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Nucleosides and Nucleotides Volume 8, 1989 - Issue 1
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Original Articles

Mechanism for Acid-Catalyzed Hydrolysis of Nucleoside and Acyclonucleoside Analogues of Benzimidazole

Mikko Oivanen Department of Chemistry, University of Turku, SF-20500, Turku, Finland
,
Harri Lönnberg Department of Chemistry, University of Turku, SF-20500, Turku, Finland
,
Zygmunt Kazimierczuk Departments of Biophysics, University of Warsaw, 02-089, Warsaw, Poland
&
David Shugar Departments of Biophysics, University of Warsaw, 02-089, Warsaw, Poland; Institute of Biochemistry and Biophysics, Polish Academy of Sciences, 02-532, Warsaw, Poland
Pages 133-144 | Received 20 Jan 1988, Published online: 24 Oct 2006

Citations (14)

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IgorA. Mikhailopulo, Zygmunt Kazimierczuk, AnatoliI. Zinchenko, VladimirN. Barai, ValeriaV. Romanova & LudmillaA. Eroshevskaya. (1995) Benzimidazoles in the Reaction of Enzymatic Transglycosylation. Nucleosides and Nucleotides 14:3-5, pages 477-480.
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JamesA. Linn & JamesL. Kelley. (1993) Synthesis of C-1′-Branched Acyclic Nucleosides. Nucleosides and Nucleotides 12:2, pages 199-213.
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Jari Hovinen, David Shugar & Harri Lönnberg. (1990) Acid-Catalyzed Hydrolysis of 2-Amino-9-(α-D-Ribofuranosyl)-purine and its Acyclo and 2-Methyl Analogues: Competition Between Depurination and Opening of the Imidazole Ring. Nucleosides and Nucleotides 9:5, pages 697-712.
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Articles from other publishers (11)

Noora Virtanen, Lauri Polari, Maria Välilä & Satu Mikkola. (2005) Kinetic solvent deuterium isotope effect in transesterification of RNA models. Journal of Physical Organic Chemistry 18:5, pages 385-397.
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B. S. Ermolinsky & S. N. Mikhailov. (2000) Periodate oxidation in chemistry of nucleic acids: Dialdehyde derivatives of nucleosides, nucleotides, and oligonucleotides (Review). Russian Journal of Bioorganic Chemistry 26:7, pages 429-449.
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Kristjan S. Gudmundsson, George A. Freeman, John C. Drach & Leroy B. Townsend. (2000) Synthesis of Fluorosugar Analogues of 2,5,6-Trichloro-1-(β- d -ribofuranosyl)benzimidazole as Antivirals with Potentially Increased Glycosidic Bond Stability . Journal of Medicinal Chemistry 43:12, pages 2473-2478.
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Michael P. Jensen & Jack Halpern. (1999) Dealkylation of Coenzyme B 12 and Related Organocobalamins:  Ligand Structural Effects on Rates and Mechanisms of Hydrolysis . Journal of the American Chemical Society 121:10, pages 2181-2192.
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Mikko Oivanen, Markku Rajamäki, Jaana Varila, Jari Hovinen, Sergey Mikhailov & Harri Lönnberg. (1994) Additional evidence for the exceptional mechanism of the acid-catalysed hydrolysis of 4-oxopyrimidine nucleosides: hydrolysis of 1-(1-alkoxyalkyl)uracils, seconucleosides, 3′-C-alkyl nucleosides and nucleoside 3′,5′-cyclic monophosphates. J. Chem. Soc., Perkin Trans. 2:2, pages 309-314.
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Gordon Shaw. 1994. Chemistry of Nucleosides and Nucleotides. Chemistry of Nucleosides and Nucleotides 263 420 .
Harri Hakala, Mikko Oivanen, Eija Saloniemi, Andrei Gouzaev & Harri Lönnberg. (2004) Acid‐catalysed depurination of DI‐, TRI‐ and polydeoxyribonucleotides: Effect of molecular environment on the cleavage of adenine residue. Journal of Physical Organic Chemistry 5:12, pages 824-828.
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Corine Glemarec, Yevgeny Besidsky, Jyoti Chattopadhyaya, Jaroslaw Kusmierek, Marjo Lahti, Mikko Oivanen & Harri Lönnberg. (1991) N23-ethenoguanosine and IA′-metamorphosine: 5N NMR Spectroscopy and elucidation of physico-chemical properties by kinetic and equilibrium measurements. Tetrahedron 47:33, pages 6689-6704.
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Rainer Käppi, Zygmunt Kazimierczuk, Pia Järvinen, Frank Seela & Harri Lönnberg. (1991) Kinetics and mechanism of the acid-catalysed hydrolysis of regioisomeric benzotriazole and 8-azaadenine nucleosides. J. Chem. Soc., Perkin Trans. 2:5, pages 595-600.
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J. Hovinen, C. Glemarec, A. Sandström, C. Sund & J. Chattopadhyaya. (1991) Spectroscopic, kinetic and semiempirical molecular orbital studies on 8-amino-, 8-methylamino- & 8-dimethylamino-adenosines. Tetrahedron 47:26, pages 4693-4708.
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Ajit Kumar & Richard T. Walker. (1990) The chemistry of 2',3'-seconucleosides IV. Synthesis and reactions of 3'-azido-2',3'-dideoxy-2',3'- secothymidine and related analogues. Tetrahedron 46:9, pages 3101-3110.
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