-
1
-
-
0242287992
-
-
For recent leading reviews, see: (a) N. Asano, N. Glycobiology 2003, 13, 93R.
-
(2003)
Glycobiology
, vol.13
-
-
Asano, N.N.1
-
2
-
-
0037967286
-
-
(b) Greimel, P.; Spreitz, J.; Stütz, A. E.; Wrodnigg, T. M. Curr. Top. Med. Chem. 2003, 3, 513.
-
(2003)
Curr. Top. Med. Chem.
, vol.3
, pp. 513
-
-
Greimel, P.1
Spreitz, J.2
Stütz, A.E.3
Wrodnigg, T.M.4
-
3
-
-
0038170055
-
-
(c) Butters, T. M.; Dwek, R. A.; Platt, F. M. Curr. Top. Med. Chem. 2003, 3, 561.
-
(2003)
Curr. Top. Med. Chem.
, vol.3
, pp. 561
-
-
Butters, T.M.1
Dwek, R.A.2
Platt, F.M.3
-
4
-
-
0036802905
-
-
(d) Vasella, A.; Davies, G. J.; Böhm, M. Curr. Opin. Chem. Biol. 2002, 6, 619.
-
(2002)
Curr. Opin. Chem. Biol.
, vol.6
, pp. 619
-
-
Vasella, A.1
Davies, G.J.2
Böhm, M.3
-
5
-
-
0033559148
-
-
(e) Heightman, T. D.; Vasella, A. Angew. Chem., Int. Ed. 1999, 38, 750.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 750
-
-
Heightman, T.D.1
Vasella, A.2
-
8
-
-
84900403742
-
-
Although the term "azasugar" is widely used in the literature to refer to glycomimetics where the endocyclic oxygen atom has been replaced by nitrogen, the term is not strictly correct according to the IUPAC-IUMB nomenclature recommendations for carbohydrates, the accepted term being "iminosugar". "Azahexose" would actually imply that a carbon atom has been exchanged for a nitrogen atom. See: McNaught, A. D. Pure Appl. Chem. 1996, 68, 1919.
-
(1996)
Pure Appl. Chem.
, vol.68
, pp. 1919
-
-
McNaught, A.D.1
-
9
-
-
0037832251
-
-
For recent reviews on iminosugar glycosidase inhibitors, see: (a) Asano, N. Curr. Top. Med. Chem. 2003, 3, 471.
-
(2003)
Curr. Top. Med. Chem.
, vol.3
, pp. 471
-
-
Asano, N.1
-
10
-
-
0036462605
-
-
(b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515.
-
(2002)
Chem. Rev.
, vol.102
, pp. 515
-
-
Lillelund, V.H.1
Jensen, H.H.2
Liang, X.3
Bols, M.4
-
11
-
-
0035925104
-
-
(c) Watson, A. A.; Fleet, G. W. J.; Asano, N.; Molyneux, R. J.; Nash, R. J. Phytochemistry 2001, 56, 265.
-
(2001)
Phytochemistry
, vol.56
, pp. 265
-
-
Watson, A.A.1
Fleet, G.W.J.2
Asano, N.3
Molyneux, R.J.4
Nash, R.J.5
-
12
-
-
0034607947
-
-
(d) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645.
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 1645
-
-
Asano, N.1
Nash, R.J.2
Molyneux, R.J.3
Fleet, G.W.J.4
-
13
-
-
0000584109
-
Alkaloid Glycosidase Inhibitors
-
Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford
-
(e) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129.
-
(1999)
Comprehensive Natural Products Chemistry
, vol.3
, pp. 129
-
-
Elbein, A.D.1
Molyneux, R.J.2
-
14
-
-
0002237552
-
Taxonomic Distribution of Iminosugars in Plants and Their Biological Activities
-
Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany
-
(f) Simmonds, M. S. J.; Kite, G. C.; Porter, E. A. Taxonomic Distribution of Iminosugars in Plants and Their Biological Activities. In Iminosugars as Glycosidase Inhibitors; Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 8.
-
(1999)
Iminosugars as Glycosidase Inhibitors
, pp. 8
-
-
Simmonds, M.S.J.1
Kite, G.C.2
Porter, E.A.3
-
15
-
-
84961353103
-
Glycoprotein Processing Inhibitors
-
Ernst, B., Hart, G. W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, Germany
-
(g) Ossor, A.; Elbein, A. D. Glycoprotein Processing Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, Germany, 2000; Part II, Vol. 3, p 513.
