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Helvetica Chimica Acta
Volumn 80, Issue 2, 1997, Pages 421-435
32. Stereochemistry of the Inhibition of δ-Chymotrypsin with Optically Active Bicyclic Organophosphates: 31P-NMR Studies
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EID: 0000025885     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19970800208     Document Type: Article
Times cited : (15)
References (68)
  • 1
    • 1542734183 scopus 로고
    • R. A. Osterbaan, P. Kunst, J. A. Cohn, Biochim. Biophys. Acta 1955, 16, 299; B. S. Hartley, Annu. Rev. Biochem. 1960, 29, 45; W. N. Aldrigde, E. Reiner, in 'Enzyme Inhibitors as Substrates: Interactions of Esterases with Organophosphorus and Carbamic Acids', American Elsevier, New York, 1972; R. M. Stroud, L. M. Kay, R. E. Dickerson, J. Mol. Biol. 1974, 83, 185; A. R. Main, Pharmacol. Ther. 1979, 6, 579; A. A. Kossiakoff, S. A. Spencer, Biochemistry 1981, 20, 6462.
    • (1955) Biochim. Biophys. Acta , vol.16 , pp. 299
    • Osterbaan, R.A.1    Kunst, P.2    Cohn, J.A.3
  • 2
    • 72949151819 scopus 로고
    • R. A. Osterbaan, P. Kunst, J. A. Cohn, Biochim. Biophys. Acta 1955, 16, 299; B. S. Hartley, Annu. Rev. Biochem. 1960, 29, 45; W. N. Aldrigde, E. Reiner, in 'Enzyme Inhibitors as Substrates: Interactions of Esterases with Organophosphorus and Carbamic Acids', American Elsevier, New York, 1972; R. M. Stroud, L. M. Kay, R. E. Dickerson, J. Mol. Biol. 1974, 83, 185; A. R. Main, Pharmacol. Ther. 1979, 6, 579; A. A. Kossiakoff, S. A. Spencer, Biochemistry 1981, 20, 6462.
    • (1960) Annu. Rev. Biochem. , vol.29 , pp. 45
    • Hartley, B.S.1
  • 3
    • 0004135623 scopus 로고
    • American Elsevier, New York
    • R. A. Osterbaan, P. Kunst, J. A. Cohn, Biochim. Biophys. Acta 1955, 16, 299; B. S. Hartley, Annu. Rev. Biochem. 1960, 29, 45; W. N. Aldrigde, E. Reiner, in 'Enzyme Inhibitors as Substrates: Interactions of Esterases with Organophosphorus and Carbamic Acids', American Elsevier, New York, 1972; R. M. Stroud, L. M. Kay, R. E. Dickerson, J. Mol. Biol. 1974, 83, 185; A. R. Main, Pharmacol. Ther. 1979, 6, 579; A. A. Kossiakoff, S. A. Spencer, Biochemistry 1981, 20, 6462.
    • (1972) Enzyme Inhibitors as Substrates: Interactions of Esterases with Organophosphorus and Carbamic Acids
    • Aldrigde, W.N.1    Reiner, E.2
  • 4
    • 0015946772 scopus 로고
    • R. A. Osterbaan, P. Kunst, J. A. Cohn, Biochim. Biophys. Acta 1955, 16, 299; B. S. Hartley, Annu. Rev. Biochem. 1960, 29, 45; W. N. Aldrigde, E. Reiner, in 'Enzyme Inhibitors as Substrates: Interactions of Esterases with Organophosphorus and Carbamic Acids', American Elsevier, New York, 1972; R. M. Stroud, L. M. Kay, R. E. Dickerson, J. Mol. Biol. 1974, 83, 185; A. R. Main, Pharmacol. Ther. 1979, 6, 579; A. A. Kossiakoff, S. A. Spencer, Biochemistry 1981, 20, 6462.
