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-...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1975-10, Vol.18 (10), p.1041-1044
Main Authors: Baker, David C, Haskell, Theodore H
Format: Article
Language:English
Subjects:
Adenine Nucleotides - blood
Adenine Nucleotides - chemical synthesis
Animals
Deuterium
Dogs
Isotope Labeling - methods
Magnetic Resonance Spectroscopy
Purine Nucleosides - chemical synthesis
Spectrophotometry, Ultraviolet
Tritium
Vidarabine - blood
Vidarabine - chemical synthesis
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00244a022