Glycoprotein Processing Inhibitors
Abdelmjid Ossor
Search for more papers by this authorAlan D. Elbein
Search for more papers by this authorAbdelmjid Ossor
Search for more papers by this authorAlan D. Elbein
Search for more papers by this authorProf. Dr. Beat Ernst
Institut für Molekulare Pharmazie, Universität Basel, Klingenbergstrasse 50, 4051 Basel, Switzerland
Search for more papers by this authorProf. Dr. Gerald W. Hart
Dept. of Biological Chemistry, Johns Hopkins University School of Medicine, 725 N. Wolf St. Rm., 401 Hunterian Baltimore, MD 21205-2185, USA
Search for more papers by this authorProf. Dr. Pierre Sinaý
Dept. de Chimie, URA 1686, Ecole Normale Supérieure, 24 rue Lhomond, 75231 Paris Cedex 05, France
Search for more papers by this authorProf. Dr. Beat Ernst
Institut für Molekulare Pharmazie, Universität Basel, Klingenbergstrasse 50, 4051 Basel, Switzerland
Search for more papers by this authorProf. Dr. Gerald W. Hart
Dept. of Biological Chemistry, Johns Hopkins University School of Medicine, 725 N. Wolf St. Rm., 401 Hunterian Baltimore, MD 21205-2185, USA
Search for more papers by this authorProf. Dr. Pierre Sinaý
Dept. de Chimie, URA 1686, Ecole Normale Supérieure, 24 rue Lhomond, 75231 Paris Cedex 05, France
Search for more papers by this authorSummary
The prelims comprise:
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Introduction
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Structural Classification
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Distribution of Glycosidase Inhibitors in the Plant Kingdom
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Isolation and Structural Determination
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Glycosidase Inhibitory Activity
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Structure-Activity Relationships
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N-Linked Oligosaccharide Processing
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Inhibitors of N-Linked Oligosaccharide Processing
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Summary and Future Prospects
References
- Colegate, S.M., Dorling, P.R. and Huxtable, C.R. (1979) Aust. J. Chem. 32, 2257–2264.
- Hohenschutz, L.D., Bell, E.A., Jewess, P.J., Leworthy, D.P., Pryce, R.J., Arnold, E. and Clardy, J. (1981) Phytochemistry 20, 811–814.
- Kite, G.C., Horn, J.M., Romeo, J.T., Fellows, L.E., Lees, D.C., Scofield, A.M., and Smith, N.G. (1990) Phytochemistry 29, 103–105.
- Goldman, A., Milat, M., Ducrot, P.H., Lallemand, J.Y., Maill, M., Lepingle, A., Charpin, I. and Tepfer, D. (1990) Phytochemistry 29, 2115–2127.
- Evans, E.V., Fellows, L.E., Shing, T.K.M., Fleet, G.W.J. (1985) Phytochemistry 24, 1953–1955.
- Legler, G. and Julich, E. (1984) Carbohyd. Res. 128, 61–72.
- Molyneux, R.J., Benson, M., Wong, R.Y., Tropea, J.E. and Elbein, A.D. (1988) J. Nat. Prod. 51, 1198–1206.
- Molyneux, R.J., Pan, Y.T., Goldmann, A., Tepfer, D.A. and Elbein, A.D. (1993) Arch. Bio-chem. Biophys. 304, 81–88.
- Asano, N., Kato, A., Oseki, K., Kizu, H. and Matsui, K. (1995) Eur. J. Biochem. 229, 369–376.
- Evans, E.V., Fellows, L.E., Shing, T.K. and Fleet G.W.J., (1985) Phytochemistry 24, 1953–1955.
- Fellows, L., Doherty, C.H., Horn, J.M., Kite, G.C., Nash, R.J., Romeo, J.T., Simmonds, M.S.J, and Scofield, A.M. (1989) in “ Swainsonine and Related Glycosidase Inhibitors”, pp. 396–416, ( L.F. James, A.D. Elbein, R.J. Molyneux and CD. Warren, eds.), Iowa St. Univ. Press, Ames, IO.
- Stahr, H.M. and Martin, P.J. (1989) in “ Swainsonine and Related Glycosidase Inhibitors”, pp. 118–124, Iowa St. Univ. Press, Ames, IO.