-
(2000)
Carbohydrates in Chemistry and Biology
, vol.3
, Issue.PART II
, pp. 513
-
-
Ossor, A.1
Elbein, A.D.2
-
16
-
-
0000986987
-
Toward Azaglycosyl Compounds and Homoazaglycosides
-
Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany
-
(a) Martin, O. R. Toward Azaglycosyl Compounds and Homoazaglycosides. In Carbohydrate Mimics. Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany, 1998; p 259.
-
(1998)
Carbohydrate Mimics. Concepts and Methods
, pp. 259
-
-
Martin, O.R.1
-
17
-
-
0028905327
-
-
(b) Wong, C.-H-; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1492
-
-
Wong, C.-H.1
Provencher, L.2
Porco Jr., J.A.3
Jung, S.-H.4
Wang, Y.-F.5
Chen, L.6
Wang, R.7
Steensma, D.H.8
-
18
-
-
0001214733
-
-
Evans, S. V.; Fellows, L. E.; Shing, T. K. M.; Fleet, G. W. J. Phytochemistry 1985, 24, 1953.
-
(1985)
Phytochemistry
, vol.24
, pp. 1953
-
-
Evans, S.V.1
Fellows, L.E.2
Shing, T.K.M.3
Fleet, G.W.J.4
-
19
-
-
0024245410
-
-
(a) Molyneux, R. J.; Benson, M.; Wong, R. Y.; Tropea, J. E.; Elbein, A. D. J. Nat. Prod. 1988, 51, 1198-1206.
-
(1988)
J. Nat. Prod.
, vol.51
, pp. 1198-1206
-
-
Molyneux, R.J.1
Benson, M.2
Wong, R.Y.3
Tropea, J.E.4
Elbein, A.D.5
-
20
-
-
0037423121
-
-
(b) Kato, A.; Kano, E.; Adachi, I.; Molyneux, R. J.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Wormald, M. R.; Kizu, H.; Ikeda, K.; Asano, N. Tetrahedron: Asymmetry 2003, 14, 325.
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 325
-
-
Kato, A.1
Kano, E.2
Adachi, I.3
Molyneux, R.J.4
Watson, A.A.5
Nash, R.J.6
Fleet, G.W.J.7
Wormald, M.R.8
Kizu, H.9
Ikeda, K.10
Asano, N.11
-
21
-
-
0002022599
-
Azasugars: Chemistry and Their Biological Activity as Potential Anti-HIV Drugs
-
Witczak, Z. J., Nieforth, K. A., Eds.; Marcel Dekker: New York
-
van den Broek, L. A. G. M. Azasugars: Chemistry and Their Biological Activity as Potential Anti-HIV Drugs. In Carbohydrates in Drug Design; Witczak, Z. J., Nieforth, K. A., Eds.; Marcel Dekker: New York, 1997; p 471.
-
(1997)
Carbohydrates in Drug Design
, pp. 471
-
-
Van Den Broek, L.A.G.M.1
-
22
-
-
2442422859
-
-
note
-
2 character, typically a pseudoamide-type nitrogen.
-
-
-
-
23
-
-
0035900338
-
-
(a) García-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2001, 66, 7604.
-
(2001)
J. Org. Chem.
, vol.66
, pp. 7604
-
-
García-Moreno, M.I.1
Benito, J.M.2
Ortiz Mellet, C.3
García Fernández, J.M.4
-
24
-
-
0242452497
-
-
(b) Díaz Pérez, V. M.; García-Moreno, M. I.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. J. Org. Chem. 2000, 65, 136.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 136
-
-
Díaz Pérez, V.M.1
García-Moreno, M.I.2
Ortiz Mellet, C.3
Fuentes, J.4
García Fernández, J.M.5
Díaz Arribas, J.C.6
Cañada, F.J.7
-
25
-
-
0030785113
-
-
(c) Jiménez Blanco, J. L.; Diaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969.
-
(1997)
Chem. Commun.
