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(b) Dwek, R. A. Chem. Rev. 1996, 3, 683-720.
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6
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(a) Grogan, M. J.; Pratt, M. R.; Marcaurelle, L. A.; Bertozzi, C. R. Annu. Rev. Biochem. 2002, 71, 593-634.
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9
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0025074795
-
-
For other examples to construct the carbohydrate N-linkage see: (a) Günther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050-1051. (b) Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796-3797. (c) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409. (d) Maunier, V.; Boullanger, P.; Lafont, D. J. Carbohydr. Chem. 1997, 16, 231-235. (e) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165. (f) He, Y.; Hinklin, R. J.; Chang, J. Y.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
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Günther, W.1
Kunz, H.2
-
10
-
-
0000801006
-
-
For other examples to construct the carbohydrate N-linkage see: (a) Günther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050-1051. (b) Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796-3797. (c) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409. (d) Maunier, V.; Boullanger, P.; Lafont, D. J. Carbohydr. Chem. 1997, 16, 231-235. (e) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165. (f) He, Y.; Hinklin, R. J.; Chang, J. Y.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
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Handlon, A.L.1
Fraser-Reid, B.2
-
11
-
-
0037448919
-
-
For other examples to construct the carbohydrate N-linkage see: (a) Günther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050-1051. (b) Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796-3797. (c) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409. (d) Maunier, V.; Boullanger, P.; Lafont, D. J. Carbohydr. Chem. 1997, 16, 231-235. (e) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165. (f) He, Y.; Hinklin, R. J.; Chang, J. Y.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
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J. Am. Chem. Soc.
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Damkaci, F.1
DeShong, P.2
-
12
-
-
0031527883
-
-
For other examples to construct the carbohydrate N-linkage see: (a) Günther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050-1051. (b) Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796-3797. (c) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409. (d) Maunier, V.; Boullanger, P.; Lafont, D. J. Carbohydr. Chem. 1997, 16, 231-235. (e) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165. (f) He, Y.; Hinklin, R. J.; Chang, J. Y.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
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Maunier, V.1
Boullanger, P.2
Lafont, D.3
-
13
-
-
0032960774
-
-
For other examples to construct the carbohydrate N-linkage see: (a) Günther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050-1051. (b) Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796-3797. (c) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409. (d) Maunier, V.; Boullanger, P.; Lafont, D. J. Carbohydr. Chem. 1997, 16, 231-235. (e) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165. (f) He, Y.; Hinklin, R. J.; Chang, J. Y.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
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(1999)
Synthesis
, pp. 162-165
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Mizuno, M.1
Muramoto, I.2
Kobayashi, K.3
Yaginuma, H.4
Inazu, T.5
-
14
-
-
10044248464
-
-
For other examples to construct the carbohydrate N-linkage see: (a) Günther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050-1051. (b) Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796-3797. (c) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409. (d) Maunier, V.; Boullanger, P.; Lafont, D. J. Carbohydr. Chem. 1997, 16, 231-235. (e) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165. (f) He, Y.; Hinklin, R. J.; Chang, J. Y.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
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He, Y.1
Hinklin, R.J.2
Chang, J.Y.3
Kiessling, L.L.4
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15
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0041184214
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Likhoshertov, L. M.; Novikova, V. A.; Dervitskaja, V. A.; Kochetkov, N. K. Carbohydr. Res. 1986, 46, C1-C5.
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Kochetkov, N.K.4
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0025708612
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Takeda, T.; Utsuno, A.; Okamoto, N.; Ogihara, Y.; Shibata, S. Carbohydr. Res. 1980, 207, 71-79.
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84956430779
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18
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0035829084
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For a previous example of the synthesis of building block 2 see: Bosques, C. J.; Tai, V. W. F.; Imperiali, B. Tetrahedron Lett. 2001, 42, 7207-7210.
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Michael, F.; Frier, R.; Plate, E.; Hiller, A. Chem. Ber. 1952, 85, 1092-1096.
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0037468055
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(a) Miller, J. S.; Dudkin, V. Y.; Lyon, G. J.; Muir, T. W.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 431-434.
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(b) Wang, Z.-G.; Zhang, X.; Live, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 3652-3656.
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0036261973
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(a) Likhosherstov, L. M.; Novikova, O. S.; Shibaev, V. N. Dokl. Chem. 2002, 383, 89-92.
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0038703569
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4043179123
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Shibaev, V.N.4
-
30
-
-
17744395270
-
-
note
-
1H NMR spectroscopy and HPLC of fluorescently labeled substrates (see the Supporting Information for details).
-
-
-
-
31
-
-
0034595341
-
-
For examples of SPPS of glycopeptides using the building block approach see: (a) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. (b) Christiansen-Brams, I.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1993, 1461-1471. (c) Meinjohanns, E.; Meldal, M.; Paulsen, H.; Dwek, R. A.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1998, 549-560. (d) Holm, B.; Linse, S.; Kihlberg, J. Tetrahedron 1998, 54, 11995-12006. (e) Broddefalk, J.; Bergquist, K.; Kihlberg, J. Tetrahedron 1998, 54, 12047-12070.