- Molyneux, R.J. (1993) Meth. Plant Biochem. Vol 8, 511–530 ( P.G. Waterman, Ed), Academic Press, NY)
- Dorling, P.R., Huxtable, C.R. and Colegate, S.M. (1980) Biochem. J. 191, 649–652.
- Saul, R., Chambers, J.P., Molyneux, R.J., and Elbein, A.D. (1983) Arch. Biochem. Biophys. 221, 593–597.
- Saul, R., Molyneux, R.J. and Elbein, A.D. (1984) Arch. Biochem. Biophys. 230, 668–675.
- Pan, Y.T., Hori, H., Saul, R., Sanford, B.A., Molyneux, R.J. and Elbein, A.D. (1983) Biochemistry 22, 3975–3984.
- Trombetta, E.S., Simons, J.F. and Helenius, A. (1996) J. Biol. Chem. 271, 27509–27516.
- Szumilo, T. and Elbein, A.D. (1985) Anal. Biochem. 151, 32–40.
- Stutz, A. (1999) in “ Iminosugars as Glycosidase Inhibitors”, pp. 158–187. ( A. Stutz, ed), Wiley-VCH, Weinheim, FRG.
- Tyler, P.C. and Winchester, B.O. (1999) in “ Iminosugars as Glycosidase Inhibitors”, pp. 125–156. ( A. Stutz, ed.) Wiley-VCH, Weinheim, FRG.
- Ducrot, P-H. and Lallemand, J.Y. (1990) Tetrahedron Lett. 31, 3879–3882.
- Winkler, D.A. and Holan, G. (1989) J. Med. Chem. 32, 2084–2089.
- Winkler, D.A. (1996) J. Med. Chem. 39, 4332–4334.
- Asano, N., Kato, A., Miyauchi, M., Kizu, H., Tomimori, T., Matsui, K., Nash, R.J. and Molyneux, R.J. (1997) Eur. J. Biochem. 248, 296–303.
- Ebner, M., Ekhart, C.E. and Stutz, A. (1997) in “ Electronic Conference on Heterocyclic Chemistry 96”, ( H.S. Rzepa, J. Snyder, and C. Leach, eds.), Royal Society of Chemistry, London.
- Legler, G. (1973) Cell. Biochem. 2, 31–38.
- Dale, M.P., Ensley, H.E., Kern, K., Sastry, K. and Byers, L.D. (1985) Biochemistry 24, 3530.
- Hubbard, S.C. and Ivatt, R.J. (1981) Annu. Rev. Biochem. 50, 555–583.
- Snider, M. (1984) in “ Biology of Carbohydrates”, ( V. Ginsberg and P.W. Robbins, eds.) Vol. 2, pp. 163–198, Wiley and Sons, NY.
- Moreman, K.W., Trimble, R.B. and Herscovics, A. (1994) Glycobiology 4, 113–126.
- Katz-Fuller, B., Bieberich, E. and Bause, E. (1995) Eur. J. Biochem. 231, 344–351.
- Brada, D., Kerjaschki, D. and Roth, J. (1990) J. Cell. Biol. 110, 309–318.
- Bischoff, J., Liscum, L. and Kornfeld, R. (1986) J. Biol. Chem. 261, 4766–4774.
- Lai, A., Pang, P., Kalelkar, S., Romero, P.A., Herscovics, A. and Moreman, K.W. (1998) Glycobiology 8, 981–995.
-
Tulsiani, D.P.R. and
Touster, O.
(1988)
J. Biol. Chem.
254,
5408–5417.
10.1016/S0021-9258(18)60732-X Google Scholar
- Bieberich, E., Tremi, K., Volker, C., Rolfs, A., Katz-Fuller, B. and Bause, E. (1997) Eur. J. Biochem. 246, 681–689.
- Schachter, H. (1986) Biochem. Cell. Biochem. 64, 163–181.
- Yip, B., Chen, S.H., Mulder, H., Hoppner, J.M. and Schachter, H. (1997) Biochem. J. 321, 465–472.
- Herscovics, A. (1999) in “ Comprehensive Natural Products Chemistry”, ( B.M. Pinto, ed.), Vol. 3, Chapter 1. Elsevier Press, NY.
- Moreman, K.W., Touster, O. and Robbins, P.W. (1991) J. Biol. Chem. 252, 3227–3233.
- Kaushal, G.P., Szumilo, T., Pastuszak, I. and Elbein, A.D. (1990) Biochemistry 29, 2168–2176.
