Screening of some vegetables for the biotransformation of bicyclo[3.3.1]nonane-2,6-diol diacetate

Abstract

Vegetables as biocatalysts were screened for the stereoselective biotransformation of racemic bicyclo[3.3.1]nonane-2,6-diol diacetate. The best results were obtained using the roots of carrot (Daucus carota) and parsnip (Pastinaca sativa) and the rootstocks of ginger (Zingiber officinale). During the biotransformation of racemic bicyclo[3.3.1]nonane-2,6-diol diacetate the enzymatic hydrolysis took place. Under different reaction conditions, i.e. the reaction temperature and time, and using different plant material as biocatalyst, (1R,2R,5R,6R)-(+)-bicyclo[3.3.1]nonane-2,6-diol monoacetate or (1S,2S,5S,6S)-(-)-bicyclo[3.3.1]nonane-2,6-diol monoacetate were obtained as reaction products. (–)- Enantiomer with the optical purity of 29.3% was obtained at 25°C using parsnip as biocatalyst for 2 days and (+)- enantiomer with the optical purity of 44.1% was obtained at 30°C using carrot for 3 days.

Keywords

• racemic bicyclo[3.3.1]nonane-2,6-diol diacetate
• stereoselective biotransformation
• vegetables