A paradigm case for the merging of glycal and enzymatic assembly methods in glycoconjugate synthesis: A highly efficient chemo-enzymatic synthesis of GM3

Chemistry - A European Journal

Volumn 2, Issue 11, 1996, Pages 1359-1362

  Liu, Kevin K C ^c   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Havemeyer Hall ^*  (United States)

^c PFIZER INC   (United States)

Author keywords

Anhydrosugars; Enzymatic catalysis; Gangliosides; Glycoconjugates; Glycosidations

Indexed keywords

ANHYDROSUGARS; ENZYMATIC CATALYSIS; GANGLIOSIDES; GLYCOCONJUGATES; GLYCOSIDATIONS;

CARBOHYDRATES; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

EID: 84891310170     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960021105     Document Type: Article

References (67)

1. New Comprehensive Biochemistry (Eds.: A. Neuberger; L. L. M. van Deenen), Vol. 10, Elsevier, Amsterdam, 1985, pp. 199-260.
2. P. H. Fishman, J. Membr. Biol. 1982, 69, 85.
3. a) H. Higashi, Y. Hirabayashi, Y. Fukui, M. Kaiki, M. Matsumoto, S. Ueda, S. Kato, Cancer Res. 1985, 45, 3796.
4. b) S. Hakomori, Ann. Rev. Immunol. 1984, 2, 103.
5. a) F. Ebel, E. Schmitt, J. Peter-Katalinic, B. Kniep, P. F. Muhlradt, Biochemistry 1992, 31, 12190.
6. b) T. Feizi, Nature 1985, 314, 53.
7. T. Taki, Y. Hirabayashi., H. Ishikawa, S. Ando, K. Kon, Y. Tanaka, M. Matsumoto, J. Biol. Chem. 1986, 261, 3075.
8. Y. Hirabayashi, A. Hyogo, T. Nakao, K. Tsuchiya, Y. Suzuki, M. Matsumoto, K. Kon, S. Ando, J. Biol. Chem. 1990, 265, 8144.
9. a) S. G. Malta, G. Yorke, F. J. Roisen, Develop. Brain Res. 1986, 27, 243.
10. b) R. W. Ledeen, J. Neurosci. Res. 1984, 12, 147.
11. J. S. Schneider, A. Pope, K. Simpson, J. Taggart, M. G. Smith, L. DiStefano, Science, 1992, 256, 843.
12. T. Yamakawa, S. Suzuki, J. Biochem. (Tokyo) 1952, 39, 383.
13. D. Bouhours, J.-F. Bouhours, J. Biol. Chem. 1991, 266, 12944.
14. a) E. Bremer, J. Schlessinger, S. Hakomori, J. Biol. Chem. 1986, 261, 2434.
15. b) N. Hanai, G. A. Nores, C.-R. Torres-mendez, S. Hakomori, Biochem. Biophys. Res. Commun. 1987, 147, 127.
16. a) J. M. Carubia, R. K. Yu, L. J. Macala, J. M. Kirkwood, J. M. Varga, Biochem. Biophys. Res. Commun. 1984, 120, 500.
17. b) J. Portoukalian, G. Zwingelstein, J.-F. Dore, J.-J. Borgoin, Biochemie 1976, 58, 1285.
18. a) K. Takahashi, K. Ono, Y. Hirabayashi, M. Taniguchi, J. Immunol. 1983, 78, 152.
19. b) K. Ono, Y. Hiraga, Y. Hirabayashi, M. Taniguchi, Cancer Res. 1988, 48, 2703.
20. S. Ando, H. Waki, K. Kon, Y. Kishimoto, in Gangliosides and Modulation of Neuronal Functions (Ed.: H. Rahmann), Springer, Heidelberg, 1987, pp. 167-177.
21. a) R. L. Halcomb, S.J. Danishefsky, J. Am. Chem. Soc. 1989, 111, 6661.
22. b) D. M. Gordon, S. J. Danishefsky, Carbohydr. Res. 1990, 111, 361.
23. c) D. B. Berkowitz, S. J. Danishefsky, G. K. Schulte, J. Am. Chem. Soc. 1992, 114, 4518.
24. For sialyfransferases in organic syntheses: a) S. Sabesan, J. C. Paulson, J. Am. Chem. Soc. 1986, 108, 2068.
25. b) J. Thiem, W. Treder, Angew. Chem. Int. Ed. Engl. 1986, 25, 1096.
26. c) E. S. Simon. M. D. Bednarski, G. M. Whitesides, J. Am. Chem. Soc. 1988, 110, 7159.
27. d) C. Unverzag, H. Kunz, J. C. Paulson, ibid. 1990, 112, 9308.
28. e) C. Auge, R. Fernandez-Fernandez, C. Gautheron, Carbohydr. Res. 1990, 200, 257.
29. f) Y. Ichikawa, G.-J. Shen., C.-H. Wong, J. Am. Chem. Soc. 1991, 113, 4698.
30. g) Y. Ichikawa, Y.-C. Lin, D. P. Dumas, G.-J. Shen, E. Garcia-Junceds, M. A. Williams, R. Bayer, C. Ketcham, L. E. Walker, J. C. Paulson, C.-H. Wong, ibid. 1992, 114, 9283.
