Design and synthesis of selenonium and sulfonium ions related to the naturally occurring glucosidase inhibitor salacinol

Canadian Journal of Chemistry

Volumn 84, Issue 10, 2006, Pages 1351-1362

  Liu, Hui ^a   Pinto, B Mario ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

Cyclic sulfates; D gulonic lactone; Glycosidase inhibitors; L ascorbic acid; Selenonium salts; Sulfonium salts; Zwitterionic

Indexed keywords

CYCLIC SULFATES; D-GULONIC-Γ-LACTONE; GLYCOSIDASE INHIBITORS; L-ASCORBIC ACID; SELENONIUM SALTS; SULFONIUM SALTS; ZWITTERIONIC;

ENZYME INHIBITION; GLUCOSE; OLIGOSACCHARIDES; SULFUR; SYNTHESIS (CHEMICAL);

SELENIUM COMPOUNDS;

1,4 ANHDYRO 2,3,5,6 DI O ISOPROPYLLIDENE 1 [2',4' BENZYLIDENEDIOXY 3' (SUFOOXY)BUTYL]SULFONIO]DEXTRO ALLITOL; 1,4 ANHYDRO 1 [2',4' DIHYDROXY 3' (SUFOOXY)BUTYL]SELENONIO]DEXTRO ALLITOL; 1,4 ANHYDRO 1 [2',4' DIHYDROXY 3' (SUFOOXY)BUTYL]SELENONIO]LEVO ALLITOL; 1,4 ANHYDRO 1 [2',4' DIHYDROXY 3' (SUFOOXY)BUTYL]SULFONIO]LEVO ALLITOL; 1,4 ANHYDRO 1 [2',4' DIHYDROXY 3' (SULOOXY)BUTYL]SULFONIO]DEXTRO ALLITOL; 1,4 ANHYDRO 1 [2',4',5',6' TETRAHYDROXY 3' (SUFOOXY)HEXYL]SELENONIO'DEXTRO ALLITOL; 1,4 ANHYDRO 1 [2',4',5',6' TETRAHYDROXY 3' (SUFOOXY)HEXYL]SELENONIO]LEVO ALLITOL; 1,4 ANHYDRO 1 [2',4',5',6' TETRAHYDROXY 3' (SUFOOXY)HEXYL]SULFONIO]DEXTRO ALLITOL; 1,4 ANHYDRO 1 [2',4',5',6' TETRAHYDROXY 3' (SUFOOXY)HEXYL]SULFONIO]LEVO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLDINE 1 [2',4' BENZYLIDENEDIOXY 5',6' ISOPROPYLIDENEDIOXY 3' (SUFOOXY)HEXYL]SELENONIO]LEVO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 1 [2',4 BENZYLIDENEDIOXY 3' (SUFOOXY)BUTYL]SELENONIO]DEXTRO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 1 [2',4 BENZYLIDENEDIOXY 3' (SUFOOXY)BUTYL]SELENONIO]LEVO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 1 [2',4' BENZYLIDENEDIOXY 3' (SUFOOXY)BUTYL]SULFONIO LEVO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 1 [2',4' BENZYLIDENEDIOXY 5',6' ISOPROPYLIDENEDIOXY 3' (SUFOOXY)HEXYL]SELENONIO]DEXTRO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 1 [2',4' BENZYLIDENEDIOXY 5',6' ISOPROPYLIDENEDIOXY 3' (SUFOOXY)HEXYL]SULFONIO]DEXTRO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 1 [2',4' BENZYLIDENEDIOXY 5',6' ISOPROPYLIDENEDIOXY 3' (SUFOOXY)HEXYL]SULFONIO]LEVO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 4 SELENO DEXTRO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 4 SELENO LEVO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 4 THIO DEXTRO ALLITOL; 1,4 ANHYDRO 2,3,5,6 DI O ISOPROPYLIDENE 4 THIO LEVO ALLITOL; 2,3,5,6 DI O ISOPROPYLIDENE 1,4 DI O METHANESULFONYL LEVO GULITOL; 2,3,5,6, DI O ISOPROPYLIDENE 1,4 DI O METHANESULFONYL DEXTRO GULITOL; AMPHOLYTE; GLYCOSIDASE INHIBITOR; SALACINOL; SELENONIUM; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DEPROTECTION REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 33847613853     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-100     Document Type: Article