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(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 1621-1624
-
-
Jobron, L.1
Hummel, G.2
-
32
-
-
37049073263
-
-
For examples of SPPS of glycopeptides using the building block approach see: (a) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. (b) Christiansen-Brams, I.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1993, 1461-1471. (c) Meinjohanns, E.; Meldal, M.; Paulsen, H.; Dwek, R. A.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1998, 549-560. (d) Holm, B.; Linse, S.; Kihlberg, J. Tetrahedron 1998, 54, 11995-12006. (e) Broddefalk, J.; Bergquist, K.; Kihlberg, J. Tetrahedron 1998, 54, 12047-12070.
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(1993)
J. Chem. Soc., Perkin Trans. 1
, pp. 1461-1471
-
-
Christiansen-Brams, I.1
Meldal, M.2
Bock, K.3
-
33
-
-
33748652962
-
-
For examples of SPPS of glycopeptides using the building block approach see: (a) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. (b) Christiansen-Brams, I.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1993, 1461-1471. (c) Meinjohanns, E.; Meldal, M.; Paulsen, H.; Dwek, R. A.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1998, 549-560. (d) Holm, B.; Linse, S.; Kihlberg, J. Tetrahedron 1998, 54, 11995-12006. (e) Broddefalk, J.; Bergquist, K.; Kihlberg, J. Tetrahedron 1998, 54, 12047-12070.
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(1998)
J. Chem. Soc., Perkin Trans. 1
, pp. 549-560
-
-
Meinjohanns, E.1
Meldal, M.2
Paulsen, H.3
Dwek, R.A.4
Bock, K.5
-
34
-
-
0032564016
-
-
For examples of SPPS of glycopeptides using the building block approach see: (a) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. (b) Christiansen-Brams, I.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1993, 1461-1471. (c) Meinjohanns, E.; Meldal, M.; Paulsen, H.; Dwek, R. A.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1998, 549-560. (d) Holm, B.; Linse, S.; Kihlberg, J. Tetrahedron 1998, 54, 11995-12006. (e) Broddefalk, J.; Bergquist, K.; Kihlberg, J. Tetrahedron 1998, 54, 12047-12070.
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(1998)
Tetrahedron
, vol.54
, pp. 11995-12006
-
-
Holm, B.1
Linse, S.2
Kihlberg, J.3
-
35
-
-
0032563988
-
-
For examples of SPPS of glycopeptides using the building block approach see: (a) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. (b) Christiansen-Brams, I.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1993, 1461-1471. (c) Meinjohanns, E.; Meldal, M.; Paulsen, H.; Dwek, R. A.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1998, 549-560. (d) Holm, B.; Linse, S.; Kihlberg, J. Tetrahedron 1998, 54, 11995-12006. (e) Broddefalk, J.; Bergquist, K.; Kihlberg, J. Tetrahedron 1998, 54, 12047-12070.
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(1998)
Tetrahedron
, vol.54
, pp. 12047-12070
-
-
Broddefalk, J.1
Bergquist, K.2
Kihlberg, J.3
-
36
-
-
0035793406
-
-
(a) Root, M. J.; Kay, M. S.; Kim, P. S. Science 2001, 291, 884-888.
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(2001)
Science
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-
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Root, M.J.1
Kay, M.S.2
Kim, P.S.3
-
38
-
-
0035897221
-
-
For the SPPS of a glycopeptide-thioester with a 26 amino acid sequence see: (a) Hojo, H.; Watabe, J.; Nakahara, Y.; Ito, Y.; Nabeshima, K.; Toole, B. P. Tetrahedron Lett. 2001, 42, 3001-3004. (b) Hojo, H.; Haginoya, E.; Matsumoto, Y.; Nakahara, Y.; Nabeshima, K.; Toole, B. P.; Watanabe, Y. Tetrahedron Lett. 2003, 44, 2961-2964.
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(2001)
Tetrahedron Lett.
, vol.42
, pp. 3001-3004
-
-
Hojo, H.1
Watabe, J.2
Nakahara, Y.3
Ito, Y.4
Nabeshima, K.5
Toole, B.P.6
-
39
-
-
0037474648
-
-
For the SPPS of a glycopeptide-thioester with a 26 amino acid sequence see: (a) Hojo, H.; Watabe, J.; Nakahara, Y.; Ito, Y.; Nabeshima, K.; Toole, B. P. Tetrahedron Lett. 2001, 42, 3001-3004. (b) Hojo, H.; Haginoya, E.; Matsumoto, Y.; Nakahara, Y.; Nabeshima, K.; Toole, B. P.; Watanabe, Y. Tetrahedron Lett. 2003, 44, 2961-2964.
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(2003)
Tetrahedron Lett.
, vol.44
, pp. 2961-2964
-
-
Hojo, H.1
Haginoya, E.2
Matsumoto, Y.3
Nakahara, Y.4
Nabeshima, K.5
Toole, B.P.6
Watanabe, Y.7
-
40
-
-
17744372663
-
-
note
-
We acknowledge Professor Michael J. Root for the SPPS of the peptide Y15-G39.
-
-
-
-
41
-
-
0025103048
-
-
(a) King, D. S.; Fields, C. G.; Fields, G. B. Int. J. Peptide Protein Res. 1990, 36, 255-266.
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King, D.S.1
Fields, C.G.2
Fields, G.B.3
|