Concentration dependence of glycosylation outcome: A clue to reproducibility and understanding the reasons behind

European Journal of Organic Chemistry

Volumn , Issue 10, 2012, Pages 1926-1934

  Kononov, Leonid O ^a   Malysheva, Nelly N ^a   Orlova, Anna V ^a   Zinin, Alexander I ^a   Laptinskaya, Tatiana V ^b   Kononova, Elena G ^c   Kolotyrkina, Natalya G ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Aggregation; Glycosylation; Sialic acids; Stereoselectivity

Indexed keywords

EID: 84858791123     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201101613     Document Type: Article

References (60)

1. R. Schauer, Biochemistry of Sialic Acid Diversity, in: Carbohydrates in Chemistry and Biology, part II, Biology of Saccharides, vol. 3, Biosynthesis and Degradation of Glycoconjugates (Eds.:, B. Ernst, G. W. Hart, P. SinaA), Wiley-VCH, Weinheim, Germany, 2000, pp. 227-244.
2. T. Angata, A. Varki, Chem. Rev. 2002, 102, 439-469.
3. A. Varki, Nature 2007, 446, 1023-1029.
4. G.-J. Boons, A. V. Demchenko, Chem. Rev. 2000, 100, 4539-4565.
5. D. K. Ress, R. J. Linhardt, Curr. Org. Synth. 2004, 1, 31-46.
6. H. Ando, A. Imamura, Trends Glycosci. Glycotechnol. 2004, 16, 293-303.
7. C. DeMeo, in: Frontiers in Modern Carbohydrate Chemistry (Ed.:, A. V. Demchenko), ACS Symposium Series 960, American Chemical Society, Washington, DC, 2007, pp. 118-131.
8. C. De Meo, U. Priyadarshani, Carbohydr. Res. 2008, 343, 1540-1552.
9. H. Ando, Trends Glycosci. Glycotechnol. 2008, 20, 141-158.
10. S. Hanashima, Trends Glycosci. Glycotechnol. 2011, 23, 111-121.
11. D. Crich, J. Org. Chem. 2011, 76, 9193-9209.
12. Y. Uchinashi, M. Nagasaki, J. Zhou, K. Tanaka, K. Fukase, Org. Biomol. Chem. 2011, 9, 7243-7248, and references cited therein
13. K.-C. Chu, C.-T. Ren, C.-P. Lu, C.-H. Hsu, T.-H. Sun, J.-L. Han, B. Pal, T.-A. Chao, Y.-F. Lin, S.-H. Wu, C.-H. Wong, C.-Y. Wu, Angew. Chem. Int. Ed. 2011, 50, 9391-9395, and references cited therein
14. B. N. Harris, P. P. Patel, C. P. Gobble, M. J. Stark, C. De Meo, Eur. J. Org. Chem. 2011, 4023-4027, and references cited therein.
15. D. Crich, B. Wu, Org. Lett. 2008, 10, 4033-4035, and references cited therein.
16. A. A. Sherman, O. N. Yudina, B. S. Komarova, Y. E. Tsvetkov, S. Iacobelli, N. E. Nifantiev, Synthesis 2005, 1783-1788.
17. S. Hanashima, B. Castagner, D. Esposito, T. Nokami, P. H. Seeberger, Org. Lett. 2007, 9, 1777-1779, and references cited therein.
18. L. O. Kononov et al., unpublished results.
19. For an example of the successful use of multivariative experimental design for the optimization of glycosylation, see:, F. Stazi, G. Palmisano, M. Turconi, S. Clini, M. Santagostino, J. Org. Chem. 2004, 69, 1097-1103.
20. L. O. Kononov, N. N. Malysheva, E. G. Kononova, O. G. Garkusha, Russ. Chem. Bull. 2006, 55, 1311-1313.
21. L. O. Kononov, N. N. Malysheva, E. G. Kononova, A. V. Orlova, Eur. J. Org. Chem. 2008, 3251-3255.
22. L. O. Kononov, N. N. Malysheva, A. V. Orlova, Eur. J. Org. Chem. 2009, 611-616, and references cited therein
23. A. V. Orlova, L. O. Kononov, B. G. Kimel, I. B. Sivaev, V. I. Bregadze, Appl. Organomet. Chem. 2006, 20, 416-420.
24. This term has recently been coined to describe stereoisomerism at the supramolecular level (in the crystal):, M. Czugler, N. Bathori, CrystEngComm 2004, 6, 494-503.
