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A flexible synthesis of the four stereoisomeric enantiomerically pure 5 -nor carbocyclic adenosine analogues 4b, ent-4b, 5b and ent-5b starting from the common enantio-merically pure allylic monoacetate 3 has been developed. Each of the nucleoside analogues was transformed into the corresponding 4 -phosphonates and subsequently into the diphosphoryl-phosphonates 4e, ent-4e, 5e, and ent-5e, respectively.
The substrate properties of four carbocyclic d and l nucleoside 5'-triphosphate analogs toward HIV and AMV reverse transcriptases and terminal deoxynucleotidyl transferase were evaluated. The compounds of the d-β and l-β series were found to be terminating substrates for these enzymes, while the derivatives of the d-α and l-α series were recognized only by terminal deoxynucleotidyl transferase, suggesting...
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