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Ara-Nucleotides feature an opposite stereochemistry at the 2' carbon atom compared to ribo-nucleotides. They are incorporated into DNA by polymerases however, the DNA strand is only poorly elongated from the 3' ara-nucleotide residue and thus provides an opportunity for exonucleases to remove the ara-nucleotide.

Cytarabine (Cytosine arabinoside, ara-C) is a commonly used chemotherapy agent used mainly in the treatment of leukemia and non-Hodgkin lymphoma. It been shown to be misincorporated into DNA double helix, which has significant conformational consequences that affect the function of DNA.

Vidarabine (Adenosine arabinoside, ara-A) is an anti-viral drug which is active against herpes simplex and varicella zoster viruses.

Fludarabine (F-ara-A) is an antineoplastic agent which causes inhibition of DNA synthesis by inhibiting ribonucleotide reductase and DNA polymerase.[1]

Selected References

[1] Young et al. (1995) Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc., p. 90.