    • (1974) J. Mol. Biol. , vol.83 , pp. 185
    • Stroud, R.M.1    Kay, L.M.2    Dickerson, R.E.3
  • 5
    • 0018731624 scopus 로고
    • R. A. Osterbaan, P. Kunst, J. A. Cohn, Biochim. Biophys. Acta 1955, 16, 299; B. S. Hartley, Annu. Rev. Biochem. 1960, 29, 45; W. N. Aldrigde, E. Reiner, in 'Enzyme Inhibitors as Substrates: Interactions of Esterases with Organophosphorus and Carbamic Acids', American Elsevier, New York, 1972; R. M. Stroud, L. M. Kay, R. E. Dickerson, J. Mol. Biol. 1974, 83, 185; A. R. Main, Pharmacol. Ther. 1979, 6, 579; A. A. Kossiakoff, S. A. Spencer, Biochemistry 1981, 20, 6462.
    • (1979) Pharmacol. Ther. , vol.6 , pp. 579
    • Main, A.R.1
  • 6
    • 0019889789 scopus 로고
    • R. A. Osterbaan, P. Kunst, J. A. Cohn, Biochim. Biophys. Acta 1955, 16, 299; B. S. Hartley, Annu. Rev. Biochem. 1960, 29, 45; W. N. Aldrigde, E. Reiner, in 'Enzyme Inhibitors as Substrates: Interactions of Esterases with Organophosphorus and Carbamic Acids', American Elsevier, New York, 1972; R. M. Stroud, L. M. Kay, R. E. Dickerson, J. Mol. Biol. 1974, 83, 185; A. R. Main, Pharmacol. Ther. 1979, 6, 579; A. A. Kossiakoff, S. A. Spencer, Biochemistry 1981, 20, 6462.
    • (1981) Biochemistry , vol.20 , pp. 6462
    • Kossiakoff, A.A.1    Spencer, S.A.2
  • 7
    • 0002437303 scopus 로고
    • N. K. Schaffer, C. S. May, W. H. Summerson, J. Biol. Chem. 1953, 202, 67; D. M. Blow, J. J. Birktoft, B. S. Hartley, Nature (London) 1969, 221, 337; D. M. Blow, Acc. Chem. Res. 1976, 9, 145; L. Polgar, in 'Hydrolytic Enzymes', Eds. A. Neuenberger and K. Brocklehurst, Elsevier, Amsterdam, 1987.
    • (1953) J. Biol. Chem. , vol.202 , pp. 67
    • Schaffer, N.K.1    May, C.S.2    Summerson, W.H.3
  • 8
    • 0014689979 scopus 로고
    • N. K. Schaffer, C. S. May, W. H. Summerson, J. Biol. Chem. 1953, 202, 67; D. M. Blow, J. J. Birktoft, B. S. Hartley, Nature (London) 1969, 221, 337; D. M. Blow, Acc. Chem. Res. 1976, 9, 145; L. Polgar, in 'Hydrolytic Enzymes', Eds. A. Neuenberger and K. Brocklehurst, Elsevier, Amsterdam, 1987.
    • (1969) Nature (London) , vol.221 , pp. 337
    • Blow, D.M.1    Birktoft, J.J.2    Hartley, B.S.3
  • 9
    • 33847799412 scopus 로고
    • N. K. Schaffer, C. S. May, W. H. Summerson, J. Biol. Chem. 1953, 202, 67; D. M. Blow, J. J. Birktoft, B. S. Hartley, Nature (London) 1969, 221, 337; D. M. Blow, Acc. Chem. Res. 1976, 9, 145; L. Polgar, in 'Hydrolytic Enzymes', Eds. A. Neuenberger and K. Brocklehurst, Elsevier, Amsterdam, 1987.
    • (1976) Acc. Chem. Res. , vol.9 , pp. 145
    • Blow, D.M.1
  • 10
    • 0003687074 scopus 로고
    • Eds. A. Neuenberger and K. Brocklehurst, Elsevier, Amsterdam
    • N. K. Schaffer, C. S. May, W. H. Summerson, J. Biol. Chem. 1953, 202, 67; D. M. Blow, J. J. Birktoft, B. S. Hartley, Nature (London) 1969, 221, 337; D. M. Blow, Acc. Chem. Res. 1976, 9, 145; L. Polgar, in 'Hydrolytic Enzymes', Eds. A. Neuenberger and K. Brocklehurst, Elsevier, Amsterdam, 1987.
