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Title: Definitive solution structures for the 6-formylated versions of 1-beta-D-ribofuranosyl-,1-(2’-deoxy beta-D-ribofuranosyl)-, and 1-beta-D-arabinofurano
Authors: Groziak, MP ×
Lin, R
Stevens, WC
Wotring, LL
Balzarini, Jan
Witvrouw, Myriam
De Clercq, Erik #
Issue Date: 1996
Series Title: Nucleosides & Nucleotides vol:15 pages:1041-1057
Abstract: ROESY and NOESY NMR spectroscopic analyses of the ribofuranosyl (la), 2'-deoxyribofuranosyl (Ib), and arabinofuranosyl (Ic) derivatives of 6-formyluracil in (CD3)(2)SO and D2O solutions have established that each exclusive 7,O5'-cyclic hemiacetal diastereomer of la,b and the major 7,O2'-cyclic hemiacetal diastereomer of Ic possess the 7R configuration. In addition, (7R)-1c has been shown to be thermodynamically more stable than (7S)-1c, contrary to our previous indication. A new, higher yielding synthetic route to in has been developed, Ib has been obtained for the first time in crystalline form, the route to Ic has been modified to better accommodate large scale preparations, and a new, fourth member of this class, 6-formylthymidine (Id), has been synthesized and its solution structures in (CD3)(2)SO, D2O, and CD3OD have been determined. Antitumor and antiviral evaluations of la-e have revealed no significant levels of activity.
ISSN: 0732-8311
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
Molecular Virology and Gene Therapy
× corresponding author
# (joint) last author

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