The biosynthesis of cochlioquinones (1) and (2) was studied by isotopic tracer experiments with 13C- and 14C-labelled compounds. The sequence of intermediates involved in the biosynthesis of the acetogenin moiety of (1) and (2) was assessed by incorporation of 14C-labelled precursors. The use of doubly-labelled 13C-acetate and 13C n.m.r. spectroscopy made it possible to determine the rest of the pathway as follows: prenylation of the acetogenin-derived aromatic nucleus, decarboxylation and hydroxylation in the same position, and finally cyclization of the terpenoid moiety. Details of the cyclization process were obtained by the use of 18O2 and mass spectrometry.
Biosynthesis of cochlioquinones / L. Canonica, M.G. Beretta, L. Colombo, C.M.A. Gennari, B.M. Ranzi, C. Scolastico. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - (1980), pp. 2686-2690. [10.1039/P19800002686]
Biosynthesis of cochlioquinones
C.M.A. Gennari;C. Scolastico
1980
Abstract
The biosynthesis of cochlioquinones (1) and (2) was studied by isotopic tracer experiments with 13C- and 14C-labelled compounds. The sequence of intermediates involved in the biosynthesis of the acetogenin moiety of (1) and (2) was assessed by incorporation of 14C-labelled precursors. The use of doubly-labelled 13C-acetate and 13C n.m.r. spectroscopy made it possible to determine the rest of the pathway as follows: prenylation of the acetogenin-derived aromatic nucleus, decarboxylation and hydroxylation in the same position, and finally cyclization of the terpenoid moiety. Details of the cyclization process were obtained by the use of 18O2 and mass spectrometry.
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