    • (1987) Hydrolytic Enzymes
    • Polgar, L.1
  • 11
    • 0002903441 scopus 로고
    • R. Wolfenden, Acc. Chem. Res. 1972, 5, 10; G. E. Lienhard, Science 1973, 180, 149.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 10
    • Wolfenden, R.1
  • 12
    • 0015924871 scopus 로고
    • R. Wolfenden, Acc. Chem. Res. 1972, 5, 10; G. E. Lienhard, Science 1973, 180, 149.
    • (1973) Science , vol.180 , pp. 149
    • Lienhard, G.E.1
  • 13
    • 0343056432 scopus 로고
    • Ed. R. G. Shulman, Academic Press, New York
    • J. L. Markley, in 'Biological Applications of Magnetic Resonance', Ed. R. G. Shulman, Academic Press, New York, 1979, p. 397; H. J. Vogel, in 'Phosphorus-31 NMR', Ed. D. G. Gorenstein, Academic Press, Orlando, 1984, p. 105; D. G. Gorenstein, Chem. Rev. 1987, 87, 1047; D. G. Gorenstein, Methods Enzymol. 1989, 177, 295.
    • (1979) Biological Applications of Magnetic Resonance , pp. 397
    • Markley, J.L.1
  • 14
    • 84990417762 scopus 로고
    • Ed. D. G. Gorenstein, Academic Press, Orlando
    • J. L. Markley, in 'Biological Applications of Magnetic Resonance', Ed. R. G. Shulman, Academic Press, New York, 1979, p. 397; H. J. Vogel, in 'Phosphorus-31 NMR', Ed. D. G. Gorenstein, Academic Press, Orlando, 1984, p. 105; D. G. Gorenstein, Chem. Rev. 1987, 87, 1047; D. G. Gorenstein, Methods Enzymol. 1989, 177, 295.
    • (1984) Phosphorus-31 NMR , pp. 105
    • Vogel, H.J.1
  • 15
    • 1542545189 scopus 로고
    • J. L. Markley, in 'Biological Applications of Magnetic Resonance', Ed. R. G. Shulman, Academic Press, New York, 1979, p. 397; H. J. Vogel, in 'Phosphorus-31 NMR', Ed. D. G. Gorenstein, Academic Press, Orlando, 1984, p. 105; D. G. Gorenstein, Chem. Rev. 1987, 87, 1047; D. G. Gorenstein, Methods Enzymol. 1989, 177, 295.
    • (1987) Chem. Rev. , vol.87 , pp. 1047
    • Gorenstein, D.G.1
  • 16
    • 0024799061 scopus 로고
    • J. L. Markley, in 'Biological Applications of Magnetic Resonance', Ed. R. G. Shulman, Academic Press, New York, 1979, p. 397; H. J. Vogel, in 'Phosphorus-31 NMR', Ed. D. G. Gorenstein, Academic Press, Orlando, 1984, p. 105; D. G. Gorenstein, Chem. Rev. 1987, 87, 1047; D. G. Gorenstein, Methods Enzymol. 1989, 177, 295.
    • (1989) Methods Enzymol. , vol.177 , pp. 295
    • Gorenstein, D.G.1
  • 17
    • 0002213875 scopus 로고
    • Ed. D. G. Gorenstein, Academic Press, Orlando'
    • D. G. Gorenstein in 'Phosphorus-31 NMR', Ed. D. G. Gorenstein, Academic Press, Orlando', 1984, p. 7; 'Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis', 'Methods in Stereochemical Analysis', Eds. J. G. Verkade and L. D. Quin, Verlag Chemie, Weinheim, 1987, Vol. 8.