, pp. 1969
-
-
Jiménez Blanco, J.L.1
Diaz Pérez, V.M.2
Ortiz Mellet, C.3
Fuentes, J.4
García Fernández, J.M.5
Díaz Arribas, J.C.6
Cañada, F.J.7
-
26
-
-
0033097654
-
-
For reviews on trehazolin and close analogues ("trehazoloids"), see: (a) Berecibar, A.; Grandjean C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
-
(1999)
Chem. Rev.
, vol.99
, pp. 779
-
-
Berecibar, A.1
Grandjean, C.2
Siriwardena, A.3
-
28
-
-
0036903709
-
-
For recent reports on combinatorial synthetic strategies applied to the identification of selctive glycosidase inhibitors in the pyrrolidine azasugar series, see: (a) Gerber-Lemaire, S.; Popowycz, F.; Rodríguez-Garcí a, E.; Carmona Asenjo, A. T.; Robina, I.; Vogel, P. ChemBioChem 2002, 3, 466.
-
(2002)
ChemBioChem
, vol.3
, pp. 466
-
-
Gerber-Lemaire, S.1
Popowycz, F.2
Rodríguez-García, E.3
Carmona Asenjo, A.T.4
Robina, I.5
Vogel, P.6
-
29
-
-
0035194309
-
-
(b) Saotome, C.; Wong, C.-H.; Kanie, O. Chem. Biol. 2001, 8, 1061-1070.
-
(2001)
Chem. Biol.
, vol.8
, pp. 1061-1070
-
-
Saotome, C.1
Wong, C.-H.2
Kanie, O.3
-
30
-
-
0033036223
-
-
(c) Takebayashi, M.; Hiranuma, S.; Kanie, Y.; Kajimoto, T.; Kanie, O.; Wong, C.-H. J. Org. Chem. 1999, 64, 5280.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5280
-
-
Takebayashi, M.1
Hiranuma, S.2
Kanie, Y.3
Kajimoto, T.4
Kanie, O.5
Wong, C.-H.6
-
31
-
-
0035913152
-
-
Tatibouët, A.; Lefoix, M.; Nadolny, J.; Martin, O. R.; Rollin, P.; Yang, J.; Holman, G. D. Carbohydr. Res. 2001, 333, 327.
-
(2001)
Carbohydr. Res.
, vol.333
, pp. 327
-
-
Tatibouët, A.1
Lefoix, M.2
Nadolny, J.3
Martin, O.R.4
Rollin, P.5
Yang, J.6
Holman, G.D.7
-
32
-
-
37049125206
-
-
5-Azido-5-deoxy-D-fructopyranose derivatives have also been obtained from L-sorbose, an alternative starting material for DMDP synthesis; see: (a) Murphy, D. J. Chem. Soc. C 1967, 1732.
-
(1967)
J. Chem. Soc. C
, pp. 1732
-
-
Murphy, D.1
-
34
-
-
0037572030
-
-
For alternative recent syntheses of DMDP, see: (a) Donohoe, T. J.; Headley, C. E.; Cousins, R. P. C.; Cowley, A. Org. Lett. 2003, 5, 999.
-
(2003)
Org. Lett.
, vol.5
, pp. 999
-
-
Donohoe, T.J.1
Headley, C.E.2
Cousins, R.P.C.3
Cowley, A.4
-
35
-
-
2442517042
-
-
(b) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7003.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 7003
-
-
Dondoni, A.1
Giovannini, P.P.2
Perrone, D.3
-
36
-
-
0036676067
-
-
(c) Izquierdo, I.; Plaza, M. T.; Franco, F. Tetrahedron: Asymmetry 2002, 13, 1503.
-
(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 1503
-
-
Izquierdo, I.1
Plaza, M.T.2
Franco, F.3
-
37
-
-
0344712476
-
-
(d) Le merrer, Y.; Poitout, L.; Depezay, J.-C.; Dosbaa, I.; Geoffroy, S. ; Foglietti, M.-J. Bioorg. Med. Chem. 1997, 5, 519.
-
(1997)
Bioorg. Med. Chem.
