Applied Microbiology and Biotechnology

, Volume 88, Issue 2, pp 485–495 | Cite as

Regioselective hydroxylation of norisoprenoids by CYP109D1 from Sorangium cellulosum So ce56

  • Yogan Khatri
  • Marco Girhard
  • Anna Romankiewicz
  • Michael Ringle
  • Frank Hannemann
  • Vlada B. Urlacher
  • Michael C. Hutter
  • Rita Bernhardt
Biotechnological Products and Process Engineering

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, α- and β-ionone, which are important aroma compounds of floral scents. The substrates α- and β-ionone were regioselectively hydroxylated to 3-hydroxy-α-ionone and 4-hydroxy-β-ionone, respectively, which was confirmed by 1H NMR and 13C NMR. The results of docking α- and β-ionone into a homology model of CYP109D1 gave a rational explanation for the regio-selectivity of the hydroxylation. Kinetic studies revealed that α- and β-ionone can be hydroxylated with nearly identical Vmax and Km values. This is the first comprehensive investigation of the regioselective hydroxylation of norisoprenoids by CYP109D1.

Keywords

Terpenoids Norisoprenoids Cytochromes P450 CYP109D1 Sorangium cellulosum So ce56 

Supplementary material

253_2010_2756_MOESM1_ESM.doc (498 kb)
ESM1(DOC 497 kb)

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Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Yogan Khatri
    • 1
  • Marco Girhard
    • 2
  • Anna Romankiewicz
    • 3
  • Michael Ringle
    • 1
  • Frank Hannemann
    • 1
  • Vlada B. Urlacher
    • 2
  • Michael C. Hutter
    • 4
  • Rita Bernhardt
    • 1
    • 5
  1. 1.Department of BiochemistrySaarland UniversitySaarbrückenGermany
  2. 2.Institute of BiochemistryHeinrich-Heine-Universitaet DüsseldorfDüsseldorfGermany
  3. 3.Institute of Technical BiochemistryUniversitaet StuttgartStuttgartGermany
  4. 4.Center for BioinformaticsSaarland UniversitySaarbrückenGermany
  5. 5.Institut für BiochemieUniversität des SaarlandesSaarbrückenGermany

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