Extremely mild reagent for Boc deprotection applicable to the synthesis of peptides with thioamide linkages

Chemical Communications

Volumn , Issue 22, 1996, Pages 2509-2510

  Frank, Robert ^a   Schutkowski, Mike ^a  

^a MAX PLANCK INSTITUTE OF MICROSTRUCTURE PHYSICS   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003075017     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960002509     Document Type: Article

References (29)

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2. P. Campbell and N. T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221; P. A. Bartlett, K. L. Spear and N. E. Jacobson, Biochemistry, 1982, 21, 1608; B. Asbóth and L. Polgar, Biochemistry, 1983, 22, 117; M. D. Bond, B. Holmquist and B. L. Vallee, J. Inorg. Biochem., 1986, 28, 97; L. Maziak, G. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, R. E. Beattie, D. T. Elmore, C. H. Williams and D. J. S. Guthrie, Biochem. J., 1987, 245, 285; L. Polgar, E. Kollat and M. Hollosi, FEBS Lett., 1993, 322, 227; M. Schutkowski, K. Neubert and G. Fischer, Eur. J. Biochem., 1994, 221, 455. R. Bardi, A. M. Piazzesi, C. Toniolo, O. E. Jensen, R. S. Omar and A. Senning, Biopolymers, 1988, 27, 747.
3. P. Campbell and N. T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221; P. A. Bartlett, K. L. Spear and N. E. Jacobson, Biochemistry, 1982, 21, 1608; B. Asbóth and L. Polgar, Biochemistry, 1983, 22, 117; M. D. Bond, B. Holmquist and B. L. Vallee, J. Inorg. Biochem., 1986, 28, 97; L. Maziak, G. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, R. E. Beattie, D. T. Elmore, C. H. Williams and D. J. S. Guthrie, Biochem. J., 1987, 245, 285; L. Polgar, E. Kollat and M. Hollosi, FEBS Lett., 1993, 322, 227; M. Schutkowski, K. Neubert and G. Fischer, Eur. J. Biochem., 1994, 221, 455. R. Bardi, A. M. Piazzesi, C. Toniolo, O. E. Jensen, R. S. Omar and A. Senning, Biopolymers, 1988, 27, 747.
4. P. Campbell and N. T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221; P. A. Bartlett, K. L. Spear and N. E. Jacobson, Biochemistry, 1982, 21, 1608; B. Asbóth and L. Polgar, Biochemistry, 1983, 22, 117; M. D. Bond, B. Holmquist and B. L. Vallee, J. Inorg. Biochem., 1986, 28, 97; L. Maziak, G. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, R. E. Beattie, D. T. Elmore, C. H. Williams and D. J. S. Guthrie, Biochem. J., 1987, 245, 285; L. Polgar, E. Kollat and M. Hollosi, FEBS Lett., 1993, 322, 227; M. Schutkowski, K. Neubert and G. Fischer, Eur. J. Biochem., 1994, 221, 455. R. Bardi, A. M. Piazzesi, C. Toniolo, O. E. Jensen, R. S. Omar and A. Senning, Biopolymers, 1988, 27, 747.
5. P. Campbell and N. T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221; P. A. Bartlett, K. L. Spear and N. E. Jacobson, Biochemistry, 1982, 21, 1608; B. Asbóth and L. Polgar, Biochemistry, 1983, 22, 117; M. D. Bond, B. Holmquist and B. L. Vallee, J. Inorg. Biochem., 1986, 28, 97; L. Maziak, G. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, R. E. Beattie, D. T. Elmore, C. H. Williams and D. J. S. Guthrie, Biochem. J., 1987, 245, 285; L. Polgar, E. Kollat and M. Hollosi, FEBS Lett., 1993, 322, 227; M. Schutkowski, K. Neubert and G. Fischer, Eur. J. Biochem., 1994, 221, 455. R. Bardi, A. M. Piazzesi, C. Toniolo, O. E. Jensen, R. S. Omar and A. Senning, Biopolymers, 1988, 27, 747.