31. h) A. Lubineau, C. Auge, P. Francois, Carbohydr. Res. 1992, 228, 137.
32. i) B. Guilbert, T. H. Khan, S. L. Flitsch, J. Chem. Soc. Chem. Commun. 1992, 1526.
33. k) Y. Ito, J. J. Gaudino, J. C. Paulson, Pure Appl. Chem. 1993, 65, 753.
34. For a similar approach using α-2.6-sialyltransferase from another independent group: B. Guilbert, S. L. Flitsch, J. Chem. Soc. Perkin. Trans. 1 1994, 1181.
35. K. K.-C. Liu, S. J. Danishefsky, J. Am. Chem. Soc. 1993, 115, 4933.
36. 3: a) M. Sugimoto, T. Ogawa, Glycocojugate J. 1985, 2, 5.
37. b) T. Murase, H. Ishida, M. Kiso, A. Hasegawa, Carbohydr. Res. 1989, 188, 71.
38. c) Y. Ito, J. C. Paulson, J. Am. Chem. Soc. 1993, 115, 1603.
39. W. N. Haworth, E. L. Hirst, M. M. T. Plant, R. J. W. Reynolds, J. Chem. Soc. 1930, 2644.
40. For the preparation of dimethyldioxirane: R. W. Murray, R. Jeyaraman, J. Org. Chem. 1985, 50, 2847.
41. For ceramides preparation: a) P. Zimmermann, R. R. Schmidt, Liebigs. Ann. Chem. 1988, 663.
42. b) K. C. Nicolaou, T. Caulfield, H. Kataoka, T. Kumazawa, J. Am. Chem. Soc. 1988, 110, 7910.
43. c) M. Kiso, A. Nakamura, Y. Tomita, A. Hasegawa, Carbohydr. Res. 1986. 158, 101.
44. d) K. Koike, M. Numata, M. Sugimoto, Y. Nakahara, T. Ogawa, ibid. 1986, 158, 113.
45. J. Gervay, J. M. Peterson, T. Oriyama, S. J. Danishefsky, J. Org. Chem. 1993, 58, 5465.
46. J. T. Randolph, S. J. Danishefsky, J. Am. Chem. Soc. 1993, 115, 8473.
47. a) T. Ogawa, M. Matsui, Tetrahedron 1981, 37, 2363.
48. b) S. David, S. Hanessian, ibid. 1985, 41, 643.
49. J. T. Randolph, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5693-5700.
50. M. T. Bilodeau, T. K. Park, S. Hu, J. T. Randolph, S. J. Danishefsky, P. O. Livingston, S. Zhang, J. Am. Chem. Soc. 1995, 117, 7840-41.
51. K. K.-C. Liu, S. J. Danishefsky, J. Org. Chem. 1994, 59, 1895-97.
52. a) A. Kameyama, H. Ishida, M. Kiso, A. Hasegawa Carbohydr. Res. 1990, 200, 269-285.
53. b) H. Prabhanjan, K. Aoyama, M. Kiso, A. Hasegawa, ibid. 1992, 233, 87-99.
54. c) M. Numata, M. Sugimoto, K. Koike, T. Ogawa, ibid. 1987, 163, 209-225.
55. d) A. Hasegawa, H. Ishida, M. Kiso, J. Carbohydr. Chem. 1990, 9, 181-199.
56. CMP-sialic acid is commercially available from Sigma and Genzyme Ltd.
57. J. I. Rearick, J. E. Sadler, J. C. Paulson, R. L. Hill, J. Biol. Chem. 1979, 254, 4444.
58. a) D. Shapiro in Chemistry of Sphingolipids, Hermann, Paris, 1969, p. 99.
59. b) P. Zimmermann, R. R. Schmidt, Angew. Chem. Int. Ed. Engl. 1986, 25, 725.
60. c) R. Bommer, R. R. Schmidt, Liebigs. Ann. Chem. 1989, 1107.
61. d) P. Zimmermann, R. Bommer, T. Bar, R. R. Schmidt, J. Carbohydr. Chem. 1988, 7, 435.
62. a) H. Kessler, A. Kling, M. Kottenhahm, Angew. Chem. Int. Ed. Engl. 1990, 29, 425.
63. b) J. Thiem, H. K. Schwentner, J. Schwentner, Synthesis 1978, 696.
64. a) S. J. Danishefsky, J. Gervay, J. M. Peterson, F. E. McDonald, K. Koseki, T. Oriyama, D. A. Griffith., C.-H. Wong, D. P. Dumas, J. Am. Chem. Soc. 1992, 114, 8329.
65. b) S. J. Danishefsky, K. Koseki, D. A. Griffith, J. Gervat, J. M. Peterson, F. E. McDonald, T. Oriyama, ibid. 1992, 114, 8331.
66. F. E. McDonald, S. J. Danishefsky, J. Org. Chem. 1992, 57, 7001.
67. For instance, the synthesis described herein, where the ceramide precursor is coupled through a 1,2-anhydrosugar, is much shorter than was possible by classical glycosylation [18]. The latter required in each case extensive manipulations to obtain the glycosyl donor.