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An Isotopic Labelling Strategy to Study Cytochrome P450 Oxidations of Terpenes
Author(s) -
Rinkel Jan,
Litzenburger Martin,
Bernhardt Rita,
Dickschat Jeroen S.
Publication year - 2018
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.201800215
Subject(s) - terpene , hydroxylation , chemistry , monooxygenase , cytochrome p450 , sesquiterpene , cytochrome , labelling , stereochemistry , isotopic labeling , organic chemistry , enzyme , biochemistry
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.