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Synthesis 1990; 1990(10): 962-966
DOI: 10.1055/s-1990-27066
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Dideoxygenated Purine Nucleosides Substituted at the 8-Position: Chemical Synthesis and Stability

Greg S. Buenger* , Vasu Nair
  • *Department of Chemistry, The University of Iowa, Iowa City. IA 52242, USA
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Publikationsdatum:
17. September 2002 (online)

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Synthesis of novel analogues of the largely unknown family of 8-substituted 2′,3′-dideoxyadenosines is described. Hydrolytic deamination of two of these analogues by mammalian adenosine deaminase was utilized for an enzymatic synthesis of 2′,3′- dideoxyinosine compounds. The glycosidic bond of 2′,3′-dideoxy-8- hydtoxyadenosine is remarkably stable with respect to hydrolytic cleavage which is very unusual for a dideoxynucleoside.