCHARIDE; PROTECTIVE AGENT; TETRASACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSYLATION; GOAT; ISOMERISM; MILK; NONHUMAN; SYNTHESIS;

EID: 67650021194     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088032     Document Type: Article

References (49)

1. (a) Newburg, D. S.; Neubaur, S. H. Handbook of Milk Composition; Academic Press: San Diego, 1995, 273-349.
2. (b) Stahl, B.; Thurl, S.; Zeng, J.; Karas, M.; Hillenkamp, F.; Steup, M.; Sawatzki, G. Anal. Biochem. 1994, 223, 218.
3. (a) Holmgren, J.; Svennerholm, A. M.; Lindblad, M. Infect. Immun. 1983, 39, 147.
4. (b) Chaturvedi, P.; Warren, C. D.; Altaye, M.; Morrow, A. L.; Ruiz-Palacios, G.; Pickering, L. K.; Newburg, D. S. Glycobiology 2001, 11, 365.
5. (c) Gothefors, L.; Olling, S.; Winberg, J. Acta Pediatr. Scand. 1975, 64, 807.
6. (d) Andersson, B.; Porras, O.; Hanson, L. A.; Lagergard, T.; Svanborg-Eden, C. J. Infect. Dis. 1986, 153, 232.
7. (e) Coppa, G. V.; Gabrielli, O.; Pierani, P.; Catassi, C.; Carlucci, A.; Giorgi, P. Pediatrics 1993, 91, 637.
8. (f) Crane, J. K.; Azar, S. S.; Stam, A.; Newburg, D. S. J. Nutr. 1994, 124, 2358.
9. (g) Gyorgy, P.; Jeanloz, R. W.; von Nicolai, H.; Zilliken, F. Eur. J. Biochem. 1974, 43, 29.
10. (h) Ofek, I.; Beachey, E. H. Adv. Intern. Med. 1980, 25, 503.
11. (i) Laegreid, A.; Otnaess, A. B. K.; Fuglesang, J. Pediatr. Res. 1986, 20, 416.
12. (j) Zopf, D.; Roth, S. Lancet 1996, 347, 1017.
13. (k) Cravioto, A.; Tello, A.; Villafan, H.; Ruiz, J.; Del Vedovo, S.; Neeser, J.-R. J. Infect. Dis. 1991, 163, 1247.
14. (l) Newburg, D. S.; Pickering, L. K.; McCluer, R. H.; Cleary, T. C. J. Infect. Dis. 1990, 162, 1075.
15. Coppa, G. V.; Gabrielli, O.; Giorgi, P.; Catassi, C.; Montanari, M. P.; Varaldo, P. E.; Nichols, B. L. Lancet 1990, 335, 569.
16. (a) Feizi, T. Nature 1985, 314, 53.
17. (b) Wieruszeski, J. M.; Chekkor, A.; Bouquelet, S.; Montreuil, J.; Strecker, G.; Peter-Katalinic, J.; Egge, H. Carbohydr. Res. 1985, 137, 127.
18. (c) Strecker, G.; Fievre, S.; Wieruszeski, J. M.; Michalski, J. C.; Montreuil, J. Carbohydr. Res. 1992, 226, 1.
19. (d) Dua, V. K.; Goso, K.; Dube, V. E.; Bush, C. A. J. Chromatogr. 1985, 328, 259.
20. (e) Yamashita, K.; Mizuochi, T.; Kobata, A. Methods Enzymol. 1982, 83, 105.
21. (a) Gopal, P. K.; Gill, H. S. Br. J. Nutr., Suppl. 1 2000, 84, S69.
22. (b) Sharon, N.; Ofek, I. Glycoconj. J. 2000, 17, 659.
23. (c) Boedeker, E. C. Gastroenterology 1982, 83, 489.
24. (a) Urashima, T.; Saito, T.; Nakamura, T.; Messer, M. Glycoconj. J. 2001, 18, 357.
25. (b) Messer, M.; Urashima, T. Trends Glycosci. Glycotechnol. 2002, 14, 153.
26. (c) Guerardel, Y.; Morelle, W.; Plancke, Y.; Lemoine, J.; Strecker, G. Carbohydr. Res. 1999, 320, 230.
27. (d) Saksena, R.; Deepak, D.; Khare, A.; Sahai, R.; Tripathi, L. M.; Srivastava, V. M. L. Biochem. Biophys. Acta 1999, 1428, 433.
28. (e) Chaturvedi, P.; Sharma, C. B. Biochim. Biophys. Acta 1988, 967, 115.
29. (f) Urashima, T.; Bubb, W. A.; Messer, M.; Tsuji, Y.; Taneda, Y. Carbohydr. Res. 1994, 262, 173.
30. Nakamura, T.; Urashima, T. Trends Glycosci. Glycotechnol. 2004, 16, 135.
31. Meijer, A.; Ellervik, U. J. Org. Chem. 2004, 69, 6249.
32. Yashunsky, D. U.; Higson, A. P.; Ross, A. J.; Nikolaev, A. V. Carbohydr. Res. 2001, 336, 243.
33. Berces, A.; Whitfield, D. M.; Nukada, T.; Santos, I. Z.; Obuchowska, A.; Krepinsky, J. J. Can. J. Chem. 2004, 82, 1157.
34. Fried, J.; Walz, D. E. J. Am. Chem. Soc. 1949, 71, 140.
35. Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 212, 277.
36. (a) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
37. (b) Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
38. Agnihotri, G.; Misra, A. K. Tetrahedron Lett. 2006, 47, 3653.
39. Schmidt, R. R.; Jung, K.-H. Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997, 283-312.
40. (a) Hasegawa, A.; Kiso, M. In Carbohydrates - Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H.; Hasegawa, A.; Suami, T., Eds.; Wiley: New York, 1992, 243-266.
41. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997, 357-379.
42. (c) Boons, G.-J.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539.
43. (d) Kanie, O.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1988, 7, 501.
44. (e) Paulsen, H.; Tietz, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 927.
45. (f) Hasegawa, A.; Nagahama, T.; Ohki, T.; Hotta, K.; Ishida, H.; Kiso, M. J. Carbohydr. Chem. 1991, 10, 493.
46. (g) Kiso, M.; Ando, K.; Inagaki, H.; Ishida, H.; Hasegawa, A. Carbohydr. Res. 1995, 272, 159.
47. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998.
48. (i) Iida, M.; Endo, A.; Fujita, S.; Numata, M.; Sugimoto, M.; Nunomura, S.; Ogawa, T. J. Carbohydr. Chem. 1998, 17, 647.
49. Pearlman, W. M. Tetrahedron Lett. 1967, 8, 1663.