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Synthesis of N‐[3‐OXO‐(4,5‐ 3 H 2 )‐hexanoyl] homoserine lactone: Biologically active tritium‐labelled vibrio fischeri autinducer
Author(s) -
Kaplan H. B.,
Eberhard A.,
Widrig C.,
Greenberg E. P.
Publication year - 1985
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.2580220411
Subject(s) - chemistry , lactone , tritium , homoserine , biological activity , tritium illumination , vibrio , chemical synthesis , stereochemistry , catalysis , quorum sensing , organic chemistry , bacteria , biochemistry , physics , genetics , virulence , biology , nuclear physics , in vitro , gene
N‐(3‐oxo‐4‐hexenoyl) homoserine lactone was synthesized and then reduced with Wilkinson's catalyst in the presence of tritium gas to form N‐[3‐oxo‐(4,5‐ 3 H 2 )‐hexanoyl] homoserine locatone (45–55 Ci/mmol). The labelled compound was indistinguishable from the autoinducer for Vibrio fischeri luciferase [N‐(3‐oxohexanoyl) homosernine lactone] by high‐performance liquid chromatography and it was biologically active.