Abstract
Thirteen Non-Conventional Yeasts (NCYs) have been investigated for their ability to reduce activated C=C bonds of chalcones to obtain the corresponding dihydrochalcones. A possible correlation between bioreducing capacity of the NCYs and the substrate structure was estimated. Generally, whole-cells of the NCYs were able to hydrogenate the C=C double bond occurring in (E)-1,3-diphenylprop-2-en-1-one, while worthy bioconversion yields were obtained when the substrate exhibited the presence of a deactivating electron-withdrawing Cl substituent on the B-ring. On the contrary, no conversion was generally found, with a few exceptions, in the presence of an activating electron-donating substituent OH. The bioreduction aptitude of the NCYs was apparently correlated to the logP value: Compounds characterized by a higher logP exhibited a superior aptitude to be reduced by the NCYs than compounds with a lower logP value.
Highlights
The chemoselective bioreduction of α,β-unsaturated alkenes represents an important tool in the synthesis of a lot of fine chemicals and pharmaceuticals [1,2,3]
Flavin-dependent oxidoreductases, which have been extensively studied for their ability to catalyze the asymmetric reduction of electronically activated C=C bonds, possessing electron-withdrawing substituents in the presence of cofactor-recycling systems for NAD(P)H [4,5,6,7,8,9,10,11,12,13,14]
Worthy bioconversion yields were obtained when the substrate exhibited the presence of a deactivating electron-withdrawing Cl substituent on the B-ring (2a): all the Non-Conventional Yeasts (NCYs) exhibited the ability to reduce C=C double bond of 2a with bioconversion yields ranging from 8% to
Summary
The chemoselective bioreduction of α,β-unsaturated alkenes represents an important tool in the synthesis of a lot of fine chemicals and pharmaceuticals [1,2,3]. Ene-reductases (ERs) belong to the flavin-containing “Old Yellow Enzyme” family (OYE, EC 1.6.99.1), which includes a class of I flavin-dependent oxidoreductases, which have been extensively studied for their ability to catalyze the asymmetric reduction of electronically activated C=C bonds, possessing electron-withdrawing substituents in the presence of cofactor-recycling systems for NAD(P)H [4,5,6,7,8,9,10,11,12,13,14]. Chalcones represent an interesting class of bioactive open-chain flavonoids, exhibiting α,β-unsaturated carbonyl groups in their scaffolds. Some studies proved their important antitubercular [26], antioxidant [27], antifungal [28] and anticancer [29] activities.
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