A simple synthesis of (S)-(+)-sulcatol, the pheromone of gnathotrichus retusus, employing baker's yeast for asymmetric reduction

Production of (S)-3-hydroxybutyrate by metabolically engineered Saccharomyces cerevisiae

“…An example of such bio-based platform chemicals is 3-hydroxybutyrate (3HB), which is as a precursor for the synthesis of the biodegradable polymer, polyhydroxyalkanoate (PHA) (Lee and Lee, 2003;Tseng et al, 2009;Wang et al, 2013). 3HB exists in the (R)-and (S)-stereoisomeric configurations, and S-3HB and its derivative ethyl S-3HB are used as chiral building blocks for the synthesis of optically active fine chemicals such as antibiotics, vitamins, perfumes, and pheromones (Chiba and Nakai, 1987;Ferrelra and Simonelli, 1990;Lee et al, 2008;Mori, 1981;Zhou et al, 1983).…”

Metabolic Engineering of Escherichia coli for Enhanced Production of ( R )- and ( S )-3-Hydroxybutyrate

“…As a result, the use of biological processes for chiral molecule production has been extensively investigated (4,28,32,36). One example of such a process is the biosynthesis of 3-hydroxybutyric acid (3HB), a versatile chiral molecule containing one hydroxyl group and one carboxyl group, used as a building block for the synthesis of optically active fine chemicals, such as vitamins, antibiotics, pheromones, and flavor compounds (5,6,18,27).…”

Yeast‐Mediated Stereoselective Synthesis

“…The different results of this reduction have been explained by the different conditions: the carbon source was different, but "starving conditions" were applied, and sometimes additives were added for improving the reaction, pretreatment of the cells with ethanol was performed, the reaction was quenched before reaching complete reduction Reduction of heterocyclic keto esters. [233,264,267,268], and many other microorganisms have been used instead of baker's yeast [107,117]. The best results, however, were obtained for the reduction of 62 to (R)-3-hydroxyacetoacetate using Thermoanaerobium brockii [269].…”