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Volumn 126, Issue 32, 2004, Pages 9878-9879

Guanidinium groups act as general-acid catalysts in phosphoryl transfer reactions: A two-proton inventory on a model system

Author keywords

[No Author keywords available]

Indexed keywords

2 GUANIDINYLMETHYLPHENOL; 2 HYDROXYPROPYL 4 NITROPHENYL PHOSPHATE; ALCOHOL; AMMONIA; AMMONIUM DERIVATIVE; ARGININE; COORDINATION COMPOUND; ETHER DERIVATIVE; GLUTAMIC ACID; GUANIDINE; GUANIDINE DERIVATIVE; HISTIDINE; HYDROGEN PEROXIDE; IMIDAZOLE DERIVATIVE; LYSINE; OXYGEN; PHOSPHATE; PHOSPHODIESTER; PHOSPHORANE DERIVATIVE; PHOSPHORUS DERIVATIVE; RIBONUCLEASE A; UNCLASSIFIED DRUG; WATER;

EID: 4043055019     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046894v     Document Type: Article
Times cited : (58)

References (35)
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    • (a) Raines, R. T. Chem. Rev. 1998, 98, 1045-1066.
    • (1998) Chem. Rev. , vol.98 , pp. 1045-1066
    • Raines, R.T.1
  • 19
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    • Lopez, X.; Schaefer, M.; Dejaegere, A.; Karplus, M. J. Am. Chem. Soc. 2002, 124, 5010-5018. (b) Davies, J. E.; Doltsinis, N. L.; Kirby, A. J.; Roussev, C. D.; Sprik, M. J. Am. Chem. Soc. 2002, 124, 6594-6599.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5010-5018
    • Lopez, X.1    Schaefer, M.2    Dejaegere, A.3    Karplus, M.4
  • 22
    • 4043134744 scopus 로고    scopus 로고
    • note
    • For more references see Supporting Information.
  • 30
    • 4043180057 scopus 로고    scopus 로고
    • note
    • 2 + 0.3314n, ref 10a.
  • 31
    • 4043051119 scopus 로고    scopus 로고
    • note
    • To our knowledge a proton inventory on this structure has not been previously reported.
  • 32
    • 33845184717 scopus 로고
    • LG values have been measured for phosphoryl transfer from RNA analogues, all in the range used here. (a) Herschalg, D.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7587-7596.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7587-7596
    • Herschalg, D.1    Jencks, W.P.2
  • 35
    • 0036091739 scopus 로고    scopus 로고
    • (c) In an alkylester, rather than an aryl ester, leaving-group departure may be rate limiting and require a subsequent protonation step. This would potentially mask the rate enhancement found for 1. Mikkola, S.; Kosonen, M.; Lönnberg, H. Curr. Org. Chem. 2002, 6, 523-538.
    • (2002) Curr. Org. Chem. , vol.6 , pp. 523-538
    • Mikkola, S.1    Kosonen, M.2    Lönnberg, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.