-
1
-
-
0031922295
-
-
See, for instance: Hinterding, K.; Alonso-Díaz, D.; Waldmann, H. Angew. Chem., Int. Ed. 1998, 37, 688-749.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 688-749
-
-
Hinterding, K.1
Alonso-Díaz, D.2
Waldmann, H.3
-
2
-
-
0034676587
-
-
Okeley, N. M.; Zhu, Y.; van der Donk, W. A. Org. Lett. 2000, 2, 3603-3606.
-
(2000)
Org. Lett.
, vol.2
, pp. 3603-3606
-
-
Okeley, N.M.1
Zhu, Y.2
Van Der Donk, W.A.3
-
3
-
-
13344291142
-
-
For selected examples and reviews of this approach in glycopeptide synthesis, see: (a) Andreotti, A. H.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 3352-3353.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 3352-3353
-
-
Andreotti, A.H.1
Kahne, D.2
-
4
-
-
0029093071
-
-
(b) Szabo, L.; Ramza, J.; Langdon, C.; Polt, R. Carbohydr. Res. 1995, 274, 11-28.
-
(1995)
Carbohydr. Res.
, vol.274
, pp. 11-28
-
-
Szabo, L.1
Ramza, J.2
Langdon, C.3
Polt, R.4
-
5
-
-
0028807564
-
-
(c) Meinjohanns, E.; Meldal, M.; Bock, K. Tetrahedron Lett. 1995, 50, 9205-9208.
-
(1995)
Tetrahedron Lett.
, vol.50
, pp. 9205-9208
-
-
Meinjohanns, E.1
Meldal, M.2
Bock, K.3
-
6
-
-
0003867841
-
-
Montreuil, J., Schacter, H., Vliegenthart, J. F. G., Eds.; Elsevier: Amsterdam
-
(d) Paulsen, H.; Peters. S.; Bielfeldt, T., In Glycoproteins; Montreuil, J., Schacter, H., Vliegenthart, J. F. G., Eds.; Elsevier: Amsterdam, 1995.
-
(1995)
Glycoproteins
-
-
Paulsen, H.1
Peters, S.2
Bielfeldt, T.3
-
7
-
-
0030773830
-
-
(e) Sames, D.; Chen, X. T.; Danishefsky, S. J. Nature 1997, 389, 587-591.
-
(1997)
Nature
, vol.389
, pp. 587-591
-
-
Sames, D.1
Chen, X.T.2
Danishefsky, S.J.3
-
8
-
-
0030933156
-
-
(f) Klich, G.; Paulsen, H.; Meyer, B.; Meldal, M.; Bock, K. Carbohydr. Res. 1997, 299, 33-48.
-
(1997)
Carbohydr. Res.
, vol.299
, pp. 33-48
-
-
Klich, G.1
Paulsen, H.2
Meyer, B.3
Meldal, M.4
Bock, K.5
-
10
-
-
0032501470
-
-
(h) Kuduk, S. D.; Schwarz, J. B.; Chen, X. T.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 12474-12485.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 12474-12485
-
-
Kuduk, S.D.1
Schwarz, J.B.2
Chen, X.T.3
Glunz, P.W.4
Sames, D.5
Ragupathi, G.6
Livingston, P.O.7
Danishefsky, S.J.8
-
11
-
-
0033533481
-
-
(i) Winans, K. A.; King, D. S.; Rao, V. R.; Bertozzi, C. R. Biochemistry 1999, 38, 11700-11710.
-
(1999)
Biochemistry
, vol.38
, pp. 11700-11710
-
-
Winans, K.A.1
King, D.S.2
Rao, V.R.3
Bertozzi, C.R.4
-
12
-
-
0033620366
-
-
(j) Schwarz, J. B.; Kuduk, S. D.; Chen, X. T.; Sames, D.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 2662-2673.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 2662-2673
-
-
Schwarz, J.B.1
Kuduk, S.D.2
Chen, X.T.3
Sames, D.4
Glunz, P.W.5
Danishefsky, S.J.6
-
13
-
-
0001108902
-
-
(k) Duus, J. O.; St Hilaire, P. M.; Meldal, M.; Bock, K. Pure Appl. Chem. 1999, 71, 755-765.
-
(1999)
Pure Appl. Chem.
