CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2004, Vol. 76, No. 10, pp. 1869-1886

http://dx.doi.org/10.1351/pac200476101869

Acid-base properties of purine residues and the effect of metal ions: Quantification of rare nucleobase tautomers

H. Sigel

Department of Chemistry, Inorganic Chemistry, University of Basel, Spitalstrasse 51, CH-4056 Basel, Switzerland

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Shimada Hiroyuki, Fukao Taishi, Minami Hirotake, Ukai Masatoshi, Fujii Kentaro, Yokoya Akinari, Fukuda Yoshihiro, Saitoh Yuji: Structural changes of nucleic acid base in aqueous solution as observed in X-ray absorption near edge structure (XANES). Chemical Physics Letters 2014, 591, 137. <http://dx.doi.org/10.1016/j.cplett.2013.11.026>
  • Švorc Ľubomír, Kalcher Kurt: Modification-free electrochemical approach for sensitive monitoring of purine DNA bases: Simultaneous determination of guanine and adenine in biological samples using boron-doped diamond electrode. Sensors and Actuators B: Chemical 2014, 194, 332. <http://dx.doi.org/10.1016/j.snb.2013.12.104>
  • Shukla Manoj K., Leszczynski Jerzy: Tautomerism in nucleic acid bases and base pairs: a brief overview. WIREs Comput Mol Sci 2013, 3, 637. <http://dx.doi.org/10.1002/wcms.1145>
  • Blindauer Claudia A., Sigel Astrid, Operschall Bert P., Holý Antonin, Sigel Helmut: Extent of Intramolecular π Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and 1-[2-(Phosphonomethoxy)ethyl]cytosine (PMEC), a Relative of Antivirally Active Acyclic Nucleotide Analogues (Part 72) [1, 2]. Z. anorg. allg. Chem. 2013, 639, 1661. <http://dx.doi.org/10.1002/zaac.201300095>
  • Domínguez-Martín Alicia, García-Raso Ángel, Cabot Catalina, Choquesillo-Lazarte Duane, Pérez-Toro Inmaculada, Matilla-Hernández Antonio, Castiñeiras Alfonso, Niclós-Gutiérrez Juan: Structural insights on the molecular recognition patterns between N6-substituted adenines and N-(aryl-methyl)iminodiacetate copper(II) chelates. Journal of Inorganic Biochemistry 2013, 127, 141. <http://dx.doi.org/10.1016/j.jinorgbio.2013.02.002>
  • Domínguez-Martín Alicia, Choquesillo-Lazarte Duane, Dobado Jose A., Martínez-García Henar, Lezama Luis, González-Pérez Josefa M., Castiñeiras Alfonso, Niclós-Gutiérrez Juan: Structural Consequences of the N7 and C8 Translocation on the Metal Binding Behavior of Adenine. Inorg. Chem. 2013, 52, 1916. <http://dx.doi.org/10.1021/ic302147u>
  • Gómez-Coca Raquel B., Blindauer Claudia A., Sigel Astrid, Operschall Bert P., Holý Antonín, Sigel Helmut: Extent of Intramolecular π-Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and Several 2-Aminopurine Derivatives of the Antivirally Active Nucleotide Analog 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA). Chemistry & Biodiversity 2012, 9, 2008. <http://dx.doi.org/10.1002/cbdv.201200022>
  • Sigel Astrid, Operschall Bert P., Sigel Helmut: Steric guiding of metal ion binding to a purine residue by a non-coordinating amino group: Examplified by 9-[(2-phosphonomethoxy)ethyl]-2-aminopurine (PME2AP), an isomer of the antiviral nucleotide analogue 9-[(2-phosphonomethoxy)ethyl]adenine (PMEA), and by related compounds. Coord Rev 2012, 256, 260. <http://dx.doi.org/10.1016/j.ccr.2011.06.030>
