Structural Properties of the Neutral and Monoanionic Forms of Xanthosine, Highly Relevant to Their Substrate Properties with Various Enzyme Systems

References

• Kim , J.H. , Ryan , M.G. , Knaut , H. and Hille , R. 1996 . The reductive half-reaction of xanthine oxidase. The involvement of prototropic equilibria in the course of the catalytic sequence . J. Biol. Chem. , 271 : 6771 – 6780 .
   PubMed Web of Science ®Google Scholar
• Sau , A.K. , Mondal , M.S. and Mitra , S. 2000 . Effects of pH and temperature on the reaction of milk Xanthine oxidase with 1-methylxanthine . J. Chem. Soc. Dalton Trans. , 20 : 3688 – 3692 .
   Google Scholar
• Cavalieri , L. , Fox , J. , Stone , A. and Chang , N. 1954 . On the nature of xanthine and substituted xanthines in solution . J. Am. Chem. Soc. , 76 : 1119 – 1122 .
   Web of Science ®Google Scholar
• Roy , K.B. and Miles , H.T. 1983 . Tautomerism and ionization of xanthosine . Nucleosides and Nucleotides , 2 : 231 – 242 .
   Web of Science ®Google Scholar
• Stoychev , G. , Kierdaszuk , B. and Shugar , D. 2002 . Xanthosine and xanthine: Substrate properties with purine nucleoside phosphorylases, and relevance to other enzyme systems . Eur. J. Biochem. , 269 : 4048 – 4057 .
   PubMedGoogle Scholar
• Cobas , C. , Cruces , J. and Sardina , F.J. MestRe-C 2.3a, Magnetic Resonance Companion NMR Data Processing Program. Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 1706 Santiago de Compostela Spain
   Google Scholar
• Delaglio , F. , Grzesiek , S. , Vuister , G.W. , Zhu , G. , Pfeifer , J. and Bax , A. 1995 . NMRPipe: A multidimensional spectral processing system based on UNIX pipes . J. Biomol. NMR. , 6 : 277 – 293 .
   PubMed Web of Science ®Google Scholar
• Bartels , C. , Xia , T.-E. , Billeter , M. , Guntert , P. and Wüthrich , K. 1995 . The Program XEASY for the computer-supported NMR spectral analysis of biological macromolecules . J. Biol. NMR , 5 : 1 – 10 .
   PubMed Web of Science ®Google Scholar
• Bodenhausen , G. and Roben , D.J. 1980 . Natural abundance Nitrogen-15 NMR by enchanced heteronuclear spectroscopy . Chem. Phys. Lett. , 69 : 185 – 189 .
   Web of Science ®Google Scholar
• Hurd , R.E. 1990 . Gradient-enhanced spectroscopy . J. Magn. Reson. , 87 : 422 – 428 .
   Web of Science ®Google Scholar
• Bothner-By , A. , Lee Stephens , J. , Warren , C. and Jeanloz , R. 1984 . Structure determination of a tetrasaccharide: Transient nuclear overhauser effects in the rotating frame . J. Am. Chem. Soc. , 106 : 811 – 813 .
   Web of Science ®Google Scholar
• Poznański , J. Iterative Seven Spin System Simulation, Program made within the Biosym research fellowship on a field of NMR software
   Google Scholar
• Gunther , H. 1980 . NMR Spectroscopy Chichester : John Wiley and Sons .
   Google Scholar
• de Leeuw , H.P.M. , Haasnoot , C.A.G. and Altona , C. 1980 . Empirical correlations between conformational parameters in β-D-furanoside fragments derived from a statistical survey of crystal structures of nucleic acid constituents . Israel J. Chem. , 20 : 108 – 126 .
   Web of Science ®Google Scholar
• Clark , M. , Cramer , R.D. III and Van Opdenbosh , N. 1989 . Validation of the general purpose tripos 5.2 Force Field . J. Comput. Chem. , 10 : 982 – 1012 .
