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.
Highlights
Terpenoids are group of compounds of natural origin biosynthesized from isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP)
Condensation of IPP and DMAPP leads to geranyl pyrophosphate (GPP, C10) which is a precursor in biosynthesis of monoterpenoids and iridoids
We have described five main reaction types that microorganisms can conduct on terpenes and terpenoids
Summary
Terpenoids are group of compounds of natural origin biosynthesized from isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). S. Lochyński Institute of Cosmetology, Wrocław College of Physiotherapy, Kościuszki 4, 50–038 Wrocław, Poland they are saturated and unsaturated cyclic and aliphatic hydrocarbons with varying degrees of oxygenation, including alcohols, aldehydes, ketones, and carboxylic acids. Terpenoids can be divided into subclasses according to number of isoprene units in their structure. Condensation of IPP and DMAPP leads to geranyl pyrophosphate (GPP, C10) which is a precursor in biosynthesis of monoterpenoids and iridoids. Reaction between GPP and IPP gives farnesyl pyrophosphate (FPP, C15)–precursor in biosynthesis of sesquiterpenoids and sesquiterpenoid lactones. Condensation of two units of FPP leads to triterpenoids (C30). We can distinguish diterpenoids class (C20) which originate from geranylgeranyl pyrophosphate
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