메뉴 건너뛰기




Volumn 121, Issue 40, 1999, Pages 9286-9298

Design and synthesis of a competent pyrrolinone-peptide hybrid ligand for the class II major histocompatibility complex protein HLA-DR1

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; HLA DR1 ANTIGEN; HYBRID PROTEIN; LIGAND; PYRROLE DERIVATIVE; VIRUS HEMAGGLUTININ;

EID: 0033552280     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991251e     Document Type: Article
Times cited : (44)

References (86)
  • 1
  • 3
    • 0000788606 scopus 로고
    • Weinstein, B. Ed.; Marcel Dekker: New York
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1983) Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins , vol.7 , pp. 267-357
    • Spatola, A.F.1
  • 4
    • 0027423502 scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1993) J. Med. Chem. , vol.36 , pp. 3039
    • Olson, G.L.1    Bolin, D.R.2    Bonner, M.P.3    Bos, M.4    Cook, C.M.5    Fry, D.C.6    Graves, B.J.7    Hatada, M.8    Hill, D.E.9    Kahn, M.10    Madison, V.S.11    Rusiecki, V.K.12    Sarabu, R.13    Sepinwall, J.14    Vincent, G.P.15    Voss, M.E.16
  • 5
    • 0027478912 scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1993) Med. Res. Rev. , vol.13 , pp. 327
    • Wiley, R.A.1    Rich, D.H.2
  • 6
    • 0028038601 scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1699
    • Gante, J.1
  • 7
    • 0030884435 scopus 로고    scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell-Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1997) Biopolymers , vol.43 , pp. 219
    • Hruby, V.J.1    Li, G.G.2    Haskell-Luevano, C.3    Shenderovich, M.4
  • 8
    • 0030768259 scopus 로고    scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1997) Tetrahedron , vol.53 , pp. 12789
    • Hanessian, S.1    McNaughton-Smith, G.2    Lombart, H.G.3    Lubell, W.D.4
  • 9
    • 15144354436 scopus 로고    scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1998) J. Med. Chem. , vol.41 , pp. 1581
    • Martin, S.F.1    Dorsey, G.O.2    Gane, T.3    Hillier, M.C.4    Kessler, H.5    Baur, M.6    Matha, B.7    Erickson, J.W.8    Bhat, T.N.9    Munshi, S.10    Gulnik, S.V.11    Topol, I.A.12
  • 10
    • 0031678366 scopus 로고    scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1998) Mol. Biotechnol. , vol.9 , pp. 205
    • Al-Obeidi, E.1    Hruby, V.J.2    Sawyer, T.K.3
  • 11
    • 0032133429 scopus 로고    scopus 로고
    • Reviews: (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357. (b) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bos, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039. (c) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 327. (d) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699. (e) Hruby, V. J.; Li, G. G.; Haskell- Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219. (f) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789. (g) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581. (h) Al-Obeidi, E.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205. (i) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441.
    • (1998) Curr. Opin. Chem. Biol. , vol.2 , pp. 441
    • Ripka, A.S.1    Rich, D.H.2
  • 26
    • 0000515280 scopus 로고
    • Ariens, E. J., Ed.; Academic: New York
    • (b) Rudinger, J. In Drug Design; Ariens, E. J., Ed.; Academic: New York, 1971; Vol. 2, p 319.
    • (1971) Drug Design , vol.2 , pp. 319
    • Rudinger, J.1
  • 27
    • 0344198789 scopus 로고
    • Ph.D. Thesis, University of Pennsylvania
    • Guzman, M. C. Ph.D. Thesis, University of Pennsylvania, 1995.
    • (1995)
    • Guzman, M.C.1
  • 39
    • 0033168016 scopus 로고    scopus 로고
    • Todd, J. A.; Acha-Orbea, H.; Bell, J. I.; Chao, N.; Fronek, Z.; Jacob, C. O.; McDermott, M.; Sinha, A. A.; Timmerman, L.; Steinman, L.; McDevitt, H. O. Science 1988, 240, 1003. Seebach has recently described the synthesis and binding affinity of β-amino acid containing ligands for class I MHC proteins: Poenaru, S.; Lamas, J. R.; Folkers, G.; de Castro, J. A. L.; Seebach, D.; Rognan, D. J. Med. Chem. 1999, 42, 2318.
    • (1999) J. Med. Chem. , vol.42 , pp. 2318
    • Poenaru, S.1    Lamas, J.R.2    Folkers, G.3    De Castro, J.A.L.4    Seebach, D.5    Rognan, D.6
  • 42
    • 0031568787 scopus 로고    scopus 로고
    • (b) Stern, L. J.; Brown, J. H.; Jardetzky, T. S.; Gorga, J. C.; Urban, R. G.; Strominger, J. L.; Wiley: D. C. Nature 1994, 368, 215. See also: Jardetzky, T. Structure 1997, 5, 159.
    • (1997) Structure , vol.5 , pp. 159
    • Jardetzky, T.1
  • 44
    • 0028313992 scopus 로고
    • Nelson, C. A.; Petzold, S. J.; Unanue, E. R. Nature 1994, 371, 250. Review: Cresswell, P. Annu. Rev. Immunol. 1994, 12, 259.
    • (1994) Annu. Rev. Immunol. , vol.12 , pp. 259
    • Cresswell, P.1
  • 45
    • 0001339532 scopus 로고
    • This figure was generated using Molscript (Kraulis, P. J. J. Appl. Crystallogr. 1991, 24, 946) and Raster 3D (Bacon, D., Anderson, W. F. J. Mol. Graph. 1988, 6, 219; Merritt, E. A.; Murphy, M. E. P. Acta Crystallogr. 1994, D50, 869.).
    • (1991) J. Appl. Crystallogr. , vol.24 , pp. 946
    • Kraulis, P.J.1
  • 46
    • 0000913086 scopus 로고
    • This figure was generated using Molscript (Kraulis, P. J. J. Appl. Crystallogr. 1991, 24, 946) and Raster 3D (Bacon, D., Anderson, W. F. J. Mol. Graph. 1988, 6, 219; Merritt, E. A.; Murphy, M. E. P. Acta Crystallogr. 1994, D50, 869.).
    • (1988) J. Mol. Graph. , vol.6 , pp. 219
    • Bacon, D.1    Anderson, W.F.2
  • 47
    • 0028057108 scopus 로고
    • This figure was generated using Molscript (Kraulis, P. J. J. Appl. Crystallogr. 1991, 24, 946) and Raster 3D (Bacon, D., Anderson, W. F. J. Mol. Graph. 1988, 6, 219; Merritt, E. A.; Murphy, M. E. P. Acta Crystallogr. 1994, D50, 869.).
    • (1994) Acta Crystallogr. , vol.D50 , pp. 869
    • Merritt, E.A.1    Murphy, M.E.P.2
  • 52
    • 0345492619 scopus 로고    scopus 로고
    • Hoffmann-La Roche Inc., unpublished results
    • (b) Bolin, D.; Campbell, R. Hoffmann-La Roche Inc., unpublished results.
    • Bolin, D.1    Campbell, R.2
  • 59
    • 0345061043 scopus 로고    scopus 로고
    • note
    • 4e as illustrated below: equation presented
  • 76
    • 0345492613 scopus 로고    scopus 로고
    • DuPont Pharmaceutical, Personal communication
    • Nugiel, D. A., DuPont Pharmaceutical, Personal communication.
    • Nugiel, D.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.