Application of microorganisms towards synthesis of chiral terpenoid derivatives

Abstract

Biotransformations are a standard tool of green chemistry and thus are following the rules of sustainable development. In this article, we describe the most common types of reactions conducted by microorganisms applied towards synthesis of chiral terpenoid derivatives. Potential applications of obtained products in various areas of industry and agriculture are shown. We also describe biological activity of presented compounds. Stereoselective hydroxylation, epoxidation, Baeyer-Villiger oxidation, stereo- and enantioselective reduction of ketones, and various kinetic resolutions carried out by bacteria and fungi have been reviewed. Mechanistic considerations regarding chemical and enzymatic reactions are presented. We also briefly describe modern approaches towards enhancing desired enzymatic activity in order to apply modified biocatalysts as an efficient tool and green alternative to chemical catalysts used in industry.

Fig. 1

Biotransformation of (−)-menthol by R. solani and (−)-α-pinene by B. cinerea

Fig. 2

Biotransformation of (R)-(+)-limonene by Penicillium species and 4,4,6-trimethyl-9-oxabicyclo[4.3.0]non-2-en-8-one with A. cylindrospora

Fig. 3

Biotransformation of (±)-dihydrocarvone by A. calcoaceticus

Fig. 4

Biotransformation of (4R)-(−)-carvone by T. cutaneum CCT 1903

Fig. 5

Biotransformations by Hormonema sp. UOFS Y-0067

Fig. 6

Reduction of (4R)-carvone by G. butleri, D. grovesii, and S. octosporus

Fig. 7

Biotransformation of (4S)-carvone by G. butleri, D. grovesii, and S. octosporus

Fig. 8

Profile of reduction of carvone stereoisomers with selected biocatalysts

Fig. 9

Kinetic resolution of (+)-(1R,2S,4R)-1,2-epoxylimonene and (+)-(1S,2R,4R)-1,2-epoxylimonene using R. erythropolis DCL14 as a biocatalyst

Fig. 10

Kinetic resolution of (−)-(4R,6R)-carveol and (−)-(4R,6S)-carveol with R. erythropolis DCL14