    • (1984) Phosphorus-31 NMR , pp. 7
    • Gorenstein, D.G.1
  • 18
    • 0003670183 scopus 로고
    • 'Methods in Stereochemical Analysis', Verlag Chemie, Weinheim
    • D. G. Gorenstein in 'Phosphorus-31 NMR', Ed. D. G. Gorenstein, Academic Press, Orlando', 1984, p. 7; 'Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis', 'Methods in Stereochemical Analysis', Eds. J. G. Verkade and L. D. Quin, Verlag Chemie, Weinheim, 1987, Vol. 8.
    • (1987) Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis , vol.8
    • Verkade, J.G.1    Quin, L.D.2
  • 23
    • 0026100862 scopus 로고
    • N. S. Sampson, P. A. Bartlett, Biochemistry 1991, 30, 2255; R. Bone, N. S. Sampson, P. A. Bartlett, D. A. Agard, ibid. 1991, 30, 2263.
    • (1991) Biochemistry , vol.30 , pp. 2255
    • Sampson, N.S.1    Bartlett, P.A.2
  • 32
    • 0042071550 scopus 로고
    • Eds. E. J. Ariens, J. J. S. van Rensen and W. Welling, Elsevier, Amsterdam
    • L. P. A. de Jong, H.P. Benschop, in 'Stereoselectivity of Pesticides', Eds. E. J. Ariens, J. J. S. van Rensen and W. Welling, Elsevier, Amsterdam, 1988, p. 109.
    • (1988) Stereoselectivity of Pesticides , pp. 109
    • De Jong, L.P.A.1    Benschop, H.P.2
  • 33
    • 0017324044 scopus 로고
    • J. Kraut, Annu. Rev. Biochem. 1977, 46, 331; L. Polgar, 'Mechanisms of Protease Action', CRC Press, Boca Raton, 1989.
    • (1977) Annu. Rev. Biochem. , vol.46 , pp. 331
    • Kraut, J.1
  • 35
    • 1542628938 scopus 로고
    • Ph.D. Thesis, University of Zurich
    • F. A. Merckling, Ph.D. Thesis, University of Zurich 1993; F. A. Merckling, P. Rüedi, Chimia 1994, 48, 279.
    • (1993)
    • Merckling, F.A.1
  • 36
    • 0343064941 scopus 로고
    • F. A. Merckling, Ph.D. Thesis, University of Zurich 1993; F. A. Merckling, P. Rüedi, Chimia 1994, 48, 279.
    • (1994) Chimia , vol.48 , pp. 279
    • Merckling, F.A.1    Rüedi, P.2
  • 37
    • 0006606917 scopus 로고
    • J. G. Verkade, Phosphorus Sulfur 1976, 2, 251; B. E. Maryanoff, R. O. Hutchins, C. A. Maryanoff, Topics Stereochem. 1979, 11, 187.
    • (1976) Phosphorus Sulfur , vol.2 , pp. 251
    • Verkade, J.G.1
  • 39
    • 0000882153 scopus 로고
    • D. G. Gorenstein, R. Rowell, J. Am. Chem. Soc. 1979, 101, 4925; D. G. Gorenstein, R. Rowell, J. Findlay, ibid. 1980, 102, 5077; R. O. Day, D. G. Gorenstein, R. R. Holmes, Inorg. Chem. 1983, 22, 2192; K. Taira, K. Li, D. G. Gorenstein, Tetrahedron 1986, 42, 229.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 4925
    • Gorenstein, D.G.1    Rowell, R.2
  • 40
    • 0012820897 scopus 로고
    • D. G. Gorenstein, R. Rowell, J. Am. Chem. Soc. 1979, 101, 4925; D. G. Gorenstein, R. Rowell, J. Findlay, ibid. 1980, 102, 5077; R. O. Day, D. G. Gorenstein, R. R. Holmes, Inorg. Chem. 1983, 22, 2192; K. Taira, K. Li, D. G. Gorenstein, Tetrahedron 1986, 42, 229.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5077
    • Gorenstein, D.G.1    Rowell, R.2    Findlay, J.3
  • 41
    • 0343500854 scopus 로고
    • D. G. Gorenstein, R. Rowell, J. Am. Chem. Soc. 1979, 101, 4925; D. G. Gorenstein, R. Rowell, J. Findlay, ibid. 1980, 102, 5077; R. O. Day, D. G. Gorenstein, R. R. Holmes, Inorg. Chem. 1983, 22, 2192; K. Taira, K. Li, D. G. Gorenstein, Tetrahedron 1986, 42, 229.
