| Title: | Regioselective hydroxylation of norisoprenoids by CYP109D1 from Sorangium cellulosum So ce56 |
| Author(s): | Khatri Y; Girhard M; Romankiewicz A; Ringle M; Hannemann F; Urlacher VB; Hutter MC; Bernhardt R; |
| Address: | "Department of Biochemistry, Saarland University, Saarbrucken, Germany" |
| Journal Title: | Appl Microbiol Biotechnol |
| DOI: | 10.1007/s00253-010-2756-3 |
| ISSN/ISBN: | 1432-0614 (Electronic) 0175-7598 (Linking) |
| Abstract: | "Sesquiterpenes are particularly interesting as flavorings and fragrances or as pharmaceuticals. Regio- or stereoselective functionalizations of terpenes are one of the main goals of synthetic organic chemistry, which are possible through radical reactions but are not selective enough to introduce the desired chiral alcohol function into those compounds. Cytochrome P450 monooxygenases are versatile biocatalysts and are capable of performing selective oxidations of organic molecules. We were able to demonstrate that CYP109D1 from Sorangium cellulosum So ce56 functions as a biocatalyst for the highly regioselective hydroxylation of norisoprenoids, alpha- and beta-ionone, which are important aroma compounds of floral scents. The substrates alpha- and beta-ionone were regioselectively hydroxylated to 3-hydroxy-alpha-ionone and 4-hydroxy-beta-ionone, respectively, which was confirmed by (1)H NMR and (13)C NMR. The results of docking alpha- and beta-ionone into a homology model of CYP109D1 gave a rational explanation for the regio-selectivity of the hydroxylation. Kinetic studies revealed that alpha- and beta-ionone can be hydroxylated with nearly identical V (max) and K (m) values. This is the first comprehensive investigation of the regioselective hydroxylation of norisoprenoids by CYP109D1" |
| Keywords: | "Bacterial Proteins/chemistry/genetics/*metabolism Cytochrome P-450 Enzyme System/chemistry/genetics/*metabolism Hydroxylation Models, Molecular Myxococcales/*enzymology Norisoprenoids/*metabolism;" |
| Notes: | "MedlineKhatri, Yogan Girhard, Marco Romankiewicz, Anna Ringle, Michael Hannemann, Frank Urlacher, Vlada B Hutter, Michael C Bernhardt, Rita eng Research Support, Non-U.S. Gov't Germany 2010/07/21 Appl Microbiol Biotechnol. 2010 Sep; 88(2):485-95. doi: 10.1007/s00253-010-2756-3. Epub 2010 Jul 20" |