, vol.71
, pp. 755-765
-
-
Duus, J.O.1
St Hilaire, P.M.2
Meldal, M.3
Bock, K.4
-
14
-
-
0034504913
-
-
(l) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem Rev. 2000, 100, 4495-4537.
-
(2000)
Chem Rev.
, vol.100
, pp. 4495-4537
-
-
Herzner, H.1
Reipen, T.2
Schultz, M.3
Kunz, H.4
-
15
-
-
0011217950
-
-
(a) St Hilaire. P. M.; Lowary, T. L.; Meldal, M.; Bock, K. J. Am. Chem. Soc. 1998, 120, 13312-13320.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 13312-13320
-
-
St Hilaire, P.M.1
Lowary, T.L.2
Meldal, M.3
Bock, K.4
-
16
-
-
0034149935
-
-
(b) Arya, P.; Kutterer, K. M. K.; Barkley, A. J. Comb. Chem. 2000, 2, 120-126.
-
(2000)
J. Comb. Chem.
, vol.2
, pp. 120-126
-
-
Arya, P.1
Kutterer, K.M.K.2
Barkley, A.3
-
17
-
-
0026826660
-
-
For other electrophilic handles that have been introduced into peptides, see: (a) Geoghegan, K. F.; Stroh, J. G. Bioconj. Chem. 1992, 3, 138-146.
-
(1992)
Bioconj. Chem.
, vol.3
, pp. 138-146
-
-
Geoghegan, K.F.1
Stroh, J.G.2
-
20
-
-
0034685521
-
-
(d) Bark, S. J.; Schmid, S.; Hahn, K. M. J. Am. Chem. Soc. 2000, 122, 3567-3573.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 3567-3573
-
-
Bark, S.J.1
Schmid, S.2
Hahn, K.M.3
-
21
-
-
0024465343
-
-
(a) Gutierrez, L.; Magee, A. I.; Marshall, C. J.; Hancock, J. F. EMBO J. 1989, 8, 1093-1098.
-
(1989)
EMBO J.
, vol.8
, pp. 1093-1098
-
-
Gutierrez, L.1
Magee, A.I.2
Marshall, C.J.3
Hancock, J.F.4
-
22
-
-
0025277259
-
-
(b) Glomset, J. A.; Gelb, M. H.; Famsworth, C. C. Trends Biochem. Sci. 1990, 15, 139-142.
-
(1990)
Trends Biochem. Sci.
, vol.15
, pp. 139-142
-
-
Glomset, J.A.1
Gelb, M.H.2
Famsworth, C.C.3
-
26
-
-
0025194466
-
-
(a) Reiss, Y.; Goldstein, J. L.; Seabra, M. C.; Casey, P. J.; Brown M. S. Cell 1990, 62, 81-88.
-
(1990)
Cell
, vol.62
, pp. 81-88
-
-
Reiss, Y.1
Goldstein, J.L.2
Seabra, M.C.3
Casey, P.J.4
Brown, M.S.5
-
30
-
-
0033605743
-
-
(d) Otto, J. C.; Kim, E.; Young, S. G.; Casey, P. J. J. Biol. Chem. 1999, 274, 8379-8382.
-
(1999)
J. Biol. Chem.
, vol.274
, pp. 8379-8382
-
-
Otto, J.C.1
Kim, E.2
Young, S.G.3
Casey, P.J.4
-
31
-
-
0025046234
-
-
(a) Fukada, Y.; Takao, T.; Ohguro, H.; Yoshizawa, T.; Akino, T.; Shimonishi, Y. Nature 1990, 346, 658-660.
-
(1990)
Nature
, vol.346
, pp. 658-660
-
-
Fukada, Y.1
Takao, T.2
Ohguro, H.3
Yoshizawa, T.4
Akino, T.5
Shimonishi, Y.6
-
33
-
-
0025203316
-
-
(c) Kawata, M.; Farnsworth, C. C.; Yoshida, Y.; Gelb, M. H.; Glomset, J. A.; Takai, Y. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 8960-8964.
-
(1990)
Proc. Natl. Acad. Sci. U.S.A.
