Biotransformation of (±)-α-ionone and β-ionone by cultured cells of Caragana chamlagu

Zeng

J Ind Microbiol Biotechnol

et al. 2008

As an important organic compound, chiral alcohols are the key chiral building blocks to many single enantiomer pharmaceuticals. Asymmetric reduction of the corresponding prochiral ketones to produce the chiral alcohols by biocatalysis is one of the most promising routes. Asymmetric reduction of different kinds of non-natural prochiral ketones catalyzed by various plants tissue was studied in this work. Acetophenone, 4'-chloroacetophenone and ethyl 4-chloroacetoacetate were chosen as the model substrates for simple ketone, halogen-containing aromatic ketone and beta-ketoesters, respectively. Apple (Malus pumila), carrot (Daucus carota), cucumber (Cucumis sativus), onion (Allium cepa), potato (Soanum tuberosum), radish (Raphanus sativus) and sweet potato (Ipomoea batatas) were chosen as the biocatalysts. It was found that these kinds of prochiral ketoness could be reduced by these plants tissue with high enantioselectivity. Both R- and S-form configuration chiral alcohols could be obtained. The e.e. and chemical yield could reach about 98 and 80% respectively for acetophenone and 4'-chloroacetophenone reduction reaction with favorable plant tissue. And the e.e. and yield for ethyl 4-chloroacetoacetate reduction reaction was about 91 and 45% respectively.

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Zeng

J Ind Microbiol Biotechnol

et al. 2008

“…We have developed particularly the use of plant cultured cells for the biotransformation of natural products such as thujopsene (Sakamaki et al 2001), ionone (Sakamaki et al 2004) and valencene and unnatural substrates such as 1,2-diketone (Chai et al 2003a), bisphenol-A (Chai et al 2003b) and 3-acetylisoxazoles .…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of zerumbone by Caragana chamlagu

et al. 2008

Self Cite

J of Chemical Tech & Biotech

“…One of the major reactions performed with alcohol dehydrogenase in baker's yeast is the enantioselective reduction of carbonyl group in prochiral ketones to give one configuration of the chiral alcohol 3. The importance of chiral alcohols and their derivatives can be attributed to their serving as the chiral building blocks of pheromones,4 fragrance,5 pharmaceuticals and other chemicals 6–9. The enantioselective synthesis of chiral alcohols can be achieved using catalytic organometallic reagents; however, chiral alcohol production using either whole yeast cell10, 11 or isolated alcohol dehydrogenase,12, 13 either immobilized14, 15 or not immobilized,16, 17 is still favored for reasons of stability and ease of product recovery.…”

Section: Introductionmentioning

confidence: 99%

Yeast‐mediated enantioselective synthesis of chiral R‐(+)‐ and S‐(−)‐1‐phenyl‐1‐butanol from prochiral phenyl n‐propyl ketone in hexane–water biphasic culture

Cheng¹,

Tsai²

2008

BACKGROUND: The hydrophobic phenyl n-propyl ketone was used as a model compound to examine alcohol dehydrogenase activity in Saccharomyces cerevisiae mediated cell culture. Parameters such as pH, hexane-towater volume percentage, and the amount of cofactor Zn 2+ ion for either cell growth or reduction were studied to see their effect on the enantioselectivity toward the product R-(+)-or S-(−)-1-phenyl-1-butanol.