    • (1983) Inorg. Chem. , vol.22 , pp. 2192
    • Day, R.O.1    Gorenstein, D.G.2    Holmes, R.R.3
  • 42
    • 6244253508 scopus 로고
    • D. G. Gorenstein, R. Rowell, J. Am. Chem. Soc. 1979, 101, 4925; D. G. Gorenstein, R. Rowell, J. Findlay, ibid. 1980, 102, 5077; R. O. Day, D. G. Gorenstein, R. R. Holmes, Inorg. Chem. 1983, 22, 2192; K. Taira, K. Li, D. G. Gorenstein, Tetrahedron 1986, 42, 229.
    • (1986) Tetrahedron , vol.42 , pp. 229
    • Taira, K.1    Li, K.2    Gorenstein, D.G.3
  • 48
    • 0001242480 scopus 로고
    • A. R. Main, W. C. Dauterman, Nature (London) 1963, 4880, 551; A. R. Main, Science 1964, 144, 992.
    • (1964) Science , vol.144 , pp. 992
    • Main, A.R.1
  • 49
    • 77956895752 scopus 로고
    • Ed. P. D. Boyer, Academic Press, New York
    • H. C. Froede, I. B. Wilson, in The Enzymes', 3rd edn., Ed. P. D. Boyer, Academic Press, New York, 1971, Vol. 5, p. 87; T. Selwood, S. R. Feaster, M. J. States, A. N. Pryor, D. M. Quinn, J. Am. Chem. Soc. 1993, 115, 10477.
    • (1971) The Enzymes', 3rd Edn. , vol.5 , pp. 87
    • Froede, H.C.1    Wilson, I.B.2
  • 51
    • 0002920388 scopus 로고
    • F. H. Westheimer, Acc. Chem. Res. 1968, 1, 70; R. F. Hudson, C. Brown, ibid. 1972, 5, 204; P. Gillepsie, F. Ramirez, I. Ugi, D. Marquarding, Angew. Chem. Int. Ed. 1973, 12, 109; S. Tripett, Pure Appl. Chem. 1974, 40, 595.
    • (1968) Acc. Chem. Res. , vol.1 , pp. 70
    • Westheimer, F.H.1
  • 52
    • 0000438022 scopus 로고
    • F. H. Westheimer, Acc. Chem. Res. 1968, 1, 70; R. F. Hudson, C. Brown, ibid. 1972, 5, 204; P. Gillepsie, F. Ramirez, I. Ugi, D. Marquarding, Angew. Chem. Int. Ed. 1973, 12, 109; S. Tripett, Pure Appl. Chem. 1974, 40, 595.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 204
    • Hudson, R.F.1    Brown, C.2
  • 54
    • 84943071959 scopus 로고
    • F. H. Westheimer, Acc. Chem. Res. 1968, 1, 70; R. F. Hudson, C. Brown, ibid. 1972, 5, 204; P. Gillepsie, F. Ramirez, I. Ugi, D. Marquarding, Angew. Chem. Int. Ed. 1973, 12, 109; S. Tripett, Pure Appl. Chem. 1974, 40, 595.
    • (1974) Pure Appl. Chem. , vol.40 , pp. 595
    • Tripett, S.1
  • 57
    • 0020397836 scopus 로고
    • F. Eckstein, P. J. Romaniuk, B. A. Connolly, Methods Enzymol. 1982, 87, 197; S. A. Buchwald, D. E. Hansen, A. Hassett, J. R. Knowles, ibid. 1982, 87, 279; G. Löwe, Ace. Chem. Res. 1983, 16, 244.
