메뉴 건너뛰기




Volumn , Issue 10, 1997, Pages 2073-2081

Supramolecular catalysis of H/D exchange in pyruvate by macrocyclic polyamines involving a reactive iminium intermediate

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0344770006     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700937b     Document Type: Article
Times cited : (13)

References (73)
  • 3
    • 0004155427 scopus 로고
    • W. H. Freeman, New York, 3rd edn.
    • (c) L. Stryer, Biochemistry, W. H. Freeman, New York, 3rd edn., 1988;
    • (1988) Biochemistry
    • Stryer, L.1
  • 4
    • 0003458662 scopus 로고
    • Tetrahedron Organic Chemistry Series, Pergamon Press, Oxford
    • (d) C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry Series, vol. 12, Pergamon Press, Oxford, 1994, pp. 195-251;
    • (1994) Enzymes in Synthetic Organic Chemistry , vol.12 , pp. 195-251
    • Wong, C.-H.1    Whitesides, G.M.2
  • 14
    • 0347338588 scopus 로고
    • American Chemical Society, Washington, DC
    • (n) R. F. Gould, Bioorganic Chemistry, American Chemical Society, Washington, DC, 1971, pp. 390-412.
    • (1971) Bioorganic Chemistry , pp. 390-412
    • Gould, R.F.1
  • 18
    • 0003719912 scopus 로고
    • Springer Verlag, New York, 2nd edn.
    • (b) H. Dugas, Bioorganic Chemistry, Springer Verlag, New York, 2nd edn., 1989, p. 527;
    • (1989) Bioorganic Chemistry , pp. 527
    • Dugas, H.1
  • 41
    • 0000227183 scopus 로고
    • (a) J.-M. Lehn, Pure Appl. Chem., 1979, 51, 979; Ann. N. Y. Acad. Sci., 1986, 471, 41; Angew. Chem., Intl. Ed. Engl., 1988, 27, 89; Supramolecular Chemistry, VCH, Weinheim, 1995, ch. 5;
    • (1979) Pure Appl. Chem. , vol.51 , pp. 979
    • Lehn, J.-M.1
  • 42
    • 85016530969 scopus 로고
    • (a) J.-M. Lehn, Pure Appl. Chem., 1979, 51, 979; Ann. N. Y. Acad. Sci., 1986, 471, 41; Angew. Chem., Intl. Ed. Engl., 1988, 27, 89; Supramolecular Chemistry, VCH, Weinheim, 1995, ch. 5;
    • (1986) Ann. N. Y. Acad. Sci. , vol.471 , pp. 41
  • 43
    • 0003087010 scopus 로고
    • (a) J.-M. Lehn, Pure Appl. Chem., 1979, 51, 979; Ann. N. Y. Acad. Sci., 1986, 471, 41; Angew. Chem., Intl. Ed. Engl., 1988, 27, 89; Supramolecular Chemistry, VCH, Weinheim, 1995, ch. 5;
    • (1988) Angew. Chem., Intl. Ed. Engl. , vol.27 , pp. 89
  • 44
    • 0003699562 scopus 로고
    • VCH, Weinheim, ch. 5
    • (a) J.-M. Lehn, Pure Appl. Chem., 1979, 51, 979; Ann. N. Y. Acad. Sci., 1986, 471, 41; Angew. Chem., Intl. Ed. Engl., 1988, 27, 89; Supramolecular Chemistry, VCH, Weinheim, 1995, ch. 5;
    • (1995) Supramolecular Chemistry
  • 47
    • 0346708050 scopus 로고    scopus 로고
    • note
    • 10
  • 52
    • 0347338560 scopus 로고
    • J. Hine, F. E. Rogers and R. E. Notari, J. Am. Chem. Soc., 1968, 90, 3279; J. Hine, E. F. Glod, R. E. Notari, F. E. Rogers and F. C. Schmalstieg, J. Am. Chem. Soc., 1973, 95, 2537; J. Hine, M. S. Sholod and R. A. King, J. Am. Chem. Soc., 1974, 96, 835; J. Hine and R. L. Flachskam, Jr., J. Org. Chem., 1974, 39, 863; J. Hine and S. S. Ulrey, J. Org. Chem., 1974, 39, 3231; J. Hine, Acc. Chem. Res., 1978, 11, 1.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 3279
    • Hine, J.1    Rogers, F.E.2    Notari, R.E.3
  • 53
    • 0346077351 scopus 로고
