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Sphinganine‐Like Biogenesis of ( E )‐1‐Nitropentadec‐1‐ene in Termite Soldiers of the Genus Prorhinotermes
Author(s) -
Jirošová Anna,
Majer Pavel,
Jančařík Andrej,
Dolejšová Klára,
Tykva Richard,
Šobotník Jan,
Jiroš Pavel,
Hanus Robert
Publication year - 2014
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201300665
Subject(s) - ene reaction , biogenesis , biosynthesis , glycine , stereochemistry , serine , genus , amino acid , chemistry , biology , biochemistry , botany , enzyme , gene
In 1974, ( E )‐1‐nitropentadec‐1‐ene, a strong lipophilic contact poison of soldiers of the termite genus Prorhinotermes , was the first‐described insect‐produced nitro compound. However, its biosynthesis remained unknown. In the present study, we tested the hypothesis that ( E )‐1‐nitropentadec‐1‐ene biosynthesis originates with condensation of amino acids with tetradecanoic acid. By using in vivo experiments with radiolabeled and deuterium‐labeled putative precursors, we show that ( E )‐1‐nitropentadec‐1‐ene is synthesized by the soldiers from glycine or L ‐serine and tetradecanoic acid. We propose and discuss three possible biosynthetic pathways.