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Identification of Intermediates in the Biosynthesis of PR Toxin by Penicillium roqueforti
Author(s) -
Riclea Ramona,
Dickschat Jeroen S.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201506128
Subject(s) - penicillium roqueforti , toxin , biosynthesis , identification (biology) , penicillium , microbiology and biotechnology , chemistry , biology , computational biology , biochemistry , genetics , enzyme , ecology
Abstract The sesquiterpenoid 7‐ epi ‐neopetasone was synthesized via the Wieland–Miescher ketone. The compound was identical to a previously tentatively identified headspace constituent of Penicillium roqueforti. Feeding experiments with 13 C‐labeled mevalonolactone isotopomers demonstrated that oxidation at C12 and an isomerization of the C11C12 to a C7C11 double bond must occur independently and not via a C7‐C11‐C12 allyl radical in one step. Feeding with (11,12,13‐ 13 C 3 )‐7‐ epi ‐neopetasone resulted in labelling of the PR toxin, thus establishing this compound as a newly identified pathway intermediate.