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9-β-D-Arabinofuranosyladenine (AraA)

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Part of the book series: Antibiotics ((1512,volume 5 / 2))

Abstract

AraA (9-β-D-arabinofuranosyladenine; vidarabine; NSC-404241) was first synthesized as a potential antitumor agent in 1960 (Lee et al.) and later isolated by Parke, Davis and Company (British Patent No. 1,159,290) as an antibiotic produced by Streptomyces antibioticus. Chemical synthesis, initially achieved through the conversion of a xylonucleoside to araA (Lee et al., 1960; Reist et al., 1962), was subsequently accomplished on a larger scale by the condensation of 2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride with N-benzoyladenine (Glaudemans and Fletcher, 1963; Reist et al., 1964). Detailed discussions of the synthetic procedures and chemical properties of araA and certain other D-arabinosyl nucleosides may be found in the comprehensive reviews by Cohen (1966) and Suhadolnik (1970).

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Cass, C.E. (1979). 9-β-D-Arabinofuranosyladenine (AraA). In: Hahn, F.E. (eds) Mechanism of Action of Antieukaryotic and Antiviral Compounds. Antibiotics, vol 5 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46407-2_3

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