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Volumn 40, Issue 22, 1997, Pages 3551-3556

Discovery of 3-aminobenzyloxycarbonyl as an N-terminal group conferring high affinity to the minimal phosphopeptide sequence recognized by the Grb2- SH2 domain

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRANILIC ACID; PEPTIDE DERIVATIVE; PHOSPHOPEPTIDE;

EID: 0030725743     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9702185     Document Type: Article
Times cited : (60)

References (42)
  • 1
    • 0028097472 scopus 로고
    • Pharmaceutical Research in Molecular Oncology
    • Gibbs, J. B.; Oliff, A. Pharmaceutical Research in Molecular Oncology. Cell 1994, 79, 193-198.
    • (1994) Cell , vol.79 , pp. 193-198
    • Gibbs, J.B.1    Oliff, A.2
  • 2
    • 0030294380 scopus 로고    scopus 로고
    • Targeting Signal Transduction in the Discovery of Antiproliferative Drugs
    • Saltiel, A. R; Sawyer, T. K. Targeting Signal Transduction in the Discovery of Antiproliferative Drugs. Chem. Biol. 1996, 3, 887-893.
    • (1996) Chem. Biol. , vol.3 , pp. 887-893
    • Saltiel, A.R.1    Sawyer, T.K.2
  • 3
    • 0028000069 scopus 로고
    • Signal Transduction Therapy. A Novel Approach to Disease Management
    • Levitzki, A. Signal Transduction Therapy. A Novel Approach to Disease Management. Eur. J. Biochem. 1994, 226, 1-13.
    • (1994) Eur. J. Biochem. , vol.226 , pp. 1-13
    • Levitzki, A.1
  • 4
    • 0029688431 scopus 로고    scopus 로고
    • Protein Tyrosine Kinase Inhibitors
    • Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Science B. V.: Amsterdam
    • Groundwater, P. W.; Solomons, K. R. H.; Drewe, J. A.; Munawar, M. A. Protein Tyrosine Kinase Inhibitors. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Science B. V.: Amsterdam, 1996; Vol. 33, pp 233-329.
    • (1996) Progress in Medicinal Chemistry , vol.33 , pp. 233-329
    • Groundwater, P.W.1    Solomons, K.R.H.2    Drewe, J.A.3    Munawar, M.A.4
  • 5
    • 0029556753 scopus 로고
    • Recent Advances in Protein Tyrosine Kinase Inhibitors
    • Traxler, P.; Lydon, N. Recent Advances in Protein Tyrosine Kinase Inhibitors. Drugs Future 1995, 20, 1261-1274.
    • (1995) Drugs Future , vol.20 , pp. 1261-1274
    • Traxler, P.1    Lydon, N.2
  • 6
    • 77956819926 scopus 로고
    • Tyrosine Kinase Induced Mitogenesis Breaking the Link with Cancer
    • Bristol, J. A., Ed.; Academic Press: San Diego
    • Gishizky, M. L. Tyrosine Kinase Induced Mitogenesis Breaking the Link with Cancer. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: San Diego, 1995; Vol. 30, pp 247-253.
    • (1995) Annual Reports in Medicinal Chemistry , vol.30 , pp. 247-253
    • Gishizky, M.L.1
  • 7
    • 0028895156 scopus 로고
    • SH2 and SH3 Domains: Potential Targets for Anti-Cancer Drug Design
    • Smithgall, T. E. SH2 and SH3 Domains: Potential Targets for Anti-Cancer Drug Design. J. Pharmacol. Toxicol. Methods 1995, 34, 125-132.
    • (1995) J. Pharmacol. Toxicol. Methods , vol.34 , pp. 125-132
    • Smithgall, T.E.1
  • 9
    • 0029861248 scopus 로고    scopus 로고
    • Controlling Epidermal Growth Factor (EGF)-stimulated Ras Activation in Intacts Cells by a Cell-permeable Peptide Mimicking Phosphorylated EGF Receptor
    • Rojas, M.; Yao, S. Y.; Lin, Y. Z. Controlling Epidermal Growth Factor (EGF)-stimulated Ras Activation in Intacts Cells by a Cell-permeable Peptide Mimicking Phosphorylated EGF Receptor. J. Biol. Chem. 1996, 272, 27456-27461.