, vol.5
, pp. 519
-
-
Le Merrer, Y.1
Poitout, L.2
Depezay, J.-C.3
Dosbaa, I.4
Geoffroy, S.5
Foglietti, M.-J.6
-
38
-
-
18544405939
-
-
(a) García-Moreno, M. I.; Díaz Pérez, P.; Ortiz Mellet, C.; García, Fernández, J. M. J. Org. Chem. 2003, 68, 8890.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 8890
-
-
García-Moreno, M.I.1
Díaz Pérez, P.2
Ortiz Mellet, C.3
García4
Fernández, J.M.5
-
39
-
-
0037149980
-
-
(b) García-Moreno, M. I.; Díaz Pérez, P.; Ortiz Mellet, C.; García Fernández, J. M. Chem. Commun. 2002, 848.
-
(2002)
Chem. Commun.
, pp. 848
-
-
García-Moreno, M.I.1
Díaz Pérez, P.2
Ortiz Mellet, C.3
García Fernández, J.M.4
-
40
-
-
85140868678
-
-
Camarasa, M. J.; Fernández-Resa, P.; Garcia-López, M. T.; de las Heras, F. G.; Méndez-Castrillón, P. P.; San Félix, A. Synthesis 1984, 509.
-
(1984)
Synthesis
, pp. 509
-
-
Camarasa, M.J.1
Fernández-Resa, P.2
Garcia-López, M.T.3
De Las Heras, F.G.4
Méndez-Castrillón, P.P.5
San Félix, A.6
-
42
-
-
0003532642
-
Tables of Glycosidase Inhibitors with Nitrogen in the Sugar Ring and Their Inhibitory Activities
-
Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany
-
Ekhart, C. W.; Fechter, M. H.; Hadwiger, P.; Mlaker, E.; Stütz, A. E.; Tauss, A., Wrodnigg, T. M. Tables of Glycosidase Inhibitors with Nitrogen in the Sugar Ring and Their Inhibitory Activities. In Iminosugars as Glycosidase Inhibitors; Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 253.
-
(1999)
Iminosugars as Glycosidase Inhibitors
, pp. 253
-
-
Ekhart, C.W.1
Fechter, M.H.2
Hadwiger, P.3
Mlaker, E.4
Stütz, A.E.5
Tauss, A.6
Wrodnigg, T.M.7
-
43
-
-
0002457082
-
Glycosidase Inhibition by Basic Sugar Analogues and the Transition State of Enzymatic Glycoside Hydrolysis
-
Stütz, A., Ed.; Wiley-VCH: Weinheim
-
Theoretical and experimental studies indicate that true transition state analogues must be essentially neutral or zwitterionic at physiological pH to keep specificity against the target enzyme. See: (a) Legler, G. Glycosidase Inhibition by Basic Sugar Analogues and the Transition State of Enzymatic Glycoside Hydrolysis. In Iminosugars as Glycosidase Inhibitors; Stütz, A., Ed.; Wiley-VCH: Weinheim, 1999; p 31
-
(1999)
Iminosugars as Glycosidase Inhibitors
, pp. 31
-
-
Legler, G.1
-
44
-
-
0029992305
-
-
(b) Jeong, J.-H.; Murray, B. W.; Takayama, S.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 4227.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 4227
-
-
Jeong, J.-H.1
Murray, B.W.2
Takayama, S.3
Wong, C.-H.4
-
46
-
-
0030496714
-
-
(d) Blériot, Y.; Genre-Grandpierre, A.; Imberty, A.; Tellier, C. J. Carbohydr. Chem. 1996, 15, 985.
-
(1996)
J. Carbohydr. Chem.
, vol.15
, pp. 985
-
-
Blériot, Y.1
Genre-Grandpierre, A.2
Imberty, A.3
Tellier, C.4
-
47
-
-
0029984524
-
-
(e) Deng, H.; Chan, A. W.-Y.; Bagdasianan, C. K.; Estupiñán, B.; Ganem, B.; Callender, R. H.; Scharamm, V. L. Biochemistry 1996, 35, 6037.
-
(1996)
Biochemistry
, vol.35
, pp. 6037
-
-
Deng, H.1
Chan, A.W.-Y.2
Bagdasianan, C.K.3
Estupiñán, B.4
Ganem, B.5
Callender, R.H.6
Scharamm, V.L.7
-
48
-
-
0027772603
-
-
(f) Ernert, P.; Vasella, A.; Weber, M.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113.
-
(1993)
Carbohydr. Res.
, vol.250
, pp. 113
-
-
Ernert, P.1
Vasella, A.2
Weber, M.3
Rupitz, K.4
Withers, S.G.5
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