Synthesis of new hexosaminyl D- and L-chiro-inositols related to putative insulin mediators

European Journal of Organic Chemistry

Volumn , Issue 18, 2003, Pages 3505-3514

  Cid, M Belén ^b   Bonilla, Julia B ^a   Alfonso, Francisco ^a   Martin Lomas, Manuel ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Carbohydrates; Cyclitols; Glycosylations; Oligosaccharides

Indexed keywords

DEXTRO GALACTO 2 AZIDO 2 DEOXYTRICHLOROACETIMIDATE GLYCOSYL; DEXTRO GLUCO 2 AZIDO 2 DEOXYTRICHLOROACETIMIDATE GLYCOSYL; HEXOSAMINYLINOSITOL DERIVATIVE; INOSITOL DERIVATIVE; INSULIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; GLYCOSYLATION; REACTION ANALYSIS; SIGNAL TRANSDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0141727853     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300252     Document Type: Article

References (44)

1. [1a] N. Khiar, M. Martín-Lomas, in: Carbohydrate Mimics. Concepts and Methods (Ed.: Y. Chapleur), Wiley VCH, 1998, pp. 433-462 and references therein.
2. [1b] H. Dietrich, J. F. Espinosa, J. L. Chiara, J. Jimé nez-Barbero, Y. León, I. Varela-Nieto, J. M. Mato, F. H. Cano, C. Foces-Foces, M. Martín-Lomas, Chem. Eur. J. 1999, 5, 320-335.
3. [1c] M. Martín-Lomas, M. Flores-Mosquera, N. Khiar, Eur. J. Org. Chem. 2000, 1539-1545.
4. [1d] M. Martín-Lomas, M. Flores-Mosquera, J. L. Chiara, Eur. J. Org. Chem. 2000, 1547-1561.
5. [1e] M. Martín-Lomas, N. Khiar, S. García, J. L. Koessler, P. M. Nieto, T. W. Rademacher, Chem. Eur. J. 2000, 6, 3608-3621.
6. [1f] M. Martín-Lomas, P. M. Nieto, N. Khiar, S. García, M. Flores-Mosquera, E. Poirot, J. Angulo, J. L. Muñoz, Tetrahedron: Asymmetry 2000, 11, 37-51.
7. [1g] M. B. Cid, J. B. Bonilla, S. Dumarcay, F. Alfonso, M. Martin-Lomas, Eur. J. Org. Chem. 2002, 881-888.
8. [1h] J. B. Bonilla, J. L. Muñoz-Ponce, P. M. Nieto, M. B. Cid, M. Martín-Lomas, Eur. J. Org. Chem. 2002, 889-898.
9. [2a] I. Varela-Nieto, Y. León, H. N. Caro, Comp. Biochem. Physiol. 1996, 115, 223-241.
10. [2b] P. Stralförs, BioEssays 1997, 19, 327-335.
11. [2c] M. C. Field, Glycobiology 1997, 7, 161-168.
12. [2d] D. P. Jones, I. Varela-Nieto, Int. J. Biochem. Cell. Biol. 1998, 30, 313-336.
13. [2e] D. P. Jones, I. Varela-Nieto, Mol. Med. 1999, 5, 505-514.
14. [3a] J. M. Mato, K. L. Kelly, A. Abler, L. Jarret, B. E. Corkey, J. A. Cashell, D. Zopf, Biochem. Biophys. Res. Commun. 1987, 146, 746-770.
15. [3b] J. Larner, L. C. Huang, C. F. W. Schwartz, A. S. Oswald, T. Y. Shen, M. Kinter, G. Tang, K. Zeller, Biochem. Biophys. Res. Commun. 1988, 151, 1416-1426.
16. [3c] H. N. Caro, S. Kunjara, T. W. Rademacher, D. R. Jones, M. A. Avila, I. Varela-Nieto, Biochem. Mol. Med. 1997, 61, 214-218.
17. [4a] G. Romero, G. Gómez, L. C. Huang, K. Lilley, L. Lutrell, Proc. Natl. Acad. Sci. USA 1990, 87, 1476-1480.
18. [4b] J. Represa, M. A. Avila, C. Miner, F. Giraldez, G. Romero, J. M. Mato, I. Varela-Nieto, Proc. Natl. Acad. Sci. USA 1991, 88, 8016-8019.
