New Alcohol Dehydrogenases for the Synthesis of Chiral Compounds

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.

New Alcohol Dehydrogenases for the Synthesis of Chiral ..

New alcohol dehydrogenases for the synthesis of chiral compounds.
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Synthetic Organic Chemistry resume in Seoul, South …

Terpenoids are applied in varying areas of human interest: flavor and fragrance industry–volatile monoterpenoids like citronellal, citral, geraniol, (−)-menthol; pharmaceutical industry–anticancer agent taxol; agriculture–iridoids and sesquiterpene lactones which are used as insect feeding deterrents (Walton and Brown ). Despite variety of applications and activity of terpenoids, there are attempts to modify their base structure to enhance their properties. This can be achieved by applying chemical synthesis or biotransformations. In many cases, organic synthesis is not a method of choice of structural modifications of complicated terpenoids due to side reactions, low regio- and enantioselectivity, low yields, and application of expensive catalysts comprising transition metal ions.

New alcohol dehydrogenases for synthesis of ..

Terpenoids are group of compounds of natural origin biosynthesized from isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). Structurally, 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). Among them are limonoids, cardenolides, quassinoids, cucrbitacins, saponins, and phytosterols. From terpenoids, we can also distinguish diterpenoids class (C20) which originate from geranylgeranyl pyrophosphate.

Stereoselective Enzymatic Synthesis of Chiral Alcohols with the Use of a Carbonyl Reductase from Candida magnoliae with Anti-Prelog Enantioselectivity
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EP0796914A3 - Alcohol dehydrogenase and its use in …

In our effort to search for carbonyl reductases with anti-Prelog enantioselectivity, the activity and enantioselectivity of a carbonyl reductase from have been examined with various ketones of diverse structures. This carbonyl reductase catalyzed the reduction of a series of ketones, α- and β-ketoesters, to anti-Prelog configurated alcohols in excellent optical purity. The usefulness of this carbonyl reductase has been demonstrated by synthesis of several chiral alcohol intermediates of pharmaceutical importance.

of asymmetric compounds, and in new ..

1.1 Dehydrogenases as Catalysts for the Synthesis of Chiral Compounds