, vol.87
, pp. 8960-8964
-
-
Kawata, M.1
Farnsworth, C.C.2
Yoshida, Y.3
Gelb, M.H.4
Glomset, J.A.5
Takai, Y.6
-
34
-
-
0025764049
-
-
(d) Hrycyna, C. A.; Sapperstein, S. K.; Clarke, S.; Michaelis, S. EMBO J. 1991, 10, 1699-1709.
-
(1991)
EMBO J.
, vol.10
, pp. 1699-1709
-
-
Hrycyna, C.A.1
Sapperstein, S.K.2
Clarke, S.3
Michaelis, S.4
-
35
-
-
0026346215
-
-
(e) Perez-Sala, D.; Tan, E. W.; Canada, F. J.; Rando, R. R. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 3043-3046.
-
(1991)
Proc. Natl. Acad. Sci. U.S.A.
, vol.88
, pp. 3043-3046
-
-
Perez-Sala, D.1
Tan, E.W.2
Canada, F.J.3
Rando, R.R.4
-
36
-
-
0024406286
-
-
Hancock, J. F.; Magee, A. I.; Childs, J. E.; Marshall, C. J. Cell 1989, 57, 1167-1177.
-
(1989)
Cell
, vol.57
, pp. 1167-1177
-
-
Hancock, J.F.1
Magee, A.I.2
Childs, J.E.3
Marshall, C.J.4
-
37
-
-
0026061739
-
-
Reiss, Y.; Stradley, S. J.; Gierasch, L. M.; Brown, M. S.; Goldstein, J. L. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 732-736.
-
(1991)
Proc. Natl. Acad. Sci. U.S.A.
, vol.88
, pp. 732-736
-
-
Reiss, Y.1
Stradley, S.J.2
Gierasch, L.M.3
Brown, M.S.4
Goldstein, J.L.5
-
38
-
-
0027527703
-
-
(a) Jang, G. F.; Yokoyama, K.; Gelb, M. H. Biochemistry 1993, 32, 9500-9507.
-
(1993)
Biochemistry
, vol.32
, pp. 9500-9507
-
-
Jang, G.F.1
Yokoyama, K.2
Gelb, M.H.3
-
39
-
-
0029041182
-
-
(b) Liu, L.; Jang, G. F.; Farnsworth, C. C.; Yokoyama, K.; Glomset, J. A.; Gelb, M. H. Methods Enzymol. 1995, 250, 189-206.
-
(1995)
Methods Enzymol.
, vol.250
, pp. 189-206
-
-
Liu, L.1
Jang, G.F.2
Farnsworth, C.C.3
Yokoyama, K.4
Glomset, J.A.5
Gelb, M.H.6
-
40
-
-
0028999660
-
-
Volker, C.; Pillinger, M. H.; Philips, M. R.; Stock, J. B. Methods Enzymol. 1995, 250, 216-225.
-
(1995)
Methods Enzymol.
, vol.250
, pp. 216-225
-
-
Volker, C.1
Pillinger, M.H.2
Philips, M.R.3
Stock, J.B.4
-
42
-
-
0029026643
-
-
(a) Gilbert, B. A.; Ma, Y. T.; Rando, R. R. Methods Enzymol. 1995, 250, 206-15.
-
(1995)
Methods Enzymol.
, vol.250
, pp. 206-215
-
-
Gilbert, B.A.1
Ma, Y.T.2
Rando, R.R.3
-
43
-
-
0029000603
-
-
(b) Ma, Y. T.; Gilbert, B. A.; Rando, R. R. Methods Enzymol. 1995, 250, 226-234.
-
(1995)
Methods Enzymol.
, vol.250
, pp. 226-234
-
-
Ma, Y.T.1
Gilbert, B.A.2
Rando, R.R.3
-
44
-
-
0028848171
-
-
McGeady, P.; Kuroda, S.; Shimizu, K.; Takai, Y.; Gelb, M. H. J. Biol. Chem. 1995, 270, 26347-26351.
-
(1995)
J. Biol. Chem.
, vol.270
, pp. 26347-26351
-
-
McGeady, P.1
Kuroda, S.2
Shimizu, K.3
Takai, Y.4
Gelb, M.H.5
-
45
-
-
25944478374
-
-
(a) Stöber, P.; Schelhaas, M.; Nägele, E.; Hagenbuch, P.; Rétey, J.; Waldmann, H. Bioorg. Med. Chem. Lett. 1997, 5, 775-83.
