An Isotopic Labelling Strategy to Study Cytochrome P450 Oxidations of Terpenes

Jan Rinkel; Martin Litzenburger; Rita Bernhardt; Jeroen S Dickschat

doi:10.1002/cbic.201800215

An Isotopic Labelling Strategy to Study Cytochrome P450 Oxidations of Terpenes

Chembiochem. 2018 Jul 16;19(14):1498-1501. doi: 10.1002/cbic.201800215. Epub 2018 Jun 7.

Authors

Jan Rinkel¹, Martin Litzenburger², Rita Bernhardt², Jeroen S Dickschat¹

Affiliations

¹ Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
² Institute of Biochemistry, Saarland University, Campus, Building B2.2, 66123, Saarbrücken, Germany.

PMID: 29697903
DOI: 10.1002/cbic.201800215

Abstract

The cytochrome P450 monooxygenase CYP267B1 from Sorangium cellulosum was applied for the enzymatic oxidation of the sesquiterpene alcohols T-muurolol and isodauc-8-en-11-ol. Various isotopically labelled geranyl and farnesyl diphosphates were used for product identification from micro-scale reactions, for the determination of the absolute configurations of unknown compounds, to follow the stereochemical course of a cytochrome P450-catalysed hydroxylation step, and to investigate kinetic isotope effects. Overall, this study demonstrates that isotopically labelled terpene precursors are highly useful to follow cytochrome P450 dependent oxidations of terpenes.

Keywords: C−H activation; enzyme catalysis; isotope effects; reaction mechanisms; terpenoids.

Abstract

Grants and funding