    • (1996) J. Biol. Chem. , vol.272 , pp. 27456-27461
    • Rojas, M.1    Yao, S.Y.2    Lin, Y.Z.3
  • 10
    • 9844254209 scopus 로고    scopus 로고
    • Novartis Pharma Inc., Oncology Research Department, unpublished results
    • Peptide studies have established that the minimal sequence retaining micromolar affinity for the Grb2-SH2 domain is the tripeptide pTyr-Ile-Asn. Asparagine at position pTyr+2 is absolutely required while the pTyr+1 position is more versatile, valine, glutamine and glutamic acid being good substitutes for isoleucine (Garcia-Echeverria, C.; et al. Novartis Pharma Inc., Oncology Research Department, unpublished results).
    • Garcia-Echeverria, C.1
  • 12
    • 0027502504 scopus 로고
    • Tructure of the Regulatory Domains of the Src-Family Tyrosine Kinase Lck
    • Eck, M. J.; Shoelson, S. E.; Harrison, S. C. Structure of the Regulatory Domains of the Src-Family Tyrosine Kinase Lck. Nature 1993, 362, 87-91.
    • (1993) Nature , vol.362 , pp. 87-91
    • Eck, M.J.1    Shoelson, S.E.2    Harrison, S.C.S.3
  • 13
    • 0027732861 scopus 로고
    • Closing in on SH2 Specificity
    • Birge, R. B.; Hanafusa, H. Closing in on SH2 Specificity. Science 1993, 262, 1522-1524.
    • (1993) Science , vol.262 , pp. 1522-1524
    • Birge, R.B.1    Hanafusa, H.2
  • 14
    • 9844240236 scopus 로고    scopus 로고
    • Ligand residues are numbered relative to the position of the phosphotyrosine which is denoted pTyr 0
    • Ligand residues are numbered relative to the position of the phosphotyrosine which is denoted pTyr 0.
  • 17
    • 0028354446 scopus 로고
    • Nuclear Magnetic Resonance Structure of an SH2 Domain of Phospholipase C-g1 Complexed with a High Affinity Binding Peptide
    • Pascal, S. M.; Singer, A. U.; Gish, G; Yamazaki, T.; Shoelson, S. E.; Pawson, T.; Kay, L. E.; Forman-Kay, J. D. Nuclear Magnetic Resonance Structure of an SH2 Domain Of Phospholipase C-g1 Complexed with a High Affinity Binding Peptide. Cell 1994, 77, 461-472.
    • (1994) Cell , vol.77 , pp. 461-472
    • Pascal, S.M.1    Singer, A.U.2    Gish, G.3    Yamazaki, T.4    Shoelson, S.E.5    Pawson, T.6    Kay, L.E.7    Forman-Kay, J.D.8
  • 18
    • 0028773467 scopus 로고
    • Crystal Structures of Peptide Complexes of the Amino-Terminal SH2 Domain of the Syp Tyrosine Phosphatase
    • Lee, C. H.; Kominos, D.; Jacques, S.; Margolis, B.; Schlessinger, J.; Shoelson, S. E.; Kuriyan, J. Crystal Structures of Peptide Complexes of the Amino-Terminal SH2 Domain of the Syp Tyrosine Phosphatase. Structure 1994, 2, 423-438.
    • (1994) Structure , vol.2 , pp. 423-438
    • Lee, C.H.1    Kominos, D.2    Jacques, S.3    Margolis, B.4    Schlessinger, J.5    Shoelson, S.E.6    Kuriyan, J.7
  • 20
    • 0029894672 scopus 로고    scopus 로고
    • Structure of a Specific Peptide Complex of the Carboxy-Terminal SH2 Domain from the p85a Subunit of Phosphatidylinositol 3-Kinase
    • Breeze, A. L.; Kara, B. V.; Barratt, D. G.; Andersen, M.; Smith, J. C.; Luke, R.W.; Best, J. R.; Cartlidge, S. A. Structure of a Specific Peptide Complex of the Carboxy-Terminal SH2 Domain from the p85a Subunit of Phosphatidylinositol 3-Kinase. EMBO J. 1996, 15, 3579-3589.
