Synthesis of tritium- and deuterium-labeled 9-beta-D-arabinofuranosyladenine and the tritium-labeled 5'-monophosphate ester with increased metabolic stability.
Preparation of both a 5'-deuterium and a 5'-tritium-labeled 9-beta-D-arabinofuranosyladenine (6a and 6b) by reduction of the protected 5'-aldehyde 4 is described. Conversion of 6b to the 5'-tritium-labeled 5'-monophosphate 7b was effected directly with a phosphoryl chloride-formic acid reagent. The product 7b exhibited consistently higher blood levels of nonvolatile tritium than the 2-labeled compound when tested in dogs.
D000227:Adenine Nucleotides / Q000097:blood / Q000138:chemical synthesis*; D000818:Animals; D003903:Deuterium; D004285:Dogs; D007553:Isotope Labeling / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D013056:Spectrophotometry, Ultraviolet; D014316:Tritium; D014740:Vidarabine / Q000097:blood / Q000138:chemical synthesis*
D000227:Adenine Nucleotides; D011684:Purine Nucleosides; D014316:Tritium; D003903:Deuterium; D014740:Vidarabine