Biocatalytic Methods for the Synthesis of Enantioenriched Odor Active Compounds

Brenna, Elisabetta; Fuganti, Claudio; Gatti, Francesco G.; Serra, Stefano

doi:10.1021/cr100289r

Cited by 82 publications

(50 citation statements)

References 227 publications

(184 reference statements)

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“…For the reduction of β-hydroxyketones 7a – c , we first chose Baker’s yeast alcohol dehydrogenase (ADH) and oxidoreductases from Saccharomyces cerevisiae ( S. cerevisiae ) and Lactobacillus kefir ( L. kefir ) as these enzymes have been reported to catalyze the enantioselective reduction of 4-phenyl-4-hydroxy-2-butanone [55]. However, Baker’s yeast ADH and S. cerevisiae ADH were not very effective for the reduction of 7a (entries 1 and 2 in Table 9).…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Chiral Zn2+ Complexes Mimicking Natural Aldolases for Catalytic C–C Bond Forming Reactions in Aqueous Solution

Itoh

Sonoike

Kitamura

et al. 2014

IJMS

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Extending carbon frameworks via a series of C–C bond forming reactions is essential for the synthesis of natural products, pharmaceutically active compounds, active agrochemical ingredients, and a variety of functional materials. The application of stereoselective C–C bond forming reactions to the one-pot synthesis of biorelevant compounds is now emerging as a challenging and powerful strategy for improving the efficiency of a chemical reaction, in which some of the reactants are subjected to successive chemical reactions in just one reactor. However, organic reactions are generally conducted in organic solvents, as many organic molecules, reagents, and intermediates are not stable or soluble in water. In contrast, enzymatic reactions in living systems proceed in aqueous solvents, as most of enzymes generally function only within a narrow range of temperature and pH and are not so stable in less polar organic environments, which makes it difficult to conduct chemoenzymatic reactions in organic solvents. In this review, we describe the design and synthesis of chiral metal complexes with Zn2+ ions as a catalytic factor that mimic aldolases in stereoselective C–C bond forming reactions, especially for enantioselective aldol reactions. Their application to chemoenzymatic reactions in aqueous solution is also presented.

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Chiral Zn2+ Complexes Mimicking Natural Aldolases for Catalytic C–C Bond Forming Reactions in Aqueous Solution

Itoh

Sonoike

Kitamura

et al. 2014

IJMS

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“…It is also used as an aroma ingredient of flavored sweets and beverages, as well as a variety of baked foods and tobacco. Four stereoisomers of whisky lactone are known, and their olfactory properties are determined by their spatial structure [12]. γ-Decalactone was originally isolated from fruits, meat, and dairy products.…”

Section: Introductionmentioning

confidence: 99%

Microbial Kinetic Resolution of Aroma Compounds Using Solid-State Fermentation

et al. 2018

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A novel microbial approach to the production of enantiomerically enriched and pure aroma compounds based on kinetic resolution via solid-state fermentation is proposed. Twenty-five filamentous fungi were screened for lipase activity and enantioselective hydrolysis of a volatile racemic ester (1-phenylethyl acetate (1)) and several racemic lactones (trans and cis whisky lactones (4, 5), γ-decalactone (7), δ-decalactone (8), (cis-3a,4,7,7a-tetrahydro-1(3H)-isobenzofuranone) (9)). Solid-state fermentation was conducted with linseed and rapeseed cakes. Kinetic resolution afforded enantiomerically enriched products with high enantiomeric excesses (ee = 82-99%). The results highlight the potential economic value of solid-state fermentation using agroindustrial side-stream feedstocks as an alternative to more expensive processes conducted in submerged fermentation.

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“…The phenomenon of the enantioselectivity in odour perception has been intensively investigated in the last years [1]. Human olfactory receptors are chiral and can discriminate the two enantiomers of a chiral odorous molecule [2].…”

Section: Introductionmentioning

confidence: 99%