19. [4c] J. Represa, M. A. Avila, G. Romero, J. M. Mato, F. Giraldez, I. Varela-Nieto, Dev. Biol. 1993, 159, 257-265.
20. [4d] J. Larner, L. C. Huang, C. F. W. Schwartz, A. S. Oswald, T. Y. Shen, M. Kinter, G. Tang, K. Zeller, Biochem. Biophys. Res. Commun. 1988, 151, 1416-1426.
21. [4e] Y. Pak, J. Larner, Biochem. Biophys. Rev. Commun. 1992, 184, 1042-7.
22. [4f] J. M. Mato, K. L. Kelly, A. Abler, L. Jarret, B. E. Corkey, J. A. Cashel, D. Zopf, Biochem. Biophys. Res. Commun. 1987, 146, 764-770.
23. [4g] Y. Pak, C. R. Paule, C. R. Bao, L. C. Huang, J. Larner, Proc. Natl. Acad. Sci. USA 1992, 90, 7759-7763.
24. T. W. Rademacher, H. N. Caro, M. Martín-Lomas, Y. León, I. Varela-Nieto, Patent Cooperation Treaty (PCT) GB98/03847, 1998.
25. K. S. Bruzik, in: Carbohydrates in Drug Design (Eds.: Z. J. Witzak, K. A. Nieforth), Marcel Dekker, New York, 1997, pp. 385-431.
26. K. S. Bruzik, A. A. Haakeem, M. D. Tsai, Biochemistry 1994, 33, 8367-8374.
27. R. Taguchi, J. Yamazaki, Y. Tsutsui, H. Ikezawa, Arch. Biochem. Biophys. 1997, 342, 161-168.
28. [9a] G. Anikumar, L. G. Nair, B. Fraser-Reid, Org. Lett. 2000, 2, 2587-2589.
29. [9b] B. Fraser-Reid, J. C. López, K. V. Radhakrishanan, M. Mach, U. Schlueter, A. Gómez, C. Uriel, Can. J. Chem. 2002, 80, 1075-1087.
30. [9c] A. Vasella, Bioorganic Chemistry: Carbohydrates (Ed: S. M. Hecht), Oxford University Press, New York, 1999, chapter 2.
31. [10a] S. J. Angyal, R. M. Hoskinson, Methods Carbohydr. Chem. 1963, 2, 87-XXXX.
32. [10b] J. J. Kiddle, Chem. Rev. 1995, 95, 2189.
33. [11a] R. R. Schmidt, W. Kinzy, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
34. [11b] A. Vasella, C. Witzig, J. L. Chiara, M. Martín-Lomas, Helv. Chim. Acta 1991, 74, 2073-2077.
35. [11c] P. B. Alper, S. C. Hung, C. H. Wong, Tetrahedron Lett. 1996, 37, 6029-6032.
36. D. Urban, T Skydstrup, J.-M. Beau, J. Org. Chem. 1998, 63, 2507-2516.
37. G. Grundler, R. R. Schmidt, Liebigs Ann. Chem. 1984, 11, 1826-1847.
38. Mono-acetonide 11 has been prepared previously by different methods. [14a] C. E. Ballou, H. O. L. Fisher, J. Am. Chem. Soc. 1953, 75, 3673-3675.
39. [14b] M. Mandel, T. Hudlicky, J. Chem. Soc., Perkin. Trans. 1. 1993, 741-743.
40. [14c] T. Hudlicky, M. Mandel, J. Rouden, R. S. Lee, B. Bachmann, T. Dudding, K. J. Yost, J. S. Merola, J. Chem. Soc., Perkin. Trans. #?# 1994, 1, 1553-1568. {{βAuthor: Perkin Trans. 1 or 2?}}.
41. Bis-acetonide 12 has been described. See: G. F. Painter, A. Falsaw, J. Chem. Soc., Perkin Trans. 1 2000, 1157.
42. Diol 14 has been prepared previously. See: [16a] Z. J. Jia, L. Olsson, B. Fraser-Reid, J. Chem. Soc., Perkin Trans. 1 1998, 631-632.
43. [16b] A. Kornienko, G. Marnera, M. d'Alarcao, Carbohydr. Res. 1998, 310, 141-144.
44. K. K. Reddy, J. R. Falk, J. Kapdevilla, Tetrahedron Lett. 1993, 34, 7869-7872.