- Misago, M., Liao, Y.-F., Kudo, S., Eto, S., Mattei, M-G., Moreman, K.W. and Fukuda, M.N. (1995) Proc. Natl Acad. Sci. USA 92, 11766–11770.
- Tulsiani, D.P.R. and Touster, O. (1985) J. Biol. Chem. 260, 13081–13087.
- Monis, E., Bonay, P. and Hughes, R.C. (1987) Eur. J. Biochem. 168, 287–294.
- Bonay, P. and Hughes, R.C. (1991) Eur. J. Biochem. 197, 229–238.
- Tulsiani, D.P.R., Skudlarek, M.D. and Orgebin-Crist, M.C. (1989) J. Cell Biol. 109, 1257–1267.
- Herscovics, A. (1999) Biochim. Biophys. Acta 1426, 275–285.
- Spiro, R.G. (1994) in “ Guidebook to the Secretory Pathway” ( J. Rothblatt, P. Novick, and T. Stevens, eds.) pp. 188–189, Oxford press.
- Karaivanova, V.K., Luan, P. and Spiro, R.G. (1998) Glycobiology 6, 861–868.
- Kornfeld, R. and Kornfeld, S. (1985) Annu. Rev. Biochem. 54, 631–664.
- Beyer, T.A., Sadler, J.E., Rearick, J.L., Paulson, J.C. and Hill, R.L. (1981) Adv. Enzymol. 52, 23–175.
- Fukuda, M., Bierhuizen, M.F.A. and Nakayama, J. (1996) Glycobiology 6, 683–689.
- Rhinehart, B.L., Liu, P.S. and Robinson, K.M. (1989) in “ Swainsonine and Related Glycosidase Inhibitors” ( L.F. James, A.D. Elbein, R.J. Molyneux and C.D. Warren, eds.) pp. 279–290, Iowa St. Univ. Press, Ames, IO.
- Saul, R., Ghidoni, J.J., Molyneux, R.J. and Elbein, A.D. (1985) Proc. Natl Acad. Sci. USA 82, 93–97.
- Chen, Y.T. and Burchell, A. (1995) in “ The Metabolic and Molecular Basis of Inherited Diseases”, ( C.R. Scriver, A.L. Beaudet, W.S. Sly and D. Valle, eds.) McGraw-Hill, Inc. NY.
- Romero, P.A., Friedlander, P. and Herscovics, A. (1985) FEBS Lett. 83, 29–32.
- Elbein, A.D., Mitchell, M., Sanford, B.A., Fellows, L.E. and Evans, S.V. (1984) J. Biol. Chem. 259, 12409–12415.
- Tropea, J.E., Molyneux, R.J., Kaushal, G.P., Pan, Y.T., Mitchell, M. and Elbein, A.D. (1989) Biochemistry 28, 2027–2034.
- Ando, O., Satake, H., Itoi, K., Sato, A., Nakajima, M., Takahashi, S., Haruyama, H., Ohkuma, Y., Kinoshita, T. and Enokita, R. (1991) J. Antibiot. 44, 1165–1168.
- Zeng, Y-C. and Elbein, A.D. (1998) Arch. Biochem. Biophys. 355, 26–34.
- Liu, P.S. (1987) J. Org. Chem. 52, 4717–4721.
- Rhinehart, B.L., Robinson, K.M., Liu, P.S., Payne, A.J., Wheatley, M.E. and Wagner, S.R. (1987) J. Pharmacol. Exp. Ther. 241, 915–921.
- Kaushal, G.P., Pan, Y.T., Tropea, J.E., Mitchell, M., Liu, P. and Elbein, A.D. (1988) J. Biol. Chem. 263, 17278–17283.
- Elbein, A.D. (1991) FASEB J. 5, 3055–3063.
- Lodish, H. and Kong, N. (1984) J. Cell Biol. 98, 1720–1729.
- Edwards, E.H., Sprague, E.A., Kelley, J.L., Kerbacher, J.J., Schwartz, C.J. and Elbein, A.D. (1989) Biochemistry 28, 7679–7687.
- Arakai, R.F., Hedo, J.A., Collier, E. and Gordon, P. (1987) J. Biol. Chem. 262, 11886–11892.
- Montefiori, D.C., Robinson, W.E. Jr. and Mitchell, W.M. (1988) Proc. Natl Acad. Sci. USA 85, 9248–9252.