References (46)

1. (a) B. Winchester and G.W.J. Fleet. Glycobiology, 2, 199 (1992);
2. (b) J.F. Kennedy and C.A. White. Bioactive carbohydrates in chemistry, biochemistry, and biology. Halsted Press, New York. 1983;
3. (c) F. Garcia-Olmeda, G. Salcedo, R. Sanchez-Monge, L. Gomez, L. Royo, and P. Carbonero. Oxford Surv. Plant Molecular Cell Biol. 4, 275 (1987);
4. (d) C. Bompard-Gilles, P. Rousseau, P. Rouge, and F. Payan. Structure, 4, 1441 (1996);
5. (e) F. Vallee, A. Kadziola, Y. Bourne, M. Juy, K.W. Rodenburg, B. Svensson, and R. Haser. Structure, 6, 649 (1998);
6. (f) S. Strobl, K. Maskos, G. Wiegand, R. Huber, F-X. GomisRuth, and R. Glockshuber. Structure, 6, 911 (1998).
7. (a) A. Varki, R. Cummings, J. Esko, H. Freeze, G. Hart, and J. Marth (Editors). Essentials of glycobiology. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY. 1999;
8. (b) A.D. Elbein, R.J. Molyneux and B.M. Pinto (Editors). Comprehensive natural products chemistry. Vol. 3. Elsevier, Oxford, UK. 1999. Chap. 7;
9. (c) N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet. Tetrahedron: Asymmetry, 11, 1645 (2000);
10. (d) J.D. McCarter and S.G. Withers. Curr. Opin. Struct. Biol. 4, 885 (1994);
11. (e) H.D. Ly and S.G. Withers. Annu. Rev. Biochem. 68, 487 (1999).
12. R.R. Holman, C.A. Cull, and R.C. Turner. Diabetes Care, 22, 960 (1999).
13. G.S. Jacob. Curr. Opin. Struct. Biol., 5, 605 (1995).
14. L. Sherwood. Fundamentals of physiology. 2nd ed. West Publishing Co., New York, NY. 1995. p. 517.
15. (a) M.L. Sinnott. Chem. Rev. 90, 1171 (1990);
16. (b) T.D. Henghman, A.T. Vasella. Angew. Chem. Int. Ed. 38, 750 (1999).
17. (a) D. Zechel and S.G. Withers. Acc. Chem. Res. 33, 11 (2000);
18. (b) C.S. Rye and S.G. Withers. Curr. Opin. Chem. Biol. 4, 573 (2000).
19. (a) K. Schoffling and I. Hillebrand. Dtsch. Med. Wochenschr. 106, 1083 (1981);
20. (b) J.L. Chiasson, R.G. Josse, A.H. Hunt, C. Palmason, N.W. Roger, S.A. Ross, E.A. Ryan, M.H. Tan, and T.M.S. Wolever. Ann. Intern. Med. 121, 928 (1994).
21. (a) T. Kobatake, Y. Matsuzawa, K. Tokunaga, S. Fujioka, T. Kawamoto, Y. Keno, H. Odaka, T. Matsuo, and S. Tarui. Int. J. Obesity, 13, 147 (1989);
22. (b) T. Matsuo, H. Odaka, and H. Ikeda. Am. J. Clin. Nutr. 55, 3145 (1992);
23. (c) R.R. Holman, C.C. Cull, and R.C. Tyrner. Diabetes Care, 21, 256 (1998).