   Web of Science ®Google Scholar
• Weiner , J.S. , Kollman , P.A. , Case , D.A. , Singh , U.C. , Ghio , C. , Alagona , G. , Profeta , S. and Weiner , P. 1984 . A new force field for molecular mechanical simulation of nucleic acids and proteins . J. Am. Chem. Soc. , 106 : 765 – 784 .
   Web of Science ®Google Scholar
• Schmidt , M.W. , Baldridge , K.K. , Boatz , J.A. , Elbert , S.T. , Gordon , M.S. , Jensen , J.J. , Koseki , S. , Matsunaga , N. , Nguyen , K.A. , Su , S. , Windus , T.L. , Dupuis , M. and Montgomery , J.A. 1993 . General atomic and molecular electronic structure system . J. Comput. Chem. , 14 : 1347 – 1363 .
   Web of Science ®Google Scholar
• Francl , M.M. , Pietro , W.J. , Hehre , W.J. , Binkley , J.S. , Gordon , M.S. , DeFrees , D.J. and Pople , J.A. 1982 . Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements . J. Chem. Phys. , 77 : 3654 – 3665 .
   Web of Science ®Google Scholar
• Hertwig , R.H. and Koch , W. 1997 . On the parameterization of the local correlation functional. What is Becke-3-LYP? . Chem. Phys. Lett. , 268 : 345 – 351 .
   Web of Science ®Google Scholar
• Cammi , R. and Tomasi , J. 1995 . Remarks on the use of the apparent surface charges (ASC) methods in solvation problems: iterative versus matrix-inversion procedures and the renormalization of the apparent charges . J. Comput. Chem. , 16 : 1449 – 1458 .
   Web of Science ®Google Scholar
• Langlet , J. , Claverie , P. , Caillet , J. and Pullman , A. 1988 . Improvements of the continuum model. 1. Application to the calculation of the vaporization thermodynamic quantities of nonassociated liquids . J. Phys. Chem. , 92 : 1617 – 1631 .
   Web of Science ®Google Scholar
• Amovilli , C. and Mennucci , B. 1997 . Self-consistent-field calculation of Pauli repulsion and dispersion contributions to the solvation free energy in the polarizable continuum model . J. Phys. Chem. B , 101 : 1051 – 1057 .
   Web of Science ®Google Scholar
• Stolarski , R. , Hagberg , C.E. and Shugar , D. 1984 . Studies on the dynamic syn-anti equilibrium in purine nucleosides and nucleotides with the aid of 1H and 13C NMR spectroscopy . Eur. J. Biochem. , 138 : 187 – 192 .
   PubMedGoogle Scholar
• Lesyng , B. , Marck , C. and Seanger , W. 1983 . The crystal structure of anhydrous xanthosine displays intramolecular O(2′)-H … O(3′) hydrogen bond . Z. Naturforsch. , 39 : 720 – 724 .
   Google Scholar
• Civcir , P.U. 2001 . Tautomerism of 6-thioxanthine in gas and aqueous phases using AM1 and PM3 methods . J. Chem. Phys. , 114 : 1582 – 1588 .
   Web of Science ®Google Scholar
• Franchetti , P. and Grifantini , M. 1999 . Nucleoside and non-nucleoside IMP dehydrogenase inhibitors as antitumor and antiviral agents . Curr. Med. Chem. , 6 : 599 – 614 .
   PubMed Web of Science ®Google Scholar
• Bezirjian , Kh.O. , Kocharian , Sh.M. and Akopyan , Zh.I. 1986 . Isolation of a hexameric form of purine nucleoside phosphorylase II from E. coli, Comparative study of trimeric and hexameric forms of the enzyme . Biokhimia , 51 : 1085 – 1092 .
   PubMedGoogle Scholar
• Ashihara , H. and Crozier , A. 1999 . Biosynthesis and catabolism of caffeine in low- caffeine-containing species of Coffea . J. Agricult. Food Chem. , 47 : 3425 – 3431 .
