Mechanism for Acid-Catalyzed Hydrolysis of Nucleoside and Acyclonucleoside Analogues of Benzimidazole
作者： Mikko Oivanen , Harri Lönnberg , Zygmunt Kazimierczuk , David Shugar
DOI: 10.1080/07328318908054162
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摘要: Abstract A study has been made of a broad series nucleosides and acyclonucleosides variety benzimidazole analogues. Quantitative kinetic data are presented, the mechanism reactions described, taking into account steric, electronic conformational effects. The overall results also compared with those purine nucleosides.
sci-hub.se 参考文章(30)
Zygmunt Kazimierczuk, David Shugar, Ryszard Stolarski, Acyclonucleosides: acyclobenzimidazole nucleoside and nucleotide analogues and conformations of the acyclic chains by means of NMR spectroscopy. Acta Biochimica Polonica. ,vol. 31, pp. 33- 48 ,(1984)
John Anthony MacPhee, Annick Panaye, Jacques-Emile Dubois, Steric effects—I Tetrahedron. ,vol. 34, pp. 3553- 3562 ,(1978) , 10.1016/0040-4020(78)88431-2
Pravinkumar B. Sehgal, Igor Tamm, Halogenated benzimidazole ribosides, Novel inhibitors of RNA synthesis. Biochemical Pharmacology. ,vol. 27, pp. 2475- 2485 ,(1978) , 10.1016/0006-2952(78)90313-1
Harri Lönnberg, Rainer Käppi, Mechanisms for the solvolytic decompositions of nucleoside analogues—I : Acidic hydrolysis of 2-substituted 1-(1-ethoxyethyl)benzimidazoles Tetrahedron. ,vol. 36, pp. 913- 918 ,(1980) , 10.1016/0040-4020(80)80042-1
M C Zandomeni, R Zandomeni, D Shugar, R Weinmann, Casein kinase type II is involved in the inhibition by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole of specific RNA polymerase II transcription. Journal of Biological Chemistry. ,vol. 261, pp. 3414- 3419 ,(1986) , 10.1016/S0021-9258(17)35799-X
M. Kapoor, E. R. Waygood, METABOLISM OF BENZIMIDAZOLE IN WHEAT: I. FORMATION OF BENZIMIDAZOLE NUCLEOTIDE Canadian Journal of Biochemistry. ,vol. 43, pp. 153- 164 ,(1965) , 10.1139/O65-022
Richard P. Crews, David C. Baker, Synthesis of 2′- and 3′-Ketoadenosines Nucleosides, Nucleotides & Nucleic Acids. ,vol. 2, pp. 275- 289 ,(1983) , 10.1080/07328318308078861
Raymond P. Panzica, Robert J. Rousseau, Roland K. Robins, Leroy B. Townsend, A study on the relative stability and a quantitative appraoch to the reaction mechanism of the acid-catalyzed hydrolysis of certain7-and9- -D-ribofuranosylpurines. Journal of the American Chemical Society. ,vol. 94, pp. 4708- 4714 ,(1972) , 10.1021/JA00768A045
Frank Seela, Sabine Menkhoff, Silvia Behrendt, Furanoside–pyranoside isomerization of tubercidin and its 2′-deoxy derivatives: influence of nucleobase and sugar structure on the proton-catalysed reaction Journal of The Chemical Society-perkin Transactions 1. ,vol. 17, pp. 525- 530 ,(1986) , 10.1039/P29860000525
Robert A. Coburn, Michael T. Clark, Richard T. Evans, Robert J. Genco, Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases. Journal of Medicinal Chemistry. ,vol. 30, pp. 205- 208 ,(1987) , 10.1021/JM00384A035