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Method for synthesis of 2‐azido‐N(6)‐m‐tritiobenzylaminopurine, a photoaffinity label for cytokinin‐binding proteins in plants
Author(s) -
Cooper Geoffrey,
Bourell James,
Kaminek Miroslav,
Fox J. Eugene
Publication year - 1988
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/jlcr.2580250906
Subject(s) - chemistry , cytokinin , photoaffinity labeling , yield (engineering) , combinatorial chemistry , tritium , pyridine , plant hormone , chemical synthesis , peptide , tritium illumination , stereochemistry , binding site , organic chemistry , biochemistry , in vitro , auxin , materials science , physics , nuclear physics , metallurgy , gene
A method for tritiation of 2‐azido‐N(6)‐benzyladenine (AZBA), a photoaffinity analog of the plant hormone N(6)‐benzyladenine (BA), was developed. The synthetic sequence involves condensation of 2,6‐dichloropurine with m‐iodobenzylamine to yield 2‐chloro‐N(6)‐m‐iodobenzyladenine, followed by selective hydrodeiodination with tritium gas over palladium catalyst in pyridine solution to give 2‐chloro‐N(6)‐m‐tritiobenzyladenine. The known conversion of this compound to AZBA enables preparation of the photoaffinity label compound with specific activity high enough to permit detection of cytokinin‐binding proteins existing at low concentrations in plant tissues.