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Volumn 70, Issue 9, 2005, Pages 3574-3578

Improving glycopeptide synthesis: A convenient protocol for the preparation of β-glycosylamines and the synthesis of glycopeptides

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CARBOHYDRATES; METHANOL; PROTEINS; SOLUBILITY;

EID: 17744363690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047801v     Document Type: Article
Times cited : (36)

References (42)
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    • 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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    • 0037448919 scopus 로고    scopus 로고
    • 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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    • 0031527883 scopus 로고    scopus 로고
    • 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.
    • (1997) J. Carbohydr. Chem. , vol.16 , pp. 231-235
    • Maunier, V.1    Boullanger, P.2    Lafont, D.3
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    • 0032960774 scopus 로고    scopus 로고
    • 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.
    • (1999) Synthesis , pp. 162-165
    • Mizuno, M.1    Muramoto, I.2    Kobayashi, K.3    Yaginuma, H.4    Inazu, T.5
  • 14
    • 10044248464 scopus 로고    scopus 로고
    • 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.
    • (2004) Org. Lett. , vol.6 , pp. 4479-4482
    • He, Y.1    Hinklin, R.J.2    Chang, J.Y.3    Kiessling, L.L.4
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    • note
    • 1H NMR spectroscopy and HPLC of fluorescently labeled substrates (see the Supporting Information for details).
  • 31
    • 0034595341 scopus 로고    scopus 로고
    • 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.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1621-1624
    • Jobron, L.1    Hummel, G.2
  • 32
    • 37049073263 scopus 로고
    • 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.
    • (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 1461-1471
    • Christiansen-Brams, I.1    Meldal, M.2    Bock, K.3
  • 33
    • 33748652962 scopus 로고    scopus 로고
    • 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.
    • (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 scopus 로고    scopus 로고
    • 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.
    • (1998) Tetrahedron , vol.54 , pp. 11995-12006
    • Holm, B.1    Linse, S.2    Kihlberg, J.3
  • 35
    • 0032563988 scopus 로고    scopus 로고
    • 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.
    • (1998) Tetrahedron , vol.54 , pp. 12047-12070
    • Broddefalk, J.1    Bergquist, K.2    Kihlberg, J.3
  • 37
  • 38
    • 0035897221 scopus 로고    scopus 로고
    • 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.
    • (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
  • 40
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    • note
    • We acknowledge Professor Michael J. Root for the SPPS of the peptide Y15-G39.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.