  • Khanna Shruti, Verma Sandeep: Crystallographic Signatures of N6-Methoxyadenine Imino Tautomer–Silver Complexes. Crystal Growth & Design 2012, 12, 3025. <http://dx.doi.org/10.1021/cg300231r>
  • Mihály Tímea, Garijo Añorbe Marta, Albertí Francisca M., Sanz Miguel Pablo J., Lippert Bernhard: Multiple Metal Binding to the 9-Methyladenine Model Nucleobase Involving N1, N6, and N7: Discrete Di- and Trinuclear Species with Different Combinations of Monofunctional PdII and PtII Entities. Inorg. Chem. 2012, 51, 10437. <http://dx.doi.org/10.1021/ic301681f>
  • Natesan Senthil, Subramaniam Rajesh, Bergeron Charles, Balaz Stefan: Binding Affinity Prediction for Ligands and Receptors Forming Tautomers and Ionization Species: Inhibition of Mitogen-Activated Protein Kinase-Activated Protein Kinase 2 (MK2). J Med Chem 2012, 55, 2035. <http://dx.doi.org/10.1021/jm201217q>
  • Stasyuk Olga A., Szatyłowicz Halina, Krygowski Tadeusz M.: Effect of the H-Bonding on Aromaticity of Purine Tautomers. J Org Chern 2012, 77, 4035. <http://dx.doi.org/10.1021/jo300406r>
  • Kapinos  Larisa E., Operschall Bert P., Larsen Erik, Sigel Helmut: Understanding the Acid-Base Properties of Adenosine: The Intrinsic Basicities of N1, N3 and N7. Chemistry A European Journal 2011, 17, 8156. <http://dx.doi.org/10.1002/chem.201003544>
  • Rodríguez-Santiago Luis, Sodupe Mariona, Lippert Bernhard, Noguera Marc, Müller Barbara, Shen Wei-Zheng, Sanz Miguel Pablo J., Albertí Francisca M., van der Wijst Tushar: PtII Coordination to N1 of 9-Methylguanine: Why it Facilitates Binding of Additional Metal Ions to the Purine Ring. Chemistry A European Journal 2011, 17, 9970. <http://dx.doi.org/10.1002/chem.201101148>
  • Xu Qianying, Liu Zhongfang, Hu Xiaoli, Kong Ling, Liu Shaopu: Interaction of adenine with palladium chloride, determination of adenine via resonance Rayleigh scattering method. Aldrichim Acta 2011, 707, 114. <http://dx.doi.org/10.1016/j.aca.2011.08.051>
  • Fernández-Botello Alfonso, Operschall Bert P., Holy Antonín, Moreno Virtudes, Sigel Helmut: Metal ion-binding properties of 9-[(2-phosphonomethoxy)ethyl]-2-aminopurine (PME2AP), an isomer of the antiviral nucleotide analogue 9-[(2-phosphonomethoxy)ethyl]adenine (PMEA). Steric guiding of metal ion-coordination by the purine-amino group. Dalton Trans 2010, 39, 6344. <http://dx.doi.org/10.1039/c005238h>
  • Janssen Pim G. A., Ruiz-Carretero Amparo, González-Rodríguez David, Meijer E. W., Schenning Albertus P. H. J.: pH-Switchable Helicity of DNA-Templated Assemblies. Angew Chem 2009, 121, 8247. <http://dx.doi.org/10.1002/ange.200903507>
  • Janssen Pim G. A., Ruiz-Carretero Amparo, González-Rodríguez David, Meijer E. W., Schenning Albertus P. H. J.: pH-Switchable Helicity of DNA-Templated Assemblies. Angew Chem Int Ed 2009, 48, 8103. <http://dx.doi.org/10.1002/anie.200903507>
  • Fernández-Botello Alfonso, Holý Antonín, Moreno Virtudes, Operschall Bert P., Sigel Helmut: Intramolecular π–π stacking interactions in aqueous solution in mixed-ligand copper(II) complexes formed by heteroaromatic amines and the nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-aminopurine (PME2AP), an isomer of the antivirally active 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). Inorg Chim Ada 2009, 362, 799. <http://dx.doi.org/10.1016/j.ica.2008.02.035>
