An enzymatic citral asymmetric reduction method capable of increasing optical purity of (R)-citronellal

Abstract

An enzymatic citral asymmetric reduction method capable of increasing optical purity of (R)-citronellal is disclosed, namely a method coupling an amino-acid-catalyzed citral cis-trans isomerization reaction and a citral asymmetric hydrogenation reaction catalyzed by a saccharomyces cerevisiae enol reductase OYE1 to increase the optical purity of the (R)-citronellal that is a product of citral hydrogenation. When citral cis-trans isomers are subjected to the asymmetric hydrogenation reaction catalyzed by the saccharomyces cerevisiae enol reductase OYE1 to synthesize the (R)-citronellal, the (R)-citronellal is derived from trans-citral, (S)-citronellal is derived from cis-citral, and the catalysis speed for the trans-citral is higher than that for the cis-citral. Through coupling with the amino-acid-catalyzed citral cis-trans isomerization reaction, a part of the cis-citral is converted into the trans-citral, thus greatly increasing the ee value of the product that is the (R)-citronellal. In a catalytic system having a volume of 10 mL, 100 mg / mL of glycine is added, after 50 mM citral is subjected to a catalytic reaction for 4 h, the ee value of the (R)-citronellal is 65.4%, and is increased by 48.7% when being compared with the ee value of (R)-citronellal when the cis-trans isomerization reaction is not coupled.

Description

(1) Technical field

[0001] The invention relates to a method for synthesizing (R)-citronellal by enol reductase-catalyzed asymmetric hydrogenation of citral, in particular to a cis-trans isomerization of citral through the enzymatic asymmetric hydrogenation of citral and amino acid catalysis A method for coupling the reaction phases to improve the optical purity of the hydrogenated product (R)-citronellal. (2) Background technology

[0002] Citral is a terpene fatty aldehyde with the molecular formula C 10 H 16 O, with a strong lemon aroma, is a spice with broad application prospects. At present, the industrial production of citral is mainly chemical methods, including dehydrolinalool transposition method and prenyl alcohol and prenaldehyde condensation rearrangement synthesis method. There are two stereoisomers of citral, whether extracted from natural products or derived from chemical synthesis: cis-citral (neral) and trans-citral (geranial). Amino acids can catalyze t...

Images