Description
1-β-D-Arabinofuranosyluracil (ara-U) is an inactive metabolite of cytarabine . Ara-U is formed when cytarabine undergoes deamination by cytidine deaminase.
Chemical Properties
White to Off-White Solid
Uses
1-beta-D-Arabinofuranosyluracil is used for the treatment of severe acute respiratory syndrome (SARS).
Definition
ChEBI: A natural product found in Lepisorus contortus.
Synthesis
A classic synthetic method for 1-beta-D-Arabinofuranosyluracil (arabinoside Ara-U) is a two-step process using uridine as a starting material: First, uridine is heated with diphenyl carbonate in dimethylformamide (DMF) with potassium carbonate or sodium bicarbonate as a catalyst, resulting in dehydration cyclization to generate the key intermediate 2,2'-anhydrouridine. Subsequently, under acidic conditions (e.g., using 2 N HCl), hydrolysis occurs, causing nucleophilic ring-opening of the dehydration bond and introducing a β-hydroxyl group at the C-2' position, ultimately yielding the target product Ara-U.
References
[1] DI LIANG . Simultaneous determination of 1-β-d-Arabinofuranosylcytosine and two metabolites, 1-β-d-Arabinofuranosyluracil and 1-β-d-Arabinofuranosylcytosine triphosphate in leukemic cell by HPLC-MS/MS and the application to cell pharmacokinetics[J]. Journal of Chromatography B, 2014, 962: Pages 14-19. DOI:
10.1016/j.jchromb.2014.05.003[2] YOUCEF MEHELLOU . Phosphoramidates of 2′-β-d-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism[J]. Bioorganic & Medicinal Chemistry, 2010, 18 7: Pages 2439-2446. DOI:
10.1016/j.bmc.2010.02.059.