    • (1996) EMBO J. , vol.15 , pp. 3579-3589
    • Breeze, A.L.1    Kara, B.V.2    Barratt, D.G.3    Andersen, M.4    Smith, J.C.5    Luke, R.W.6    Best, J.R.7    Cartlidge, S.A.8
  • 21
    • 9844240781 scopus 로고    scopus 로고
    • For the nomenclature of the SH2 domain residues, see ref 12 or 18
    • For the nomenclature of the SH2 domain residues, see ref 12 or 18.
  • 24
    • 0028153795 scopus 로고
    • Planar Stacking Interactions of Arginine and Aromatic Side-Chains in Proteins
    • Flocco, M. M.; Mowbray, S. L. Planar Stacking Interactions of Arginine and Aromatic Side-Chains in Proteins. J. Mol. Biol. 1994, 235, 709-717.
    • (1994) J. Mol. Biol. , vol.235 , pp. 709-717
    • Flocco, M.M.1    Mowbray, S.L.2
  • 25
    • 0028301445 scopus 로고
    • Amino/Aromatic Interactions in Proteins: Is the Evidence Stacked Against Hydrogen Bonding?
    • Mitchell, J. B. O.; Nandi, C. L.; McDonald, I. K.; Thornton, J. M.; Price, S. L. Amino/Aromatic Interactions in Proteins: Is the Evidence Stacked Against Hydrogen Bonding? J. Mol. Biol. 1994, 239, 315-331.
    • (1994) J. Mol. Biol. , vol.239 , pp. 315-331
    • Mitchell, J.B.O.1    Nandi, C.L.2    McDonald, I.K.3    Thornton, J.M.4    Price, S.L.5
  • 27
    • 0027175566 scopus 로고
    • Synthesis of Phosphotyrosine-Containing Peptides as Their Use as Substrates for Protein Tyrosine Phosphatases
    • Ottinger, E. A.; Shekels, L. L.; Bemlohr, D. A.; Barany, G. Synthesis of Phosphotyrosine-Containing Peptides as Their Use as Substrates for Protein Tyrosine Phosphatases. Biochemistry 1993, 32, 4354-4361.
    • (1993) Biochemistry , vol.32 , pp. 4354-4361
    • Ottinger, E.A.1    Shekels, L.L.2    Bemlohr, D.A.3    Barany, G.4
  • 28
    • 45949123116 scopus 로고
    • Solid-Phase Synthesis of Protected Peptide Fragments Using a Trialfcoxy-diphenyl-methylester resin
    • Rink, H. Solid-Phase Synthesis of Protected Peptide Fragments Using a Trialfcoxy-diphenyl-methylester resin. Tetrahedron Lett. 1987, 28, 3787-3790.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3787-3790
    • Rink, H.1
  • 30
    • 49549139072 scopus 로고
    • Reactifs de couplage peptidique IV (1) - L' hexafluorophosphate de benzotriazolyl N-oxytrisdi methyl amino phosphonium (B.O.P.)
    • (a) Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Reactifs de couplage peptidique IV (1) - L' hexafluorophosphate de benzotriazolyl N-oxytrisdi methyl amino phosphonium (B.O.P.). Tetrahedron Lett. 1975, 14, 1219-1922.
    • (1975) Tetrahedron Lett. , vol.14 , pp. 1219-1922
    • Castro, B.1    Dormoy, J.R.2    Evin, G.3    Selve, C.4
  • 31
    • 0014704672 scopus 로고
    • Eine neue methode zur synthese von peptiden: Aktivierung der caboxylgruppe mit dicyclohexylcarbodiimid unter zusatz von 1-hydoxy-benzotriazolen
    • (b) König, W.; Geiger, R. Eine neue methode zur synthese von peptiden: aktivierung der caboxylgruppe mit dicyclohexylcarbodiimid unter zusatz von 1-hydoxy-benzotriazolen. Chem. Ber. 1970, 103, 788-798.
