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Synthesis of high specific radioactivity 3,5‐[ 3 H 6 ]dimethoxy‐4‐hydroxyacetophenone, an inducing compound of the vir gene in Agrobacterium tumefaciens
Author(s) -
Lee Sungsook,
Morimoto Hiromi,
Williams Philip G.
Publication year - 1997
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(199706)39:6<461::aid-jlcr992>3.0.co;2-k
Subject(s) - agrobacterium tumefaciens , acetosyringone , chemistry , agrobacterium , reagent , stereochemistry , gene , transformation (genetics) , biochemistry , organic chemistry
Acetosyringone (3,5‐dimethoxy‐4‐hydroxyacetophenone, 1 ) is one of the plant signals that induce the vir genes of Agrobacterium tumefaciens which causes crown gall tumours on dicotyledonous plants. Vir gene induction is enhanced by other environmental factors like specific monosaccarides and acidic pH. However, it is still unclear how the inducer interacts with Agrobacterium . To identify the receptor(s) in Agrobacterium tumefaciens to which the plant signal binds, highly radioactive acetosyringone (3,5‐[ 3 H 6 ]dimethoxy‐4‐hydroxyacetophenone 6 ) was synthesized using C 3 H 3 I which was generated by two different methods. In Method 1, C 3 H 3 I was generated from 4‐[methyl‐ 3 H]methoxy biphenyl to give methyl species with tritium NMR peak intensity ratios (C 3 H 3 : C 3 H 2 : C 3 HH 2 = 44 : 42 : 14), and a calculated specific radioactivity of 56.1 Ci/mmole. Method 2 gave higher specific radioactivity reagent (72.6 Ci/mmole), with measured NMR peak intensity ratios of ( 3 H 3 : C 3 H 2 : C 3 HH 2 = 87 : 7 : 6). © John Wiley & Sons, Ltd.