    • (1982) Methods Enzymol. , vol.87 , pp. 197
    • Eckstein, F.1    Romaniuk, P.J.2    Connolly, B.A.3
  • 58
    • 0020453401 scopus 로고
    • F. Eckstein, P. J. Romaniuk, B. A. Connolly, Methods Enzymol. 1982, 87, 197; S. A. Buchwald, D. E. Hansen, A. Hassett, J. R. Knowles, ibid. 1982, 87, 279; G. Löwe, Ace. Chem. Res. 1983, 16, 244.
    • (1982) Ibid. , vol.87 , pp. 279
    • Buchwald, S.A.1    Hansen, D.E.2    Hassett, A.3    Knowles, J.R.4
  • 59
    • 0001506296 scopus 로고
    • F. Eckstein, P. J. Romaniuk, B. A. Connolly, Methods Enzymol. 1982, 87, 197; S. A. Buchwald, D. E. Hansen, A. Hassett, J. R. Knowles, ibid. 1982, 87, 279; G. Löwe, Ace. Chem. Res. 1983, 16, 244.
    • (1983) Ace. Chem. Res. , vol.16 , pp. 244
    • Löwe, G.1
  • 63
    • 1542509854 scopus 로고
    • J. Sanchez Real, J. Pascual, An. Fis. Quim. 1953, 49B, 445; M. A. Febrer, P. Gomis, J. Pascual, ibid. 1964, 60, 671; P. Gomis Torne, Rev. Real. Acad. Cienc. Exactas, Fis. Natur. Madrid 1966, 60, 419; K. Chilina, U. Thomas, A. F. Tucci, K. D. Michael, C. M. Stevens, Biochemistry 1969, 8, 2846.
    • (1953) An. Fis. Quim. , vol.49 B , pp. 445
    • Sanchez Real, J.1    Pascual, J.2
  • 64
    • 1542419483 scopus 로고
    • J. Sanchez Real, J. Pascual, An. Fis. Quim. 1953, 49B, 445; M. A. Febrer, P. Gomis, J. Pascual, ibid. 1964, 60, 671; P. Gomis Torne, Rev. Real. Acad. Cienc. Exactas, Fis. Natur. Madrid 1966, 60, 419; K. Chilina, U. Thomas, A. F. Tucci, K. D. Michael, C. M. Stevens, Biochemistry 1969, 8, 2846.
    • (1964) An. Fis. Quim. , vol.60 , pp. 671
    • Febrer, M.A.1    Gomis, P.2    Pascual, J.3
  • 65
    • 1542419485 scopus 로고
    • J. Sanchez Real, J. Pascual, An. Fis. Quim. 1953, 49B, 445; M. A. Febrer, P. Gomis, J. Pascual, ibid. 1964, 60, 671; P. Gomis Torne, Rev. Real. Acad. Cienc. Exactas, Fis. Natur. Madrid 1966, 60, 419; K. Chilina, U. Thomas, A. F. Tucci, K. D. Michael, C. M. Stevens, Biochemistry 1969, 8, 2846.
    • (1966) Rev. Real. Acad. Cienc. Exactas, Fis. Natur. Madrid , vol.60 , pp. 419
    • Gomis Torne, P.1
  • 66
    • 0014546029 scopus 로고
    • J. Sanchez Real, J. Pascual, An. Fis. Quim. 1953, 49B, 445; M. A. Febrer, P. Gomis, J. Pascual, ibid. 1964, 60, 671; P. Gomis Torne, Rev. Real. Acad. Cienc. Exactas, Fis. Natur. Madrid 1966, 60, 419; K. Chilina, U. Thomas, A. F. Tucci, K. D. Michael, C. M. Stevens, Biochemistry 1969, 8, 2846.
    • (1969) Biochemistry , vol.8 , pp. 2846
    • Chilina, K.1    Thomas, U.2    Tucci, A.F.3    Michael, K.D.4    Stevens, C.M.5

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