Synthesis and evaluation of amino-threoses in d- and l-series: Are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 12, 2007, Pages 4125-4135

  Chevrier, Carine ^a   Defoin, Albert ^a   Tarnus, Céline ^a  

^a Ecole Nationale Superieure de Chimie de Mulhouse   (France)

Author keywords

Aminosugars; Aminothreose; Glycosidase inhibition

Indexed keywords

4 AMINOTHREOSE; ALPHA GLUCOSIDASE; ALPHA MANNOSIDASE; AMINOSUGAR; DEXTRO 4 AMINOTHREOSE; ETHYL DEXTRO TARTRATE; ETHYL LEVO TARTRATE; GLYCOSIDASE INHIBITOR; TARTARIC ACID; TETROSE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG BINDING; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION;

AMINO SUGARS; ENZYME INHIBITORS; GLYCOSIDE HYDROLASES; MAGNETIC RESONANCE SPECTROSCOPY; TETROSES;

EID: 34247637664     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.03.073     Document Type: Article

References (70)

1. Sinnott M.E. Chem. Rev. 90 (1990) 1171-1202
2. Elbein A.D. Ann. Rev. Biochem. 56 (1987) 497-534
3. Niwa T., Inouye S., Tsuruoka T., Koaze Y., and Niida T. Agric. Biol. Chem. 34 (1970) 966-968
4. Reese E.T., Parrish F.W., and Ettlinger M. Carbohydr. Res. 18 (1971) 381-388
5. Legler G., and Jülich E. Carbohydr. Res. 128 (1984) 61-72
6. Kodama Y., Tsuruoka T., Niwa T., and Inouye Sh. J. Antibiot 38 (1985) 116-118
7. Ishida N., Kumagai K., Niida T., Hamamoto K., and Shomura T. J. Antibiot., Ser A 20 (1967) 62-65
8. Ishida N., Kumagai K., Niida T., Tsuruoka T., and Yumoto H. J. Antibiot., Ser A 20 (1967) 66-71
9. Niwa T., Tsuruoka T., Goi H., Kodama Y., Itoh J., Inouye Sh., Yamada Y., Niida T., Nobe M., and Ogawa Y. J. Antibiot. 37 (1984) 1579-1586
10. Legler G., and Pohl St. Carbohydr. Res. 155 (1986) 119-129
11. Miyake Y., and Ebata M. Agric. Biol. Chem. 52 (1988) 1649-1654
12. Inouye Sh., Tsuruoka T., Ito T., and Niida T. Tetrahedron 23 (1968) 2125-2144
13. Shibata T., Nakayama O., Tsurumi Y., Okuhara M., Terano H., and Kohsaka M. J. Antibiot. 41 (1988) 296-301
14. Kim Y.J., Takatsuki A., Kogoshi N., and Kitahara T. Tetrahedron 55 (1999) 8353-8364
15. Kayakiri H., Nakamura K., Takase Sh., Setoi H., Uchida I., Terano H., Hashimoto M., Tada T., and Koda Sh. Chem. Pharm. Bull. 39 (1991) 2807-2812
16. Behr J.-B., Chevrier C., Defoin A., Tarnus C., and Streith J. Tetrahedron 59 (2003) 543-553
17. Ballini R., Marcantoni E., and Petrini M. J. Org. Chem. 57 (1992) 1316-1318
18. McCaig A.E., Meldrum K.P., and Wightman R.H. Tetrahedron 54 (1998) 9429-9446
19. Murray R.W., Iyanar K., Chen J.-X., and Wearing J.T. J. Org. Chem. 61 (1996) 8099-8102
20. Cicchi S., Höld I., and Brandi A. J. Org. Chem. 58 (1993) 5274-5275
21. Brandi, A.; Cardona, Fr.; Cicchi, S.; Cordero, M.; Goti, A. Current Trend in Organic Synthesis 1999, Scolastico & Nicotra Ed., Academic/Plenum Publishers, pp. 213-220.
22. Cordero Fr.M., Cicchi S., Goti A., and Brandi A. Tetrahedron Lett. 35 (1994) 949-952
23. Dulphy H., Gras J.-L., and Lejon T. Tetrahedron 52 (1996) 8517-8524
24. Fuji K., Nakano Sh., and Fujita E. Synthesis (1975) 276-277
25. Iida H., Yamazaki N., and Kiyabashi Ch. J. Org. Chem. 51 (1986) 1069-1073
26. Goti A., Cicchi S., Cacciarini M., Cardona Fr., Fedi V., and Brandi A. Eur. J. Org. Chem. (2000) 3633-3645
27. Cicchi S., Goti A., and Brandi A. J. Org. Chem. 60 (1995) 4743-4778
28. Stevens J.D., and Fletcher Jr. H.G. J. Org. Chem. 33 (1968) 1799-1805
29. Behr J.-B., Defoin A., Mahmood N., and Streith J. Helv. Chim. Acta 78 (1995) 1166-1177
30. Paulsen H., Leupold F., and Todt K. Liebigs Ann. Chem. 692 (1966) 200-214
31. Paulsen H., and Leupold F. Chem. Ber. 102 (1969) 2822-2834
32. Iida H., Yamazaki N., and Kibayashi Ch. J. Org. Chem. 52 (1987) 3337-3342
