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Original Articles

O2,1-Anhydro-(β -D-Psicofuranosyl)Thymine and 1-(1,4-O-Anhydro-β -D-Psicofuranosyl)Thymine: The Crystal Structures Versus the 1H NMR and AB Initio Data

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Pages 1015-1019 | Published online: 10 Dec 2007

REFERENCES

  • Roivainen , J. , Vepsäläinen , J. , Azhayev , A. and Mikhailopulo , I. A. 2002 . Synthesis of anhydro psicofuranosyl nucleosides . Tetrahedron Lett. , 43 : 6553 – 6555 .
  • Kulak , T. I. , Tkachenko , O. V. , Sentjureva , S. L. , Vepsäläinen , J. and Mikhailopulo , I. A. 2005 . Synthesis of pyrimidine 1′,3′-anhydro-β -D-psico- and -sorbo-furanosyl nucleosides . Synlett , : 1683 – 1686 .
  • Miles , D. W. , Robins , M. J. , Robins , R. K. , Winkley , M. W. and Eyring , H. 1969 . Circular dichroism of nucleoside derivatives. IV. Uracil derivatives . J. Am. Chem. Soc. , 91 : 824 – 831 .
  • Yoshimura , Y. , Ueda , T. and Matsuda , A. 1991 . Synthesis of 6,1′-propanouridine, fixed in syn-conformation by a spiro-carbon bridge . Tetrahedron Lett. , 32 : 4549 – 4552 .
  • Hrebabecky , H. and Farkas , J. 1974 . Nucleic acid components and their analogs. CLXV. Synthesis of 1-β -D-psicofuranosyluracil and 1-β -D-psicofuranosylcytosine . Coll. Czech. Chem. Commun. , 39 : 1098 – 1106 .
  • Pradeepkumar , P. I. , Cheruku , P. , Plashkevych, Acharya , P. , Gohil , S. and Chattopadhyaya , J. 2004 . Synthesis, physicochemical and biochemical studies of 1′,2′-oxetane constrained adenosine and guanosine modified oligonucleotides, and their comparison with those of the corresponding cytidine and thymidine analogues . J. Am. Chem. Soc. , 126 : 11484 – 11499 .
  • Bogucka , M. , Naus , P. , Pathmasiri , W. , Barman , J. and Chattopadhyaya , J. 2005 . Facile preparation of the oxetane-nucleosides . Org. Biomol. Chem. , 3 : 4362 – 4372 .
  • www.ccdc.cam.ac.uk/data_request/cifCCDC 635624 and 635625 contain the supplementary crystallographic data for these structures. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at
  • van Wijk , J. , Haasnot , C. A.G. , de Leeuw , F. A.A.M. , Huckriede , B. D. , Westra Hoekzema , A. J.A. and Altona , C. 1999 . PSEUROT 6.3. A program for the conformational analysis of five-membered rings , Leiden , , the Netherlands : Leiden Institute of Chemistry .
  • de Leeuw , F. A.A.M. and Altona , C . 1982 . Conformational analysis of β -D-ribo-, β -D-deoxyribo-, β -D-arabino-, β -D-xylo- and β -D-lyxo-nucleosides from proton-proton coupling constants . J. Chem. Soc. Perkin II , : 375 – 384 .
  • We have recently published the crystal structure of 9-(1′,3′-O-anhydro-β -D-psicofuranosyl)adenine,[11] the furanosyl ring of which adopts an N-type sugar pucker with the following pseudorotational parameters: P N = 50.2° and νmax = 34.9°. These data are in harmony with the average corresponding values, 39.80° and 35.07°, for the same nucleoside resulted from the ab initio calculations utilizing 6-31G* Hartree-Fock geometry optimization.[6]
  • Roivainen , J. , Mikhailopulo , I. A. , Reuter , H. and Eickmeier , H. 2006 . 1-(1,3-Anhydro-β -D-psicofuranosyl)adenine . Acta Cryst. , C62 : o659 – o660 .
  • Booth , H. 1965 . The variation of vicinal proton-proton coupling constants with orientation of electronegative substituents . Tetrahedron Lett. , 6 : 411 – 416 .
  • Jaworski , A. , Ekiel , I. and Shugar , D. 1978 . Coupling constants between cisoidal protons in pentose nucleosides. Limitations of range application of Karplus relation, and solution conformations of β -arabinofuranosyl and β -xylofuranosyl nucleosides . J. Am. Chem. Soc. , 100 : 4357 – 4361 .

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