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Volumn 61, Issue 12, 1996, Pages 4168-4171

Aminoacylation of nucleosides with FMOC amino acid fluorides

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE;

EID: 0029938956     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9601674     Document Type: Article
Times cited : (12)

References (26)
  • 10
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    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1989) Biochemistry , vol.28 , pp. 5185
    • Roesser, J.R.1    Xu, C.2    Payne, R.C.3    Surratt, C.K.4    Hecht, S.M.5
  • 11
    • 0024822218 scopus 로고
    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1989) Nucleic Acids Res. , vol.17 , pp. 9649
    • Robertson, S.A.1    Noren, C.J.2    Cahill, S.J.A.3    Griffith, M.C.4    Schultz, P.G.5
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    • 0023722101 scopus 로고
    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1988) Biochemistry , vol.27 , pp. 7951-7959
    • Baldini, G.1    Martoglio, B.2    Schachenmann, A.3    Zugliani, C.4    Brunner, J.5
  • 13
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    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 43-48
    • Herranz, R.1    Pichel, J.C.2    Lopez, M.T.G.3    Perez, C.4    Balzarini, J.5    De Clerq, E.6
  • 14
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    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1982) J. Org. Chem. , vol.47 , pp. 634
    • Kumar, G.1    Celewicz, L.2    Chládek, S.3
  • 15
    • 0023633862 scopus 로고
    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1987) J. Org. Chem. , vol.52 , pp. 5387
    • Happ, E.1    Scalfi-Happ, C.2    Chládek, S.3
  • 16
    • 0023814956 scopus 로고
    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1988) J. Org. Chem. , vol.53 , pp. 5040
    • Hagen, M.D.1    Scalfi-Happ, C.2    Happ, E.3    Chládek, S.4
  • 17
    • 0000237753 scopus 로고
    • Including 1,1′-carbonyldiimidazole: (a) Roesser, J. R.; Xu, C.; Payne, R. C.; Surratt, C. K.; Hecht, S. M. Biochemistry 1989, 28, 5185. (b) Robertson, S. A.; Noren, C. J.; Cahill, S. J. A.; Griffith, M. C.; Schultz, P. G. Nucleic Acids Res. 1989, 17, 9649. (c) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951-7959. BOP-Cl (N, JV-bis(2-oxooxazolidin-3-yl)-phosphorodiamidic chloride): Herranz, R.; Pichel, J. C.; Lopez, M. T. G.; Perez, C.; Balzarini, J.; De Clerq, E. J. Chem. Soc., Perkin Trans. 1 1991, 43-48. BPOC/MST ([[2-(4-biphenylyl)isopropyl]oxy]carbonyl/ (mesitylenesulfonyl)tetrazole): (a) Kumar, G.; Celewicz, L.; Chládek, S. J. Org. Chem. 1982, 47, 634. (b) Happ, E.; Scalfi-Happ, C.; Chládek, S. J. Org. Chem. 1987, 52, 5387. (c) Hagen, M. D.; Scalfi-Happ, C.; Happ, E.; Chládek, S. J. Org. Chem., 1988, 53, 5040. BOP/HOBT ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole): Bain, J. D.; Wacker, D. A.; Kuo, E. E.; Lyttle, M. H.; Chamberlin, A. R. J. Org. Chem. 1991, 56, 4615.
    • (1991) J. Org. Chem. , vol.56 , pp. 4615
    • Bain, J.D.1    Wacker, D.A.2    Kuo, E.E.3    Lyttle, M.H.4    Chamberlin, A.R.5


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