33. Chida N., Furuno Y., Ikemoto H., and Ogawa S. Carbohydr. Res. 237 (1992) 185-194
34. Cardona Fr., Goti A., Picasso S., Vogel P., and Brandi A. J. Carbohydr. Chem. 19 (2000) 585-601
35. Joubert M., Defoin A., Tarnus C., and Streith J. Synlett (2000) 1366-1368
36. Fleet G.W.J., Nicholas S.J., Smith P.W., Evans S.V., Fellow L.E., and Nash R.J. Tetrahedron Lett. 26 (1985) 3127-3130
37. Legler G. Adv. Carbohydr. Chem. Biochem. 48 (1990) 319-384
38. Hughes A.B., and Rudge A.J. Nat. Prod. Reports (1994) 135-162
39. Zechel D.L., and Withers S.G. Acc. Chem. Res. 33 (2000) 11-18
40. Some piperidine amino-sugars are likely an equilibrium mixture between α-anomer, β-anomer and imine form, this later form being in low but measurable amounts:. Defoin A., Sarazin H., and Streith J. Tetrahedron 53 (1997) 13783-13796
41. Dubernet M., Defoin A., and Tarnus C. Bioorg. Med. Chem. Lett. 16 (2006) 1172-1174
42. Frandsen T.P., Palcic M.H., and Swensson B. Eur. J. Biochem. 269 (2002) 728-734
43. Davies G., and Henrissat B. Structure 3 (1995) 853-859
44. Henrissat B. Biochem. Soc. Trans. 26 (1998) 153-156
45. Vasella A., Davies J.G., and Böhm M. Curr. Opin. Chem. Biol. 6 (2002) 619-629
46. Czjzek M., Cicek M., Zamboni V., Bevan D.R., Henrissat B., and Esen A. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 13555-135560
47. Verdoucq L., Morinière J., Bevan D.R., Esen A., Vasella A., Henrissat B., and Czjzek M. J. Biol. Chem. 279 (2004) 31796-31803
48. Golubev A.M., Nagem R.A.P., Brandão Neto J.R., Neustroev K.N., Eneyskaya E.V., Kulminskaya A.A., Shabalin K.A., Savel'ev A.N., and Polikarpov I. J. Mol. Biol. 339 (2004) 413-422
49. Fujimoto Z., Kaneko S., Momma M., Kobayashi H., and Mizuno H. J. Biol. Chem. 278 (2003) 20313-20318
50. Sulzenbacher G., Bignon Ch., Nishimura T., Tarling Ch.A., Withers S.G., Henrissat B., and Bourne Y. J. Biol. Chem. 279 (2004) 13119-13128
51. Czjzek M., Cicek M., Zamboni V., Burmeister W.P., Bevan D.R., Henrissat B., and Esen A. Biochem. J. 354 (2001) 37-46
52. Dale M.P., Ensley H.E., Kern K., Sastry K.A.R., and Byers L.D. Biochemistry 24 (1985) 3530-3539
53. Bourne Y., and Henrissat B. Curr. Opin. Struct. Biol. 11 (2001) 593-600
54. Snaith S.M. Biochem. J. 147 (1975) 83-90
55. Howard S., He Sh., and Withers S.G. J. Biol. Chem. 23 (1998) 2067-2072
56. van den. Elsen J.M.H., Kuntz D.A., and Rose D.R. EMBO J. 20 (2001) 3008-3017
57. Vallée F., Lipari F., Yip P., Sleno B., Herscovics A., and Howell P.L. EMBO J. 19 (2000) 581-588
58. Vallée F., Karaweg Kh., Herscovics A., Moremen K.W., and Howell P.L. J. Biol. Chem. 275 (2000) 41287-41298
59. Karaweg Kh., Siriwardena A., Tempels W., Liu Zh.-J., Glushka J., Wang B.-Ch., and Moremen K.W. J. Biol. Chem. 280 (2005) 16197-16207
60. Swiss-Prot P38158 and P53341.
61. He Sh., and Withers S.G. J. Biol. Chem. 272 (1997) 24864-24867
62. Winkler D.A., and Holan G. J. Med. Chem. 32 (1989) 2084-2089
63. Ichikawa Y., Igarashi Y., Ichikawa M., and Suhara Y. J. Am. Chem. Soc. 120 (1998) 3007-3018
64. Bernotas R.C., Papandreou G., Urbach J., and Ganem B. Tetrahedron Lett. 31 (1990) 3393-3396
65. Blanco M.-J., and Sardina F.J. J. Org. Chem. 63 (1998) 3411-3416
66. Wang Y.-F., Takaoka Y., and Wong Ch.-H. Angew. Chem. 106 (1994) 1343-1345
67. Angew. Chem. Int. Ed. Engl. 33 (1994) 1242-1244
68. Ly H.D., Howard S., Shum K., He Sh., Zhu A., and Withers S.G. Carbohydr. Res. 329 (2000) 539-547
69. Andrews P.R., Craik D.J., and Martin J.L. J. Med. Chem. 27 (1984) 1648-1657
70. Sifferlen Th., Defoin A., Streith J., Le Nouën D., Tarnus C., Dosbaâ I., and Foglietti M.-J. Tetrahedron 56 (2000) 971-978