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Keywords:

  • Nucleosides;
  • Nucleotides

Abstract

The nucleosides participating in biological processes consist of a sugar and a heterocyclic nucleobase; the nucleotides, which occur as monomers and as building units of polymeric nucleic acids, contain an additional phosphoester group. The complexity of the molecules leads to a complex stereochemistry with which the present progress report is concerned. Particular attention will be devoted to conformational considerations at the sugar groups, the syn-anti conformation, the position of the C(5′)[BOND]O(5′) bond relative to the sugar group, and the conformation of the phosphoester bonds. The article touches upon base pairing and base stacking, as well as forces stabilizing the syn conformation, and also deals with the reaction mechanism of the enzyme pancreatic ribonuclease as established from the stereochemistry of nucleotides and the mechanisms of action of the antileukemia drug 6-azauridine and the antibiotic actinomycin D. Views on the effects of the unusual structures of the “rare” nucleosides 4-thiouridine, isopentenyladenosine, and dihydrouridine on the structure of transfer ribonucleic acid are also presented.