Selective oxidation of carotenoid-derived aroma compounds by CYP260B1 and CYP267B1 from Sorangium cellulosum So ce56

Applied Microbiology and Biotechnology
Martin Litzenburger, Rita Bernhardt

Abstract

Due to their bioactive properties as well as their application as precursors in chemical synthesis, hydroxylated isoprenoids and norisoprenoids are very valuable compounds. The efficient hydroxylation of such compounds remains a challenge in organic chemistry caused by the formation of a variety of side products and lack of overall regio- and stereoselectivity. In contrast, cytochromes P450 are known for their selective oxidation under mild conditions. Here, we demonstrate for the first time the ability of myxobacterial CYP260B1 and CYP267B1 from Sorangium cellulosum So ce56 to oxidize such carotenoid-derived aroma compounds. A focused library of 14 substrates such as ionones, damascones, as well as some of their isomers and derivatives was screened in vitro. Both P450s were capable of an efficient oxidation of all tested compounds. CYP260B1-dependent conversions mainly formed multiple products, whereas conversions by CYP267B1 resulted predominantly in a single product. To identify the main products by NMR spectroscopy, an Escherichia coli-based whole-cell system was used. CYP267B1 showed a hydroxylase activity towards the formation of allylic alcohols. Likewise, CYP260B1 performed the allylic hydroxylation of β-damascone [(E)-...Continue Reading

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Citations

Mar 8, 2016·Organic & Biomolecular Chemistry·Alexander SchifrinRita Bernhardt
May 15, 2016·FEBS Letters·Sandra Giovanna Salamanca-PinzonRita Bernhardt
Oct 12, 2017·Applied Microbiology and Biotechnology·Natalia PutkaradzeRita Bernhardt
Apr 27, 2018·Chembiochem : a European Journal of Chemical Biology·Jan RinkelJeroen Sidney Dickschat
Nov 30, 2018·Chembiochem : a European Journal of Chemical Biology·Yujie YuanTiangang Liu
Apr 25, 2017·Journal of Dairy Science·E B YehM A Drake
Dec 24, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Stefano Serra, Davide De Simeis
Jul 23, 2018·Applied Microbiology and Biotechnology·Maciej SzaleniecMarina Donova

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