N6-alkyladenosines and adenines labelled with tritium

Article abstract of DOI:10.1002/(SICI)1099-1344(200004)43:5<523::AID-JLCR339>3.0.CO;2-O

Catalytic dehalogenation of 2-chloroadenosine with tritium gas led to tritium labelled adenosine which was subsequently alkylated with (E)-4-t-butoxy-3-methylbut-2-enyl bromide or with 3-methylbut-2-enyl bromide to yield labelled (E)-N⁶-(4-t-butoxy-3-methylbut-2-enyl)adenosine (2a) and N⁶-(3-methylbut-2-enyl)adenosine (2b). Acidic hydrolysis of 2b gave N6-(3-methylbut-2-enyl)adenine while acidolysis of a with trifluoroacetic acid led to a mixture of (E)-zeatin riboside and (E)-zeatin. Hydrogenation of (Z/E)-zeatin riboside (³H₂, PdO/BaSO₄) afforded labelled dihydrozeatin riboside and, after hydrolysis, dihydrozeatin.