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Pure Appl. Chem., 1999, Vol. 71, No. 9, pp. 1727-1740

http://dx.doi.org/10.1351/pac199971091727

Metal ion-binding properties of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). Why is its diphosphorylated form, PMEApp4-, initially a better substrate for nucleic acid polymerases than (2'-deoxy)-adenosine 5'-triphosphate (dATP4-/ATP4-)?

H. Sigel

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  • Sigel Astrid, Operschall Bert P., Sigel Helmut: Comparison of the π-stacking properties of purine versus pyrimidine residues. Some generalizations regarding selectivity. J Biol Inorg Chem 2014. <http://dx.doi.org/10.1007/s00775-013-1082-5>
  • Gómez-Coca Raquel B., Sigel Astrid, Operschall Bert P., Holy Antonín, Sigel Helmut: Solution properties of metal ion complexes formed with the antiviral and cytostatic nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]-2-amino-6-dimethylaminopurine (PME2A6DMAP). Can. J. Chem. 2014, 140320143742009. <http://dx.doi.org/10.1139/cjc-2014-0041>
  • 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>
  • Evans Bradley S., Zhao Changming, Gao Jiangtao, Evans Courtney M., Ju Kou-San, Doroghazi James R., van der Donk Wilfred A., Kelleher Neil L., Metcalf William W.: Discovery of the Antibiotic Phosacetamycin via a New Mass Spectrometry-Based Method for Phosphonic Acid Detection. ACS Chem. Biol. 2013, 8, 908. <http://dx.doi.org/10.1021/cb400102t>
  • 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>
  • Al-Sogair Fawzia M., Operschall Bert P., Sigel Astrid, Sigel Helmut, Schnabl Joachim, Sigel Roland K. O.: Probing the Metal-Ion-Binding Strength of the Hydroxyl Group. Chemistry Review 2011, 111, 4964. <http://dx.doi.org/10.1021/cr100415s>
  • 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>
  • 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>
  • Grigoriev F. V., Golovacheva A. Yu., Romanov A. N., Kondakova O. A., Sulimov V. B.: The thermodynamic characteristics of formation of organic molecule complexes with the magnesium ion in water: The results of quantum-chemical modeling. Russ J Phys Chem 2009, 83, 565. <http://dx.doi.org/10.1134/S0036024409040098>
  • Freisinger Eva, Griesser Rolf, Lippert Bernhard, Moreno-Luque Cristóbal F., Niclós-Gutiérrez Juan, Ochocki Justyn, Operschall Bert P., Sigel Helmut: Comparison of the Surprising Metal-Ion-Binding Properties of 5- and 6-Uracilmethylphosphonate (5Umpa2− and 6Umpa2−) in Aqueous Solution and Crystal Structures of the Dimethyl and Di(isopropyl) Esters of H2(6Umpa). Chem Eur J 2008, 14, 10036. <http://dx.doi.org/10.1002/chem.200800998>
  • 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>
  • 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>
  • Gómez-Coca Raquel B., Kapinos Larisa E., Holý Antonín, Vilaplana Rosario A., González-Vílchez Francisco, Sigel Helmut: Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). J Biol Inorg Chem 2004, 9, 961. <http://dx.doi.org/10.1007/s00775-004-0591-7>
  • Da Costa Carla P., Okruszek Andrzej, Sigel Helmut: Complex Formation of Divalent Metal Ions with Uridine 5′-O-Thiomonophosphate or Methyl Thiophosphate: Comparison of Complex Stabilities with Those of the Parent Phosphate Ligands. Chem Eur J of Chem Bio 2003, 4, 593. <http://dx.doi.org/10.1002/cbic.200200551>
  • Fernández-Botello Alfonso, Holý Antonı́n, Moreno Virtudes, Sigel Helmut: Stability and structure of binary and ternary metal ion complexes in aqueous solution of the quaternary 1-[2-(phosphonomethoxy)ethyl] derivative of 2,4-diaminopyrimidine (PMEDAPy−). Properties of an acyclic nucleotide analogue. J Polyhedron 2003, 22, 1067. <http://dx.doi.org/10.1016/S0277-5387(03)00093-7>
  • Fernández-Botello Alfonso, Gómez-Coca Raquel B., Holý Antonı́n, Moreno Virtudes, Sigel Helmut: Metal-ion binding properties of O-phosphonatomethylcholine (PMCh−). Inorg Chim Ada 2002, 331, 109. <http://dx.doi.org/10.1016/S0020-1693(01)00763-0>
  • Kampf Gunnar, Lüth Marc Sven, Kapinos Larisa E., Müller Jens, Holý Antonín, Lippert Bernhard, Sigel Helmut: Formation of Ternary Complexes by Coordination of (Diethylenetriamine)Platinum(II) to N1 or N7 of the Adenine Moiety of the Antiviral Nucleotide Analogue 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA): Comparison of the Acid-Base and Metal-Ion-Binding Properties of PMEA, (Dien)Pt(PMEA-N1), and (Dien)Pt(PMEA-N7). Chem Eur J 2001, 7, 1899. <http://dx.doi.org/10.1002/1521-3765(20010504)7:9<1899::AID-CHEM1899>3.0.CO;2-5>
  • Sigel Helmut, Bianchi Emanuela M., Corfù Nicolas A., Kinjo Yoshiaki, Tribolet Roger, Martin R. Bruce: Stabilities and Isomeric Equilibria in Solutions of Monomeric Metal-Ion Complexes of Guanosine 5′-Triphosphate (GTP4−) and Inosine 5′-Triphosphate (ITP4−) in Comparison with Those of Adenosine 5′-Triphosphate (ATP4−). Chem Eur J 2001, 7, 3729. <http://dx.doi.org/10.1002/1521-3765(20010903)7:17<3729::AID-CHEM3729>3.0.CO;2-E>