24. M. Yoshikawa, T. Murakami, H. Shimada, H. Matsuda, J. Yamahara, G. Tanabe, and O. Muraoka. Tetrahedron Lett. 38, 8367 (1997).
25. M. Yoshikawa, T. Murakami, K. Yashiro, and H. Matsuda. Chem. Pharm. Bull. 46, 1339 (1998).
26. M. Yoshikawa, T. Murikawa, H. Matsuda, G. Tanabe, and O. Muraoka. Bioorg. Med. Chem. 10, 1547 (2002).
27. H. Yuasa, J. Takada, and H. Hashimoto. Tetrahedron Lett. 41, 6615 (2000).
28. A. Ghavami, B.D. Johnston, and B.M. Pinto. J. Org. Chem. 66, 2312 (2001).
29. A. Ghavami, K.S. Sadalapure, B.D. Johnston, M. Lobera, B.B. Snider, and B.M. Pinto. Synlett, 1259 (2003).
30. A. Ghavami, B.D. Johnston, M.D. Maddess, S.M. Chinapoo, M.T. Jensen, B. Svensson, and B.M. Pinto. Can. J. Chem. 80, 937 (2002).
31. B.D. Johnston, A. Ghavami, M.T. Jensen, B. Svensson, and B.M. Pinto. J. Am. Chem. Soc. 124, 8245 (2002).
32. (a) H. Liu and B.M. Pinto. J. Org. Chem. 70, 753 (2005);
33. (b) B.M. Pinto, B.D. Johnston, A. Ghavami, M.G. Szczepina, H. Liu, and K. Sadalapure. US Patent 06 455 573, 24 September 2002.
34. (a) A. Ghavami, B.D. Johnston, M.T. Jensen, B. Svensson, and B.M. Pinto. J. Am. Chem. Soc. 123, 6268 (2001);
35. (b) O. Muraoka, S. Ying, K. Yoshikai, Y. Matsuura, E. Yamada, T. Minematsu, G. Tanabe, H. Matsuda, and M. Yoshikawa. Chem. Pharm. Bull. 49, 1503 (2001).
36. (a) M.G. Szczepina, B.D. Johnston, Y. Yuan, B. Svensson, and B.M. Pinto. J. Am. Chem. Soc. 126, 12458 (2004);
37. (b) E. Gallienne, M. Benazza, G. Demailly, J. Boite, and M. Lemaire. Tetrahedron, 61, 4557 (2005).
38. (a) B.D. Johnston, H.H. Hensen, and B.M. Pinto. J. Org. Chem. 71, 1111 (2005);
39. (b) H. Liu and B.M. Pinto. Can. J. Chem. 84, 497 (2006);
40. (c) H. Liu, L. Sim, D.R. Rose, and B.M. Pinto. J. Org. Chem. 71, 3007 (2006).
41. Y. Li, C.R. Scott, N.A. Chamoles, A. Chavami, B.M. Pinto, T. Frantisek, and M.H. Gelb. Clin. Chem. 50, 1785 (2004).
42. X. Wen, Y. Yuan, D.A. Kuntz, D.R. Rose, and B.M. Pinto. Biochemistry, 44, 6729 (2005).
43. D. Kuntz, A. Ghavami, B.D. Johnston, B.M. Pinto, and D.R. Rose. Tetrahedron: Asymmetry, 16, 25 (2005).
44. G.W.J. Fleet, N.G. Ramsden, and D.R. Witty. Tetrahedron, 45, 319 (1989).
45. L.S. Jeong, D.Z. Jin, H.O. Kim, D.H. Shin, H.R. Moon, P. Gunaga, M.W. Chun, Y.C. Kim, N. Melman, Z.G. Gao, and K.A. Jacobson. J. Med. Chem., 46, 3775 (2003).
46. G.C. Andrews, T.C. Crawford, and B.E. Bacon. J. Org. Chem. 46, 2976 (1981).