    • (1970) Chem. Ber. , vol.103 , pp. 788-798
    • König, W.1    Geiger, R.2
  • 32
    • 12044258245 scopus 로고
    • 1-Hydroxy-7-azabenzotriazole. An Efficient Peptide Coupling Additive
    • Carpino, L. A. 1-Hydroxy-7-azabenzotriazole. An Efficient Peptide Coupling Additive. J. Am. Chem. Soc. 1993, 115, 4397-4398.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397-4398
    • Carpino, L.A.1
  • 33
    • 0025032015 scopus 로고
    • Preparation and Application of the 5-(4-(9-fluorenylmethyloxycarbonyl)aminopmethyl-3,5-dimethoxyphenoxy)-valeric Acid (PAL) Handle for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions
    • Albericio, F.; Kneib-Cordonier, N.; Biancalana, S.; Gera, L.; Masada, R. I.; Hudson, D.; Barany, G. Preparation and Application of the 5-(4-(9-fluorenylmethyloxycarbonyl)aminopmethyl-3,5-dimethoxyphenoxy)-valeric Acid (PAL) Handle for the Solid-Phase Synthesis of C-Terminal Peptide Amides under Mild Conditions. J. Org. Chem. 1990, 55, 3730-3743.
    • (1990) J. Org. Chem. , vol.55 , pp. 3730-3743
    • Albericio, F.1    Kneib-Cordonier, N.2    Biancalana, S.3    Gera, L.4    Masada, R.I.5    Hudson, D.6    Barany, G.7
  • 37
    • 0043162336 scopus 로고
    • An Internal Coordinate Monte Carlo Method for Searching Conformational Space
    • Chang, G.; Guida, W. C.; Still, W. C. An Internal Coordinate Monte Carlo Method for Searching Conformational Space. J. Am. Chem. Soc. 1989, 111, 4379-4386.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4379-4386
    • Chang, G.1    Guida, W.C.2    Still, W.C.3
  • 38
    • 0024685828 scopus 로고    scopus 로고
    • A Rapid Method for the Computation, Comparison and display of Molecular Volumes
    • "In-house" addition to MacroModel: (a) Bohacek, R. S.; Guida, W. C. A Rapid Method for the Computation, Comparison and display of Molecular Volumes. J. Mol. Graph. 1989, 7, 113-117. (b) Eyraud, V.; Dietrich, A. Novartis Pharma Inc. Unpublished results.
    • (1989) J. Mol. Graph. , vol.7 , pp. 113-117
    • Bohacek, R.S.1    Guida, W.C.2
  • 39
    • 0024685828 scopus 로고    scopus 로고
    • Novartis Pharma Inc. Unpublished results
    • "In-house" addition to MacroModel: (a) Bohacek, R. S.; Guida, W. C. A Rapid Method for the Computation, Comparison and display of Molecular Volumes. J. Mol. Graph. 1989, 7, 113-117. (b) Eyraud, V.; Dietrich, A. Novartis Pharma Inc. Unpublished results.
    • Eyraud, V.1    Dietrich, A.2
  • 40
    • 24444468650 scopus 로고
    • Ground States of Molecules. 38. The MNDO Method. Approximation and Parameters
    • Dewar, M. J. S.; Thiel, W. Ground States of Molecules. 38. The MNDO Method. Approximation and Parameters. J. Am. Chem. Soc. 1977, 99, 4899-4907.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4899-4907
    • Dewar, M.J.S.1    Thiel, W.2
  • 41
    • 0025390935 scopus 로고
    • MOPAC. A Semiempirical Molecular Orbital Program
    • Stewart, J. J. P. MOPAC. A Semiempirical Molecular Orbital Program. J. Comput.-Aided. Mol. Des. 1990, 1, 1-105.
    • (1990) J. Comput.-Aided. Mol. Des. , vol.1 , pp. 1-105
    • Stewart, J.J.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.