메뉴 건너뛰기




Volumn 120, Issue 13, 1998, Pages 3007-3018

1-N-Iminosugars: Potent and selective inhibitors of β-glycosidases

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYNOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN DERIVATIVE; 1 N IMINOCARBOHYDRATE DERIVATIVE; CARBOHYDRATE DERIVATIVE; GLYCOSIDASE; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0032495792     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973443k     Document Type: Article
Times cited : (232)

References (50)
  • 2
    • 0001094662 scopus 로고    scopus 로고
    • (b) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 13
    • 0014377791 scopus 로고
    • For reviews on the synthesis of DNJ-based iminosugar inhibitor, see: (a) Paulsen, H.; Todt, K. Adv. Carbohydr. Chem. Biochem. 1968, 23, 115-232. (b) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190. (c) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340-347. (d) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (e) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432 and 521-546.
    • (1968) Adv. Carbohydr. Chem. Biochem. , vol.23 , pp. 115-232
    • Paulsen, H.1    Todt, K.2
  • 14
    • 1542763243 scopus 로고
    • For reviews on the synthesis of DNJ-based iminosugar inhibitor, see: (a) Paulsen, H.; Todt, K. Adv. Carbohydr. Chem. Biochem. 1968, 23, 115-232. (b) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190. (c) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340-347. (d) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (e) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432 and 521-546.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 182-190
    • Look, G.C.1    Fotsch, C.H.2    Wong, C.-H.3
  • 15
    • 0001367771 scopus 로고    scopus 로고
    • For reviews on the synthesis of DNJ-based iminosugar inhibitor, see: (a) Paulsen, H.; Todt, K. Adv. Carbohydr. Chem. Biochem. 1968, 23, 115-232. (b) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190. (c) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340-347. (d) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (e) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432 and 521-546.
    • (1996) Acc. Chem. Res. , vol.29 , pp. 340-347
    • Ganem, B.B.1
  • 16
    • 2642642035 scopus 로고    scopus 로고
    • For reviews on the synthesis of DNJ-based iminosugar inhibitor, see: (a) Paulsen, H.; Todt, K. Adv. Carbohydr. Chem. Biochem. 1968, 23, 115-232. (b) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190. (c) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340-347. (d) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (e) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432 and 521-546.
    • (1996) Chem. Rev. , vol.96 , pp. 443-473
    • Gijsen, H.J.M.1    Qiao, L.2    Fitz, W.3    Wong, C.-H.4
  • 17
    • 0029109703 scopus 로고
    • For reviews on the synthesis of DNJ-based iminosugar inhibitor, see: (a) Paulsen, H.; Todt, K. Adv. Carbohydr. Chem. Biochem. 1968, 23, 115-232. (b) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190. (c) Ganem, B. B. Acc. Chem. Res. 1996, 29, 340-347. (d) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443-473. (e) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412-432 and 521-546.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 412-432
    • Wong, C.-H.1    Halcomb, R.L.2    Ichikawa, Y.3    Kajimoto, T.4
  • 18
    • 0029095922 scopus 로고
    • For some potent designed glycosidase inhibitors, see: (a) Heightman, T. D.; Ermert, P.; Klein, D.; Vasella, A. Helv. Chim. Acta 1995, 78, 514-532. (b) Pan, Y.-T.; Kanshal, G. P.; Papandreou, G.; Ganem, B.; Elbein, A. D. J. Biol. Chem. 1992, 267, 8313-8318.
    • (1995) Helv. Chim. Acta , vol.78 , pp. 514-532
    • Heightman, T.D.1    Ermert, P.2    Klein, D.3    Vasella, A.4
  • 19
    • 0026739335 scopus 로고
    • For some potent designed glycosidase inhibitors, see: (a) Heightman, T. D.; Ermert, P.; Klein, D.; Vasella, A. Helv. Chim. Acta 1995, 78, 514-532. (b) Pan, Y.-T.; Kanshal, G. P.; Papandreou, G.; Ganem, B.; Elbein, A. D. J. Biol. Chem. 1992, 267, 8313-8318.
    • (1992) J. Biol. Chem. , vol.267 , pp. 8313-8318
    • Pan, Y.-T.1    Kanshal, G.P.2    Papandreou, G.3    Ganem, B.4    Elbein, A.D.5
  • 20