25. Y.-J. Wang, J. Jia, Z.-Y. Gu, F.-F. Liang, R.-C. Li, M.-H. Huang, C.-S. Xu, J.-X. Zhang, Y. Men, G.-W. Xing, Carbohydr. Res. 2011, 346, 1271-1276.
26. A. V. Orlova, A. M. Shpirt, N. Y. Kulikova, L. O. Kononov, Carbohydr. Res. 2010, 345, 721-730.
27. Optical rotation was shown to be a highly sensitive tool for probing the state of solution, see:, L. O. Kononov, D. E. Tsvetkov, A. V. Orlova, Russ. Chem. Bull. 2002, 51, 1337-1338.
28. S. M. Wilson, K. B. Wiberg, M. J. Murphy, P. H. Vaccaro, Chirality 2008, 20, 357-369.
29. M.-R. Goldsmith, N. Jayasuriya, D. N. Beratan, P. Wipf, J. Am. Chem. Soc. 2003, 125, 15696-15697.
30. M. Suarez, N. Branda, J.-M. Lehn, A. Decian, J. Fischer, Helv. Chim. Acta 1998, 81, 1-13.
31. H. Tanaka, M. Adachi, T. Takahashi, Chem. Eur. J. 2005, 11, 849-862.
32. Pure Appl. Chem. 1996, 68, 1919-2008.
33. J.-R. Pougny, P. SinaA, Tetrahedron Lett. 1976, 17, 4073-4076.
34. R. R. Schmidt, E. Rücker, Tetrahedron Lett. 1980, 21, 1421-1424.
35. T. Murase, A. Kameyama, K. P. R. Kartha, H. Ishida, M. Kiso, A. Hasegawa, J. Carbohydr. Chem. 1989, 8, 265-283.
36. A. J. Ratcliffe, B. Fraser-Reid, J. Chem. Soc. Perkin Trans. 1 1990, 747-750.
37. R. R. Schmidt, M. Behrendt, A. Toepfer, Synlett 1990, 694-696.
38. J. Braccini, C. Derouet, J. Esnault, C. H. de Penhoat, J.-M. Mallet, V. Michon, P. SinaA, Carbohydr. Res. 1993, 246, 23-41.
39. H. G. Bazin, Y. Du, T. Polat, R. J. Linhardt, J. Org. Chem. 1999, 64, 7254-7259.
40. Y. J. Lee, K. Lee, E. H. Jung, H. B. Jeon, K. S. Kim, Org. Lett. 2005, 7, 3263-3266.
41. S. Hanashima, K. Sato, Y. Ito, Y. Yamaguchi, Eur. J. Org. Chem. 2009, 4215-4220.
42. A. V. Kornilov, A. A. Sherman, L. O. Kononov, A. S. Shashkov, N. E. Nifant′ev, Carbohydr. Res. 2000, 329, 717-730.
43. N. M. Spijker, C. A. A. van Boeckel, Angew. Chem. 1991, 103, 179;
44. Angew. Chem. Int. Ed. Engl. 1991, 30, 180-183.
45. L. Bohe, D. Crich, Trends Glycosci. Glycotechnol. 2010, 22, 1-15, and references cited therein.
46. B. Chu, Laser Light Scattering: Basic Principles and Practice, Academic Press, Boston, MA, 1991, p. 343.
47. B. J. Berne, R. Pecora, Dynamic Light Scattering with Applications to Chemistry, Biology, and Physics, Dover, New York, 2000, p. 376.
48. P. Rota, P. Allevi, R. Mattina, M. Anastasia, Org. Biomol. Chem. 2010, 8, 3771-3776.
49. D. M. Whitfield, Adv. Carbohydr. Chem. Biochem. 2009, 62, 83-159.
50. L. K. Mydock, A. V. Demchenko, Org. Biomol. Chem. 2010, 8, 497-510.
51. L. Bohe, D. Crich, C. R. Chim. 2011, 14, 3-16.
52. C.-S. Chao, C.-W. Li, M.-C. Chen, S.-S. Chang, K.-K. T. Mong, Chem. Eur. J. 2009, 15, 10972-10982.
53. For a typical example, see:, C. Liu, M. R. Richards, T. L. Lowary, J. Org. Chem. 2010, 75, 4992-5007.
54. H. Satoh, H. S. Hansen, S. Manabe, W. F. van Gunsteren, P. H. Hünenberger, J. Chem. Theory Comput. 2010, 6, 1783-1797, and references cited therein.
55. B. Davis, J. Chem. Soc. Perkin Trans. 1 2000, 2137-2160.
56. M. A. Sierra, M. C. de la Torre, Angew. Chem. 2000, 112, 1628;
57. Angew. Chem. Int. Ed. 2000, 39, 1538-1559.
58. M. A. Sierra, M. C. de la Torre, Dead Ends and Detours: Direct Ways to Successful Total Synthesis, Wiley-VCH, Weinheim, Germany, 2004, p. 290.
59. H. Hori, T. Nakajima, Y. Nishida, H. Ohrui, H. Meguro, Tetrahedron Lett. 1988, 29, 6317-6320.
60. S. Prytulla, J. Lauterwein, M. Klessinger, J. Thiem, Carbohydr. Res. 1991, 215, 345-349.