- Hammond, C., Braakman, I. and Helenius, A. (1994) Proc. Natl Acad. Sci. USA 91, 913–917.
- Van Leeuwen, J.E.M. and Kearse, K.P. (1997) /. Biol. Chem. 272, 4179–4186.
- Ware, F.E., Vassilakos, A., Peterson, P.A., Jackson, M.R., Lehrman, M.A. and Williams, D.B. (1995) J. Biol. Chem. 270, 4697–4704.
- Hebert, D.N., Foellmer, B. and Helenius, A. (1995) Cell 81, 425–433.
- Hammond, C. and Helenius, A. (1995) Curr. Opin. Cell Biol. 4, 523–529.
- Trombetta, S.E. and Parodi, A.J. (1992) J. Biol. Chem. 267, 9236–9240.
- Fernandez, F., Jannatipour, M., Hellman, U., Rokeach, L.A. and Parodi, A. (1996) EMBO J. 15, 705–713.
- Merkle, R.K., Elbein, A.D. and Heifetz, A. (1985) J. Biol. Chem. 260, 1083–1089.
- Kang, M.S. and Elbein, A.D. (1983) Plant Physiol. 71, 551–554.
- Elbein, A.D., Solf, R., Dorling, P.R. and Vosbeck, K. (1981) Proc. Natl Acad. Sci. USA 78, 7393–7397.
- Elbein, A.D., Vosbeck, K., Dorling, P. and Horisberger, M. (1982) J. Biol. Chem. 257, 1573–1576.
- Tulsiani, D.P.R., Broquist, H, and Tousler, O. (1985) Arch. Biochem. Biophys. 236, 427–434.
- Stegelmeier, B.L., Molyneux, R.J., Elbein, A.D. and James, L.P. (1995) Vet. Pathol. 32, 289–298.
- Fuhrmann, V., Bause, E., Legler, G. and Ploegh, H. (1984) Nature 307, 755–758.
- Fellows, L.E., Bell, E.A., Lynn, D.G., Pilkiewicz, F., Miura, I. and Nakanishi, J. (1979) J. Chem. Soc. Chem. Commun. 22, 977–978.
- Elbein, A.D., Legler, G., Tlusty, A., McDowell, W. and Schwarz, R. (1984) Arch. Biochem. Biophys. 235, 579–588.
- Gross, V., Steube, K., Tran-Thi, A., McDowell, W. and Schwarz, R. (1985) Eur. J. Biochem. 150, 41–46.
- Chin, D.J., Luskey, K.L., Anderson, R.G., Faust, J.R., Goldstein, J.L. and Brown, M.S. (1982) Proc. Natl Acad. Sci. USA 79, 1185–1189.
- Bischoff, J., Liscum, L. and Kornfeld, R. (1986) J. Biol. Chem. 261, 4766–4774.
- Snider, M.D. and Rogers, O.C. (1986) J. Cell Biol. 103, 265–275.
- Palamarczyk, G., Mitchell, M., Smith, P.W., Fleet, G.W.J, and Elbein, A.D. (1985) Arch. Biochem. Biophys. 243, 35–45.
- Pan, Y.T., Kaushal, G.P., Ganem, B. and Elbein, A.D. (1992) J. Biol. Chem. 267, 8313–8318.
- Kayakiri, H., Takese, S., Shibata, T., Okamoto, M., Terano, H., Hashimoto, M., Tada, T. and Koda, S. (1989) J. Org. Chem. 54, 4015–4016.
- Elbein, A.D., Tropea, J.E., Mitchell, M. and Kaushal, G.P. (1990) J. Biol. Chem. 265, 15599–15605.
- Chung, K.M., Shepard, V.L. and Stahl, P. (1984) J. Biol. Chem. 259, 14637–14641.
- Schwartz, P. and Elbein, A.D. (1985) J. Biol. Chem. 260, 14452–14458.
- Goss, P.E., Reid, C.L., Bailey, D. and Dennis, J.W. (1997) Clin. Cancer Res. 3, 1077–1086.
- Tropea, J.E, Kaushal, G.P., Pastuszak, I., Mitchell, M., Aoyagi, T., Molyneux, R.J. and Elbein, A.D. (1990) Biochemistry 29, 10062–10069.
- Varki, A. (1997) Glycobiology 3, 97–130.
- Stanley, P. (1992) Glycobiology 2, 99–107.