Structural elucidation of a hy-droxy-cineole product obtained from cytochrome P450 monooxygenase CYP101J2 catalysed transformation of 1,8-cineole

Gavin E Collis; Birgit Unterweger; Geoff J Dumsday; Craig M Forsyth

doi:10.1107/S2056989017010015

Structural elucidation of a hy-droxy-cineole product obtained from cytochrome P450 monooxygenase CYP101J2 catalysed transformation of 1,8-cineole

Acta Crystallogr E Crystallogr Commun. 2017 Jul 21;73(Pt 8):1242-1245. doi: 10.1107/S2056989017010015. eCollection 2017 Jul 1.

Authors

Gavin E Collis¹, Birgit Unterweger^{1

2}, Geoff J Dumsday¹, Craig M Forsyth³

Affiliations

¹ Advanced Fibres and Chemical Industries, CSIRO Manufacturing, Melbourne, Victoria 3169, Australia.
² Infection and Immunity Program, Monash Biomedicine Discovery Institute and Department of Microbiology, Monash University, Clayton 3800, Australia.
³ School of Chemistry, Monash University, Clayton 3800, Australia.

Abstract

1,8-Cineole is an abundant natural product that has the potential to be transformed into other building blocks that could be suitable alternatives to petroleum-based chemicals. Mono-hydroxy-lation of 1,8-cineole can potentially occur at eight different carbon sites around the bicyclic ring system. Using cytochrome P450 monooxygenase CYP101J2 from Sphingobium yanoikuyae B2, the hy-droxy-lation can be regioselectively directed at the C atom adjacent to the methyl-substituted quaternary bridgehead atom of 1,8-cineole. The unambiguous location of the hydroxyl functionality and the stereochemistry at this position was determined by X-ray crystal analysis. The mono-hydroxy-lated compound derived from this microorganism was determined to be (1S)-2a-hy-droxy-1,8-cineole (trivial name) or (1S,4R,6S)-1,3,3-trimethyl-2-oxabi-cyclo-[2.2.2]octan-6-ol (V) (systematic), C₁₀H₁₈O₂. In the solid state this compound exhibits an inter-esting O-H⋯O hydrogen-bonding motif.

Keywords: crystal structure.