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

Abstract

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.

Yeast‐mediated stereo‐selective reduction of estrone by continuous cell culture with dual stirred tanks for product yield improvement

“…The culture medium contained 1.5 g KH 2 PO 4 , 2.9 g K 2 HPO 4 , 1.3 g (NH 4 ) 2 SO 4 , 1.8 g MgSO 4 •7H 2 O, 0.0175 g CaCl 2 •2H 2 O, 0.1 mL (1.25%, w/v) FeSO 4 , 20.0 g D‐(+)‐glucose, and 1.0 L distilled water. The cell growing procedure and conditions were the same as mentioned in our previous work 10…”

“…Immobilization of the microbial cell has also been used frequently to overcome the problem 7, 8. Recently, a biphasic cell culture with organic and aqueous reaction medium were introduced to reduce both substrate and product inhibition and to enhance the yield and stereo‐selectivity for water insoluble substrates 9–11. Also, an effective biotransformation of cholesterol performed under a cloud point system of the nonionic surfactant was reported in the literature 12.…”

Online capillary solid-phase microextraction coupled liquid chromatography-mass spectrometry for analysis of chiral secondary alcohol products in yeast catalyzed stereoselective reduction cell culture

“…The flask was then transferred to an orbital shaker incubator for growing the cells 2 days at a shaking speed 150 rpm and an incubation temperature 30 • C [7]. Ten millimeters of the yeast grown cell culture were taken for dry cell mass measurement after filtering through a micro-porous membrane filter (Nylon, 47 mm dia., 0.22 m).…”

“…This paper focuses on the development of online SPME coupled liquid chromatography-electrospray ionization-ion trap mass spectrometric method for performing efficient chiral separation and analysis [7,[48][49][50][51][52] of trace secondary alcohol products R-and S-4-phenyl-2-butanol in a salt rich cell culture which was associated with the baker yeast S. cerevisiae catalyzed stereoselective biotransformation of the model compound 4-phenyl-2-butanone. In this method manual one-time fixed amount sample injection and online dual column switching technique were used to reach the goals of salt interference reduction, accurate, precise, and sensitive analysis.…”

“…For instances, the catalysis of ketones was performed by adding yeast powder to pure glycerol medium with a high yield and a high enantiomeric excess (e.e.) value [4][5][6], the yeast mediated bio-reduction was proceeded by using hexane/water biphasic cell culture to improve the enantioselectivity and yield [7].…”