   PubMed Web of Science ®Google Scholar
• Chung , J.H. , Back , J.H. , Park , Y.I. and Han , Y.S. 2001 . Biochemical characterization of a novel hypoxanthine/xanthine dNTP pyrophosphatase from Methanococcus jannaschii . Nucleic Acids Res. , 29 : 3099 – 3107 .
   PubMed Web of Science ®Google Scholar
• Chappe , V. , Mettey , Y. , Vierfond , J.M. , Hanrahan , J.W. , Gola , M. , Verrier , R. and Becq , F. 1998 . Structural basis for specificity and potency of xanthine derivatives as activators of the CFTR chloride channel . British J. Pharmacol. , 123 : 683 – 693 .
   PubMed Web of Science ®Google Scholar
• Vos , S. , Parry , R.J. , Burns , M.R. , de Jersey , J. and Martin , J.L. 1998 . Structures of free and complexed forms of Escherichia coli xanthine-guanine phosphoribosyltransferase . J. Molec. Biol. , 282 : 875 – 889 .
   PubMed Web of Science ®Google Scholar
• Shivashankar , K. , Sujay Subbayya , I.N. and Balaram , H. 2001 . Development of a bacterial screen for novel Hx-Gua PRTase substrates . J. Mol. Microb. Biotechol. , 3 : 557 – 562 .
   PubMed Web of Science ®Google Scholar
• Vos , S. , de Jersey , J. and Martin , J.L. 1997 . Crystal structure of Escherichia coli xanthine phosphoribosyltransferase . Biochemistry , 36 : 4125 – 4134 .
   PubMed Web of Science ®Google Scholar
• Craig , S.P. 3rd and Eakin , A.E. 2000 . Purine phosphoribosyltransferases . J. Biol. Chem. , 275 : 20,231 – 20,234 .
   Web of Science ®Google Scholar
• Jardim , A. , Bergeson , S.E. , Shih , S. , Carter , N. , Lucas , R.W. , Merlin , G. , Myler , P.J. , Stuart , K. and Ullman , B. 1999 . Xanthine phosphoribosyltransferase from Leishmania donovani. Molecular cloning, biochemical characterization, and genetic analysis . J. Biol. Chem. , 274 : 34,403 – 34,410 .
   Web of Science ®Google Scholar
• Mizuno , H. , Fujiwara , T. and Tomita , K. 1969 . The crystal and molecular structure of the sodium salt of xanthine . Bull. Chem. Soc. Japan , 42 : 3099 – 3105 .
   Web of Science ®Google Scholar
• Fikus , M. and Shugar , D. 1969 . Properties of poly-xanthylic acid and its reactions with potentially complementary homopolynucleotides . Acta Biochim. Polon. , 16 : 55 – 84 .
   PubMed Web of Science ®Google Scholar
• Roy , K.B. , Frazier , J. and Miles , H.T. 1979 . Polixanthylic acid: Structures of the ordered forms . Biopolymers , 18 : 3077 – 3087 .
   Web of Science ®Google Scholar
• Arnott , S. , Chandrasekaran , R. , Day , A.W. , Puigjaner , L.C. and Watts , L. 1981 . Double-helical structures for polyxanthylic acid . J. Mol. Biol. , 149 : 489 – 505 .
   PubMed Web of Science ®Google Scholar
• Twanmoh , L.M. , Wood , H.B. Jr. and Driscoll , J.S. 1973 . NMR spectral characteristics of N-H protons in purine derivatives . J. Heterocycl. Chem. , 10 : 187 – 190 .
   Web of Science ®Google Scholar
• Yamamoto , O. , Someno , K. , Wasada , N. , Hiraishi , J. , Hayamizu , K. , Tanabe , K. , Tamura , T. and Yanagisawa , M. 1988 . An integrated spectral data base system including IR, MS, 1H-NMR, 13C-NMR, ESR and Raman spectra . Anal. Sci. , 4 : 233
   Web of Science ®Google Scholar