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Volumn 118, Issue 28, 1996, Pages 6588-6600

Further studies on the buffer-catalyzed cleavage and isomerization of uridyluridine. Medium and ionic strength effects on catalysis by morpholine, imidazole, and acetate buffers help clarify the mechanisms involved and their relationship to the mechanism used by the enzyme ribonuclease and by a ribonuclease mimic

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE; MORPHOLINE; RIBONUCLEASE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE; URIDYLURIDINE;

EID: 0030010889     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9526933     Document Type: Article
Times cited : (70)

References (37)
  • 10
    • 0003956918 scopus 로고
    • McGraw-Hill Book Company: New York
    • Much ado has been made about our use of the phrase "negative catalysis". This term was first used by L. P. Hammett (Physical Organic Chemistry, 1st ed.; McGraw-Hill Book Company: New York, 1940: p 398). It simply means that a species that is functioning as a catalyst (i.e., it is not changed at the end of the reaction, and it is not simply an inhibitor of another catalyst) is observed to slow a reaction. Of course it does it by speeding another reaction in a branching process. I do not retract the use of this perfectly apt phrase by us or by Hammett.
    • (1940) Physical Organic Chemistry, 1st Ed. , pp. 398
    • Hammett, L.P.1
  • 13
    • 8944239944 scopus 로고    scopus 로고
    • note
    • First suggested by Charles Perrin as an anonymous referee of ref 12.
  • 28
    • 0000223524 scopus 로고
    • Haim
    • Haim (Haim, A. J. Am. Chem. Soc. 1992, 114, 8384-8388) argued that the isomerization and cleavage reactions did not proceed through a common intermediate. Our conclusion is that this could be partly correct: the cleavage reaction has an additional path that may bypass the isomerization intermediate 5 - unless it involves the scheme of Figure 11 - as well as the one that passes through it.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 8384-8388
    • Haim, A.1
  • 29
    • 37049072666 scopus 로고
    • Kosonen and Lönnberg
    • Kosonen and Lönnberg (Kosonen, M.; Lönnberg, H. J. Chem. Soc., Perkin Trans. 2 1995, 1203-1209) describe relevant studies on the cleavage and isomerization of a uridine phosphate triester. Since their intermediate phosphorane anion does not carry a proton, it cannot show the base-catalyzed decomposition we invoke for our cases.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 1203-1209
    • Kosonen, M.1    Lönnberg, H.2
  • 31
    • 0004039292 scopus 로고
    • Boyer, P. D., Ed.; Academic Press: New York
    • For reviews, see: (a) Richards, F. M.; Wyckoff, H. W. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1971 ; Vol. 4. (b) Blackburn, P.; Moore, S. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1982; Vol. 15. (c) Campbell, C. L.; Petsko, G. A. Biochemistry 1987, 26, 8579-8584 and references cited therein.
    • (1971) The Enzymes , vol.4
    • Richards, F.M.1    Wyckoff, H.W.2
  • 32
    • 0004284357 scopus 로고
    • Boyer, P. D., Ed.; Academic Press: New York
    • For reviews, see: (a) Richards, F. M.; Wyckoff, H. W. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1971 ; Vol. 4. (b) Blackburn, P.; Moore, S. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1982; Vol. 15. (c) Campbell, C. L.; Petsko, G. A. Biochemistry 1987, 26, 8579-8584 and references cited therein.
    • (1982) The Enzymes , vol.15
    • Blackburn, P.1    Moore, S.2
  • 33
    • 0023631047 scopus 로고
    • and references cited therein
    • For reviews, see: (a) Richards, F. M.; Wyckoff, H. W. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1971 ; Vol. 4. (b) Blackburn, P.; Moore, S. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1982; Vol. 15. (c) Campbell, C. L.; Petsko, G. A. Biochemistry 1987, 26, 8579-8584 and references cited therein.
    • (1987) Biochemistry , vol.26 , pp. 8579-8584
    • Campbell, C.L.1    Petsko, G.A.2


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