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27
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12944273762
-
-
note
-
Typically no higher than ∼70% and up to 10 days. See ref 9.
-
-
-
-
28
-
-
0035194309
-
-
27 member
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Albeit modest in comparison to other compound libraries, this is a promising step for azasugars. For leading examples, see: (a) Saotome, C.; Wong, C.-H.; Kanie, O. Chem. Biol. 2001, 8, 1061 (27 member). (b) Wu, C.-Y.; Chang, C.-F.; Chen, J. S.-Y.; Wong, C.-H.; Lin, C.-H. Angew. Chem., Int. Ed. 2003, 42, 4661 (60 members). (c) Gerber-Lemaire, S.; Popowycz, F.; Rodríguez- García, E.; Asenjo, A. T. C.; Robina, I.; Vogel, P. ChemBioChem. 2002, 5, 466 (96 member).
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Saotome, C.1
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Kanie, O.3
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29
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-
0142119368
-
-
60 members
-
Albeit modest in comparison to other compound libraries, this is a promising step for azasugars. For leading examples, see: (a) Saotome, C.; Wong, C.-H.; Kanie, O. Chem. Biol. 2001, 8, 1061 (27 member). (b) Wu, C.-Y.; Chang, C.-F.; Chen, J. S.-Y.; Wong, C.-H.; Lin, C.-H. Angew. Chem., Int. Ed. 2003, 42, 4661 (60 members). (c) Gerber-Lemaire, S.; Popowycz, F.; Rodríguez- García, E.; Asenjo, A. T. C.; Robina, I.; Vogel, P. ChemBioChem. 2002, 5, 466 (96 member).
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Wu, C.-Y.1
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Lin, C.-H.5
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30
-
-
0036903709
-
-
96 member
-
Albeit modest in comparison to other compound libraries, this is a promising step for azasugars. For leading examples, see: (a) Saotome, C.; Wong, C.-H.; Kanie, O. Chem. Biol. 2001, 8, 1061 (27 member). (b) Wu, C.-Y.; Chang, C.-F.; Chen, J. S.-Y.; Wong, C.-H.; Lin, C.-H. Angew. Chem., Int. Ed. 2003, 42, 4661 (60 members). (c) Gerber-Lemaire, S.; Popowycz, F.; Rodríguez- García, E.; Asenjo, A. T. C.; Robina, I.; Vogel, P. ChemBioChem. 2002, 5, 466 (96 member).
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31
-
-
12944251195
-
-
note
-
Interestingly, little selectivity (dr 1:1) was seen for threitol 7vD.
-
-
-
-
32
-
-
0034002146
-
-
(a) Butters, T. D.; van den Broek, L. A. G. M.; Fleet, G. W. J.; Krulle T. M.; Wormald, M. R.; Dwek, R. A.; Platt, F. M. Tetrahedron: Asymmetry 2000, 11, 113.
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33
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(b) Fernandez, J. H.; Hayashi, M. A. F.; Camrgo, A. C. M.; Neshich, G. Biochem. Biophys. Res. Commun. 2003, 308, 219.
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34
-
-
12944293320
-
-
See Supporting Information for further details
-
See Supporting Information for further details.
-
-
-
-
35
-
-
12944291748
-
-
note
-
The reaction with benzyl isocyanide gave an anomalous yield of 49%.
-
-
-
-
36
-
-
12944330171
-
-
note
-
N-Methylpyrrole-2-carboxylic acid gave no Ugi product.
-
-
-
-
37
-
-
12944269223
-
-
note
-
No efficiency difference for either of the two enantiomers of imine 3.
-
-
-
-
40
-
-
0037180511
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41
-
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0028171083
-
-
and glycosidases (refs 3 and 8)
-
This was unexpected since imino sugars with hydrophobic substituents are inhibitors of GCS (see: Platt, F. M.; Neises, G. R.; Karlsson, G. B.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1994, 269, 27108) and glycosidases (refs 3 and 8).
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42
-
-
12944330172
-
-
note
-
Reduction with L-selectride or 9-BBN both proceeded sluggishly, even at reflux, and no trace of the reduction product could be detected.
-
-
-
-
44
-
-
12944275844
-
-
note
-
Although selectivities for 10 vs 11 were poor, pleasingly and strikingly, no reduction of the secondary amide was detected.
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45
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Factor inhibiting hypoxia-inducible factor, which catalyzes hydroxylation of VNAP motifs. See: (a) Hewitson, K. S.; McNeill, L. A.; Riordan, M. V.; Tian, Y. M.; Bullock, A. N.; Welford, R. W.; Elkins, J. M.; Oldham, N. J.; Battacharya, S.; Gleadle, J. M.; Ratcliffe, P. J.; Pugh, C. W.; Schofield, C. J. J. Biol. Chem. 2002, 277, 26351. (b) Lando, D.; Peel, D. J.; Whelan, D.; Gorman, J.; Whitelaw, M. Science 2002, 295, 858.
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Isoform of the prolyl hydroxylase domain containing hydroxylases. See: (a) Jaakkola, P.; Mole, D. R.; Tian, Y.-M.; Wilson, M. I.; Gielbert, J.; Gaskell, S. J.; von Kriegsheim, A.; Hebestreit, H. F.; Mukherji, M.; Schofield, C. J.; Maxwell, P. H.; Pugh, C. W.; Ratcliffe, P. J. Science 2001, 292, 468. (b) Ivan, M.; Kondo, K.; Yang, H.; Kim, W.; Valiando, J.; Ohh, M.; Salic, A.; Asara, J. M.; Lane, W. S.; Kaelin, W. G., Jr. Science 2001, 292, 464. (c) Epstein, A. C. R.; Gleadle, J. M.; McNeill, L. A.; Hewitson, K. S.; O'Rourke, J.; Mole, D. R.; Mukherji, M.; Metzen, E.; Wilson, M. I.; Dhanda, A.; Tian, Y.-M.; Masson, N.; Hamilton, D. L.; Jaakola, P.; Barstead, R.; Hodgkin, J.; Maxwell, P. H.; Pugh, C. W.; Schofield, C. J.; Ratcliffe, P. J. Cell 2001, 107, 43. (d) Schofield, C. J.; Ratcliffe, P. J. Nat. Rev. Mol. Cell. Biol. 2004, 5, 343.
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Isoform of the prolyl hydroxylase domain containing hydroxylases. See: (a) Jaakkola, P.; Mole, D. R.; Tian, Y.-M.; Wilson, M. I.; Gielbert, J.; Gaskell, S. J.; von Kriegsheim, A.; Hebestreit, H. F.; Mukherji, M.; Schofield, C. J.; Maxwell, P. H.; Pugh, C. W.; Ratcliffe, P. J. Science 2001, 292, 468. (b) Ivan, M.; Kondo, K.; Yang, H.; Kim, W.; Valiando, J.; Ohh, M.; Salic, A.; Asara, J. M.; Lane, W. S.; Kaelin, W. G., Jr. Science 2001, 292, 464. (c) Epstein, A. C. R.; Gleadle, J. M.; McNeill, L. A.; Hewitson, K. S.; O'Rourke, J.; Mole, D. R.; Mukherji, M.; Metzen, E.; Wilson, M. I.; Dhanda, A.; Tian, Y.-M.; Masson, N.; Hamilton, D. L.; Jaakola, P.; Barstead, R.; Hodgkin, J.; Maxwell, P. H.; Pugh, C. W.; Schofield, C. J.; Ratcliffe, P. J. Cell 2001, 107, 43. (d) Schofield, C. J.; Ratcliffe, P. J. Nat. Rev. Mol. Cell. Biol. 2004, 5, 343.
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