6. P. Campbell and N. T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221; P. A. Bartlett, K. L. Spear and N. E. Jacobson, Biochemistry, 1982, 21, 1608; B. Asbóth and L. Polgar, Biochemistry, 1983, 22, 117; M. D. Bond, B. Holmquist and B. L. Vallee, J. Inorg. Biochem., 1986, 28, 97; L. Maziak, G. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, R. E. Beattie, D. T. Elmore, C. H. Williams and D. J. S. Guthrie, Biochem. J., 1987, 245, 285; L. Polgar, E. Kollat and M. Hollosi, FEBS Lett., 1993, 322, 227; M. Schutkowski, K. Neubert and G. Fischer, Eur. J. Biochem., 1994, 221, 455. R. Bardi, A. M. Piazzesi, C. Toniolo, O. E. Jensen, R. S. Omar and A. Senning, Biopolymers, 1988, 27, 747.
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8. P. Campbell and N. T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221; P. A. Bartlett, K. L. Spear and N. E. Jacobson, Biochemistry, 1982, 21, 1608; B. Asbóth and L. Polgar, Biochemistry, 1983, 22, 117; M. D. Bond, B. Holmquist and B. L. Vallee, J. Inorg. Biochem., 1986, 28, 97; L. Maziak, G. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, R. E. Beattie, D. T. Elmore, C. H. Williams and D. J. S. Guthrie, Biochem. J., 1987, 245, 285; L. Polgar, E. Kollat and M. Hollosi, FEBS Lett., 1993, 322, 227; M. Schutkowski, K. Neubert and G. Fischer, Eur. J. Biochem., 1994, 221, 455. R. Bardi, A. M. Piazzesi, C. Toniolo, O. E. Jensen, R. S. Omar and A. Senning, Biopolymers, 1988, 27, 747.
9. P. Campbell and N. T. Nashed, J. Am. Chem. Soc., 1982, 104, 5221; P. A. Bartlett, K. L. Spear and N. E. Jacobson, Biochemistry, 1982, 21, 1608; B. Asbóth and L. Polgar, Biochemistry, 1983, 22, 117; M. D. Bond, B. Holmquist and B. L. Vallee, J. Inorg. Biochem., 1986, 28, 97; L. Maziak, G. Lajoie and B. Belleau, J. Am. Chem. Soc., 1986, 108, R. E. Beattie, D. T. Elmore, C. H. Williams and D. J. S. Guthrie, Biochem. J., 1987, 245, 285; L. Polgar, E. Kollat and M. Hollosi, FEBS Lett., 1993, 322, 227; M. Schutkowski, K. Neubert and G. Fischer, Eur. J. Biochem., 1994, 221, 455. R. Bardi, A. M. Piazzesi, C. Toniolo, O. E. Jensen, R. S. Omar and A. Senning, Biopolymers, 1988, 27, 747.
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14. Preparation of thiazoles and N-heterocycles: J. Gasteiger and C. Herzig, Tetrahedron, 1981, 15, 2607; J. D. Coyle, Tetrahedron, 1985, 41, 5393 and references cited therein. Synthesis of β-lactams: M. Sakamoto, S. Watanabe, T. Fujita, M. Tohnishi, H. Aoyama and Y. Omote, J. Chem. Soc., Perkin Trans. 1, 1988, 2203. Reduction to desoxopeptide bonds: F. S. Guziec, Jr. and L. M. Wasmund, Tetrahedron Lett., 1990, 31, 23.
15. Preparation of thiazoles and N-heterocycles: J. Gasteiger and C. Herzig, Tetrahedron, 1981, 15, 2607; J. D. Coyle, Tetrahedron, 1985, 41, 5393 and references cited therein. Synthesis of β-lactams: M. Sakamoto, S. Watanabe, T. Fujita, M. Tohnishi, H. Aoyama and Y. Omote, J. Chem. Soc., Perkin Trans. 1, 1988, 2203. Reduction to desoxopeptide bonds: F. S. Guziec, Jr. and L. M. Wasmund, Tetrahedron Lett., 1990, 31, 23.
16. Preparation of thiazoles and N-heterocycles: J. Gasteiger and C. Herzig, Tetrahedron, 1981, 15, 2607; J. D. Coyle, Tetrahedron, 1985, 41, 5393 and references cited therein. Synthesis of β-lactams: M. Sakamoto, S. Watanabe, T. Fujita, M. Tohnishi, H. Aoyama and Y. Omote, J. Chem. Soc., Perkin Trans. 1, 1988, 2203. Reduction to desoxopeptide bonds: F. S. Guziec, Jr. and L. M. Wasmund, Tetrahedron Lett., 1990, 31, 23.
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