Related Experiment Video
Updated: Aug 15, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Stereoselective biotransformation of limonene and limonene oxide by cyanobacterium, Synechococcus sp. PCC 7942
Hiroki Hamada1, Yoko Kondo, Kohji Ishihara
1Department of Applied Science, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan. hamada@das.ous.ac.jp
Abstract:
The biotransformation of limonene and limonene oxide by the cyanobacterium, Synechococcus sp. PCC 7942, was investigated. (S)-(+)-Limonene was hydroxylated stereo- and regioselectively at its allylic position of the endocyclic C=C double bond by the cyanobacterial cells to its corresponding alcohol. The cells also showed the ability for the enantio- and stereoselective cleavage of the epoxide group of (1S,2R,4R)-limonene oxide to give (1S,2S,4R)-limonene-1,2-diol. The repetitive production of carveol from limonene was achieved using Ca2+-alginate-immobilized cyanobacterial cells.
Related Concept Videos
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Hydroboration-Oxidation of Alkenes
Microbial Bioremediation of Pesticides
Bioremediation
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