-
(1997)
Bioorg. Med. Chem. Lett.
, vol.5
, pp. 775-783
-
-
Stöber, P.1
Schelhaas, M.2
Nägele, E.3
Hagenbuch, P.4
Rétey, J.5
Waldmann, H.6
-
46
-
-
0032558108
-
-
(b) Nägele, E.; Schelhaas, M.; Kuder, N.; Waldmann, H. J. Am. Chem. Soc. 1998, 120, 6889-6902.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 6889-6902
-
-
Nägele, E.1
Schelhaas, M.2
Kuder, N.3
Waldmann, H.4
-
48
-
-
0030056960
-
-
(a) Schelhaas, M.; Glomsda, S.; Hansler, M.; Jakubke, H. D.; Waldmann, H. Angew. Chem. Int. Ed. Engl. 1996, 35, 106-109.
-
(1996)
Angew. Chem. Int. Ed. Engl.
, vol.35
, pp. 106-109
-
-
Schelhaas, M.1
Glomsda, S.2
Hansler, M.3
Jakubke, H.D.4
Waldmann, H.5
-
49
-
-
0030708812
-
-
(b) Waldmann, H.; Schelhaas, M.; Nagele, E.; Kuhlmann, J.; Wittinghofer, A.; Schroeder, H.; Silvius, J. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 2238-2241.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2238-2241
-
-
Waldmann, H.1
Schelhaas, M.2
Nagele, E.3
Kuhlmann, J.4
Wittinghofer, A.5
Schroeder, H.6
Silvius, J.R.7
-
50
-
-
0030696229
-
-
(c) Schroeder, H.; Leventis, R.; Rex, S.; Schelhaas, M.; Nagele, E.; Waldmann, H.; Silvius, J. R. Biochemistry 1997, 36, 13102-13109.
-
(1997)
Biochemistry
, vol.36
, pp. 13102-13109
-
-
Schroeder, H.1
Leventis, R.2
Rex, S.3
Schelhaas, M.4
Nagele, E.5
Waldmann, H.6
Silvius, J.R.7
-
51
-
-
0344197079
-
-
(d) Schelhaas, M.; Nagele, E.; Kuder, N.; Bader, B.; Kuhlmann, J.; Wittinghofer, A.; Waldmann, H. Chem. Eur. J. 1999, 5, 1239-1252.
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 1239-1252
-
-
Schelhaas, M.1
Nagele, E.2
Kuder, N.3
Bader, B.4
Kuhlmann, J.5
Wittinghofer, A.6
Waldmann, H.7
-
52
-
-
0034642495
-
-
(e) Bader, B.; Kuhn, K.; Owen, D. J.; Waldmann, H.; Wittinghofer, A.; Kuhlmann, J. Nature 2000, 403, 223-226.
-
(2000)
Nature
, vol.403
, pp. 223-226
-
-
Bader, B.1
Kuhn, K.2
Owen, D.J.3
Waldmann, H.4
Wittinghofer, A.5
Kuhlmann, J.6
-
53
-
-
0034619267
-
-
For another recent example of Michael additions to dehydroalanines, see: Ferreira, P. M. T.; Maia, H. L. S.; Sacramento, J.; Sebastião, J. J. Chem. Soc., Perkin Trans. 1 2000, 3317-3324.
-
(2000)
J. Chem. Soc., Perkin Trans. 1
, pp. 3317-3324
-
-
Ferreira, P.M.T.1
Maia, H.L.S.2
Sacramento, J.3
Sebastião, J.4
-
54
-
-
0016892854
-
-
Diastereoselective Michael addition (9:1) of methanethiol to proline-dehydroalanine dipeptides has been reported: Schmidt, U.; Öhler, E. Angew. Chem., Int. Ed. Engl. 1976, 15, 42.
-
(1976)
Angew. Chem., Int. Ed. Engl.
, vol.15
, pp. 42
-
-
Schmidt, U.1
Öhler, E.2
-
56
-
-
0028316394
-
-
(b) Gerz, M.; Matter, H.; Kessler, H. Int. J. Pept. Prot. Res. 1994, 43, 248-257.
-
(1994)
Int. J. Pept. Prot. Res.
, vol.43
, pp. 248-257
-
-
Gerz, M.1
Matter, H.2
Kessler, H.3
-
61
-
-
0034354953
-
-
(g) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541.
