Efficient kinetic resolution of a racemic 7-membered biaryl lactone: enantioselective synthesis of 2,2′-dihydroxymethyl-1,1′-binaphthyl

A novel pathway to enantiomerically pure 2,2′-dihydroxymethyl-1,1′-binaphthyl is described, through kinetic resolution of its racemic 7-membered biaryl lactone precursor. Oxazaborolidine-assisted borane reduction of this lactone proceeds with very high enantioselectivity (k_rel=50). For optimum results on a preparative scale, a ‘three fractions strategy’ is suggested, which combines kinetic resolution and fractional crystallization and leads to both atropisomers in high enantiomeric excess.     

Preparation,purification, and analysis of alkylated cyclodextrins

Methods of alkylation of α-, β- and γ-cyclodextrins have been optimized with regard to the parameters of reaction, degree of alkylation and yields. The analysis of the reaction mixtures and of the isolated single species has been performed by high temperature GC and HPLC. The phase systems of the preferably applied HPLC have been carefully adjusted by variation of both the stationary and mobile phases to the very different hydrophobicities of the various alkylated CD species which have been synthesized. Several partially or fully alkylated CD species were isolated from preparative scale HPLC separations in high purity.     

Enzymatic Conversion of Flavonoids using Bacterial Chalcone Isomerase and Enoate Reductase

Flavonoids are a large group of plant secondary metabolites with a variety of biological properties and are therefore of interest to many scientists, as they can lead to industrially interesting intermediates. The anaerobic gut bacterium Eubacterium ramulus can catabolize flavonoids, but until now, the pathway has not been experimentally confirmed. In the present work, a chalcone isomerase (CHI) and an enoate reductase (ERED) could be identified through whole genome sequencing and gene motif search. These two enzymes were successfully cloned and expressed in Escherichia coli in their active form, even under aerobic conditions. The catabolic pathway of E. ramulus was confirmed by biotransformations of flavanones into dihydrochalcones. The engineered E. coli strain that expresses both enzymes was used for the conversion of several flavanones, underlining the applicability of this biocatalytic cascade reaction.     

Mikrochemie

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