    • J. Hine, F. E. Rogers and R. E. Notari, J. Am. Chem. Soc., 1968, 90, 3279; J. Hine, E. F. Glod, R. E. Notari, F. E. Rogers and F. C. Schmalstieg, J. Am. Chem. Soc., 1973, 95, 2537; J. Hine, M. S. Sholod and R. A. King, J. Am. Chem. Soc., 1974, 96, 835; J. Hine and R. L. Flachskam, Jr., J. Org. Chem., 1974, 39, 863; J. Hine and S. S. Ulrey, J. Org. Chem., 1974, 39, 3231; J. Hine, Acc. Chem. Res., 1978, 11, 1.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2537
    • Hine, J.1    Glod, E.F.2    Notari, R.E.3    Rogers, F.E.4    Schmalstieg, F.C.5
  • 54
    • 0010116210 scopus 로고
    • J. Hine, F. E. Rogers and R. E. Notari, J. Am. Chem. Soc., 1968, 90, 3279; J. Hine, E. F. Glod, R. E. Notari, F. E. Rogers and F. C. Schmalstieg, J. Am. Chem. Soc., 1973, 95, 2537; J. Hine, M. S. Sholod and R. A. King, J. Am. Chem. Soc., 1974, 96, 835; J. Hine and R. L. Flachskam, Jr., J. Org. Chem., 1974, 39, 863; J. Hine and S. S. Ulrey, J. Org. Chem., 1974, 39, 3231; J. Hine, Acc. Chem. Res., 1978, 11, 1.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 835
    • Hine, J.1    Sholod, M.S.2    King, R.A.3
  • 55
    • 0346708042 scopus 로고
    • J. Hine, F. E. Rogers and R. E. Notari, J. Am. Chem. Soc., 1968, 90, 3279; J. Hine, E. F. Glod, R. E. Notari, F. E. Rogers and F. C. Schmalstieg, J. Am. Chem. Soc., 1973, 95, 2537; J. Hine, M. S. Sholod and R. A. King, J. Am. Chem. Soc., 1974, 96, 835; J. Hine and R. L. Flachskam, Jr., J. Org. Chem., 1974, 39, 863; J. Hine and S. S. Ulrey, J. Org. Chem., 1974, 39, 3231; J. Hine, Acc. Chem. Res., 1978, 11, 1.
    • (1974) J. Org. Chem. , vol.39 , pp. 863
    • Hine, J.1    Flachskam R.L., Jr.2
  • 56
    • 0347968811 scopus 로고
    • J. Hine, F. E. Rogers and R. E. Notari, J. Am. Chem. Soc., 1968, 90, 3279; J. Hine, E. F. Glod, R. E. Notari, F. E. Rogers and F. C. Schmalstieg, J. Am. Chem. Soc., 1973, 95, 2537; J. Hine, M. S. Sholod and R. A. King, J. Am. Chem. Soc., 1974, 96, 835; J. Hine and R. L. Flachskam, Jr., J. Org. Chem., 1974, 39, 863; J. Hine and S. S. Ulrey, J. Org. Chem., 1974, 39, 3231; J. Hine, Acc. Chem. Res., 1978, 11, 1.
    • (1974) J. Org. Chem. , vol.39 , pp. 3231
    • Hine, J.1    Ulrey, S.S.2
  • 57
    • 0002735921 scopus 로고
    • J. Hine, F. E. Rogers and R. E. Notari, J. Am. Chem. Soc., 1968, 90, 3279; J. Hine, E. F. Glod, R. E. Notari, F. E. Rogers and F. C. Schmalstieg, J. Am. Chem. Soc., 1973, 95, 2537; J. Hine, M. S. Sholod and R. A. King, J. Am. Chem. Soc., 1974, 96, 835; J. Hine and R. L. Flachskam, Jr., J. Org. Chem., 1974, 39, 863; J. Hine and S. S. Ulrey, J. Org. Chem., 1974, 39, 3231; J. Hine, Acc. Chem. Res., 1978, 11, 1.
    • (1978) Acc. Chem. Res. , vol.11 , pp. 1
    • Hine, J.1
  • 64
    • 0000605895 scopus 로고
    • For an estimate of the lifetime of various iminium species, see: S. Eldin and W. P. Jencks, J. Am. Chem. Soc., 1995, 117, 4851.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4851
    • Eldin, S.1    Jencks, W.P.2
  • 65
    • 0346708040 scopus 로고    scopus 로고
    • note
    • 2O. The control experiment was performed under the same experimental conditions in the absence of 5.
  • 72
    • 0347968807 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy is the same within 5-10% in the absence and presence of 10. At pH 2, 3, 4, 5 and 6 the percentage of pyruvate in the hydrate form is respectively 57, 55, 33, 8 and 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.