  • Lippert Bernhard, Gupta Deepali: Promotion of rare nucleobase tautomers by metal binding. Dalton Trans 2009, 4619. <http://dx.doi.org/10.1039/b823087k>
  • Sigel Helmut, Operschall Bert P., Griesser Rolf: Xanthosine 5′-monophosphate (XMP). Acid–base and metal ion-binding properties of a chameleon-like nucleotide. Chem Soc Rev 2009, 38, 2465. <http://dx.doi.org/10.1039/b902181g>
  • Brasuń Justyna, Matera Agnieszka, Sochacka Elżbieta, Swiatek-Kozlowska Jolanta, Kozlowski Henryk, Operschall Bert P., Sigel Helmut: Acid–base and metal ion binding properties of 2-thiocytidine in aqueous solution. J Biol Inorg Chem 2008, 13, 663. <http://dx.doi.org/10.1007/s00775-008-0351-1>
  • Tharamani Chikka N., Song Haifeng, Ross Andrew R.S., Hughes’ Richard, Kraatz Heinz-Bernhard: Electrochemical investigation of metal ion interactions of a ferrocene deoxyuridine conjugate. Inorg Chim Ada 2008, 361, 393. <http://dx.doi.org/10.1016/j.ica.2007.06.017>
  • Cysewski Piotr: Accurate gas phase acidities of carboxylic acids estimated by scaling the vibrational contribution of ab initio gibbs free energies. J Mol Model 2007, 13, 801. <http://dx.doi.org/10.1007/s00894-007-0200-0>
  • Jang Yun Hee, Hwang Sungu, Chung Doo Soo: DFT Calculation of Site-specific Acid Dissociation Constants of Purine Nucleobases. Chem Lett 2007, 36, 1496. <http://dx.doi.org/10.1246/cl.2007.1496>
  • Sigel Helmut, Massoud Salah S., Song Bin, Griesser Rolf, Knobloch Bernd, Operschall Bert P.: Acid–Base and Metal-Ion-Binding Properties of Xanthosine 5′-Monophosphate (XMP) in Aqueous Solution: Complex Stabilities, Isomeric Equilibria, and Extent of Macrochelation. Chem Eur J 2006, 12, 8106. <http://dx.doi.org/10.1002/chem.200600160>
  • Morell Cerd? Marta, Amantia David, Costisella Burkhard, Houlton Andrew, Lippert Bernhard: Multiple metal binding to 6-oxopurine nucleobases as a source of deprotonation. The role of metal ions at N7 and N3. Dalton Trans 2006, 3894. <http://dx.doi.org/10.1039/b603650c>
  • Sigel Helmut: Acid—Base Properties of Purine Residues and the Effect of Metal Ions: Quantification of Rare Nucleobase Tautomers. ChemInform 2005, 36. <http://dx.doi.org/10.1002/chin.200512300>
  • Sigel Roland K. O.: Group II Intron Ribozymes and Metal Ions - A Delicate Relationship. Eur J Inorg Chem 2005, 2005, 2281. <http://dx.doi.org/10.1002/ejic.200401007>
  • Bianchi Emanuela M., Griesser Rolf, Sigel Helmut: Influence of Decreasing Solvent Polarity (1,4-Dioxane/Water Mixtures) on the Acid-Base and Copper(II)-Binding Properties of Guanosine 5′-Diphosphate. HCA 2005, 88, 406. <http://dx.doi.org/10.1002/hlca.200590026>
  • Sigel Helmut, Griesser Rolf: Nucleoside 5′-triphosphates: self-association, acid–base, and metal ion-binding properties in solution. Chem Soc Rev 2005, 34, 875. <http://dx.doi.org/10.1039/b505986k>
  • Knobloch B., Linert W., Sigel H.: Metal ion-binding properties of (N3)-deprotonated uridine, thymidine, and related pyrimidine nucleosides in aqueous solution. Proceedings of the National Academy of Sciences 2005, 102, 7459. <http://dx.doi.org/10.1073/pnas.0501446102>