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N 6 ‐alkyladenosines and adenines labelled with tritium
Author(s) -
Hanuš Jan,
Siglerová Věra,
Matucha Miroslav
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(200004)43:5<523::aid-jlcr339>3.0.co;2-o
Subject(s) - chemistry , riboside , hydrolysis , tritium , bromide , adenosine , trifluoroacetic acid , yield (engineering) , medicinal chemistry , organic chemistry , biochemistry , physics , materials science , nuclear physics , metallurgy
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 )‐N 6 ‐(4‐ t ‐butoxy‐3‐methylbut‐2‐enyl)adenosine ( 2a ) and N 6 ‐(3‐methylbut‐2‐enyl)adenosine ( 2b ). Acidic hydrolysis of 2b gave N 6 ‐(3‐methylbut‐2‐enyl)adenine while acidolysis of 2a with trifluoroacetic acid led to a mixture of ( E )‐zeatin riboside and ( E )‐zeatin. Hydrogenation of ( Z / E )‐zeatin riboside ( 3 H 2 , PdO/BaSO 4 ) afforded labelled dihydrozeatin riboside and, after hydrolysis, dihydrozeatin. Copyright © 2000 John Wiley & Sons, Ltd.