    • 33845471322 scopus 로고
    • For reviews on the reaction mechanims of glycosidase reactions, see: (a) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305-311. (b) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047-1077. (c) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (d) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
    • (1984) Acc. Chem. Res. , vol.17 , pp. 305-311
    • Kirby, A.J.1
  • 21
    • 1542545189 scopus 로고
    • For reviews on the reaction mechanims of glycosidase reactions, see: (a) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305-311. (b) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047-1077. (c) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (d) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
    • (1987) Chem. Rev. , vol.87 , pp. 1047-1077
    • Gorenstein, D.G.1
  • 22
    • 0025675652 scopus 로고
    • For reviews on the reaction mechanims of glycosidase reactions, see: (a) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305-311. (b) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047-1077. (c) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (d) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
    • (1990) Adv. Carbohydr. Chem. Biochem. , vol.48 , pp. 319-384
    • Legler, G.1
  • 23
    • 11944256494 scopus 로고
    • For reviews on the reaction mechanims of glycosidase reactions, see: (a) Kirby, A. J. Acc. Chem. Res. 1984, 17, 305-311. (b) Gorenstein, D. G. Chem. Rev. 1987, 87, 1047-1077. (c) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (d) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
    • (1990) Chem. Rev. , vol.90 , pp. 1171-1202
    • Sinnott, M.L.1
  • 30
    • 0029645404 scopus 로고
    • (b) Davies, G. Structure 1995, 3, 853-859.
    • (1995) Structure , vol.3 , pp. 853-859
    • Davies, G.1
  • 37
    • 0024596071 scopus 로고
    • (a) For study of N-alkylated iminosugars with isolated enzymes, see: Al Daher, S.; Fleet, G.; Namgoong, S. K.; Winchester, B. Biochem. J. 1989, 258, 613-615. (b) For study of N-alkylated iminosugars with cells, see: Tan, A.; van den Broek, L.; van Boeckel, S.; Ploegh, H.; Bolscher, J. J. Biol. Chem. 1991, 266, 14504-14510.
    • (1989) Biochem. J. , vol.258 , pp. 613-615
    • Al Daher, S.1    Fleet, G.2    Namgoong, S.K.3    Winchester, B.4
  • 38
    • 0026350737 scopus 로고
    • (a) For study of N-alkylated iminosugars with isolated enzymes, see: Al Daher, S.; Fleet, G.; Namgoong, S. K.; Winchester, B. Biochem. J. 1989, 258, 613-615. (b) For study of N-alkylated iminosugars with cells, see: Tan, A.; van den Broek, L.; van Boeckel, S.; Ploegh, H.; Bolscher, J. J. Biol. Chem. 1991, 266, 14504-14510.
    • (1991) J. Biol. Chem. , vol.266 , pp. 14504-14510
    • Tan, A.1    Van Den Broek, L.2    Van Boeckel, S.3    Ploegh, H.4    Bolscher, J.5
  • 45
    • 0025287439 scopus 로고
    • We synthesized the iminosugars 62 and 63 from 24 which was a synthetic intermediate for the galactose-type 1-N-iminosugar 12. Their syntheses have been reported. For 62: (a) Bernotas, R. C.; Papandreous, G.; Urbach, J.; Ganem, B. Tetrahedron Lett. 1990, 31, 3393-3396. (b) See ref 24. For 63: McCaig, A. E.; Chomier, B.; Wightman, R. H. J. Carbohydr. Chem. 1994, 13, 397-407.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3393-3396
    • Bernotas, R.C.1    Papandreous, G.2    Urbach, J.3    Ganem, B.4
  • 46
    • 21344496106 scopus 로고
    • We synthesized the iminosugars 62 and 63 from 24 which was a synthetic intermediate for the galactose-type 1-N-iminosugar 12. Their syntheses have been reported. For 62: (a) Bernotas, R. C.; Papandreous, G.; Urbach, J.; Ganem, B. Tetrahedron Lett. 1990, 31, 3393-3396. (b) See ref 24. For 63: McCaig, A. E.; Chomier, B.; Wightman, R. H. J. Carbohydr. Chem. 1994, 13, 397-407.
    • (1994) J. Carbohydr. Chem. , vol.13 , pp. 397-407
    • McCaig, A.E.1    Chomier, B.2    Wightman, R.H.3
  • 48
    • 0001733374 scopus 로고
    • (b) An unsuccessful approach to a similar amidine derivative was reported: Bird, P.; Dolphin, D. H.; Withers, S. G. Can. J. Chem. 1990, 68, 317-322.
    • (1990) Can. J. Chem. , vol.68 , pp. 317-322
    • Bird, P.1    Dolphin, D.H.2    Withers, S.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.