-
(2000)
Carbohydr. Chem.
, vol.19
, pp. 527-541
-
-
Bousquet, E.1
Spadaro, A.2
Pappalardo, M.S.3
Bernardini, R.4
Romeo, R.5
Panza, L.6
Ronsisvalle, G.J.7
-
62
-
-
0041363637
-
-
US 5,932,554, 1999; US 5,968,907, 1999
-
The patent literature contains reports of successful Michael additions of thioglycosides to Michael acceptors such as cyclopentenone and cyclohexenone: Hindsgaul, O. US 5,932,554, 1999; US 5,968,907, 1999.
-
-
-
Hindsgaul, O.1
-
64
-
-
0027227464
-
-
(a) Baribault, H.; Price, J.; Miyai, K.; Oshima, R. G. Genes Dev. 1993, 7, 1191-1202.
-
(1993)
Genes Dev.
, vol.7
, pp. 1191-1202
-
-
Baribault, H.1
Price, J.2
Miyai, K.3
Oshima, R.G.4
-
65
-
-
0028607055
-
-
(b) Baribault, H.; Penner, J.; Iozzo, R. V.; Wilson-Heiner, M. Genes Dev. 1994, 8, 2964-2973.
-
(1994)
Genes Dev.
, vol.8
, pp. 2964-2973
-
-
Baribault, H.1
Penner, J.2
Iozzo, R.V.3
Wilson-Heiner, M.4
-
66
-
-
0034596918
-
-
(c) Hesse, M.; Franz, T.; Tamai, Y.; Taketo, M. M.; Magin, T. M. EMBO J. 2000, 19, 5060-5070.
-
(2000)
EMBO J.
, vol.19
, pp. 5060-5070
-
-
Hesse, M.1
Franz, T.2
Tamai, Y.3
Taketo, M.M.4
Magin, T.M.5
-
67
-
-
0032403911
-
-
(a) Ishida-Yamamoto, A.; Tanaka, H.; Nakane, H.; Takahashi, H.; Iizuka, H. J. Dermatol. Sci. 1998, 18, 139-154.
-
(1998)
J. Dermatol. Sci.
, vol.18
, pp. 139-154
-
-
Ishida-Yamamoto, A.1
Tanaka, H.2
Nakane, H.3
Takahashi, H.4
Iizuka, H.5
-
69
-
-
0030473762
-
-
(c) Oshima, R. G.; Baribault, H.; Caulin, C. Cancer Metastasis Rev. 1996, 15, 445-471.
-
(1996)
Cancer Metastasis Rev.
, vol.15
, pp. 445-471
-
-
Oshima, R.G.1
Baribault, H.2
Caulin, C.3
-
72
-
-
0035825787
-
-
For a different example of using unprotected 1-thio sugars to link carbohydrates to amino acids, see: Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407.
-
(2001)
Org. Lett.
, vol.3
, pp. 405-407
-
-
Cohen, S.B.1
Halcomb, R.L.2
-
74
-
-
0027944205
-
-
(a) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. Science 1994, 266, 776-779.
-
(1994)
Science
, vol.266
, pp. 776-779
-
-
Dawson, P.E.1
Muir, T.W.2
Clark-Lewis, I.3
Kent, S.B.4
-
75
-
-
0032499752
-
-
(b) Muir, T. W.; Sondhi, D.; Cole, P. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 6705-6710.
-
(1998)
Proc. Natl. Acad. Sci. U.S.A.
, vol.95
, pp. 6705-6710
-
-
Muir, T.W.1
Sondhi, D.2
Cole, P.A.3
-
76
-
-
0344351815
-
-
(c) Evans, T. C.; Benner, J.; Xu, M. Q. Protein Sci. 1998, 7, 2256-2264.
-
(1998)
Protein Sci.
, vol.7
, pp. 2256-2264
-
-
Evans, T.C.1
Benner, J.2
Xu, M.Q.3
-
78
-
-
0034602984
-
-
(e) Noren, C. J.; Wang, J. M.; Perler, F. B. Angew. Chem., Int. Ed. 2000, 39, 451-466.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 451-466
-
-
Noren, C.J.1
Wang, J.M.2
Perler, F.B.3
|