Reference of (S)-Methyl 3-hydroxybutanoate. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: (S)-Methyl 3-hydroxybutanoate, is researched, Molecular C5H10O3, CAS is 53562-86-0, about Highly Stereoselective Reagents for β-Keto Ester Reductions by Genetic Engineering of Baker’s Yeast. Author is Rodriguez, Sonia; Kayser, Margaret M.; Stewart, Jon D..
While whole cells of baker’s yeast (Saccharomyces cerevisiae) are a convenient biocatalytic reducing agent for a wide variety of carbonyl compounds, mixtures of stereoisomeric alcs. are often observed since the organism contains a large number of reductase enzymes with overlapping substrate specificities but differing stereoselectivities. We sought to improve the performance of baker’s yeast for β-keto ester reductions by using recombinant DNA techniques to alter the levels of three enzymes known to play important roles in these reactions (fatty acid synthase, Fasp; aldo-keto reductase, Ypr1p; α-acetoxy ketone reductase, Gre2p). A complete set of “”first-generation”” yeast strains that either lack or overexpress each of these three enzymes was created and tested for improvements in stereoselective reductions of a series of β-keto esters. On the basis of these results, multiply modified (“”second-generation””) strains were created that combined gene knockout and overexpression in single strains. In some cases, these addnl. modifications further improved the stereoselectivities of β-keto ester reductions, thereby making several β-hydroxy ester building blocks readily available by reactions that can be performed by nonspecialists. This work also revealed that addnl. yeast proteins participate in reducing β-keto esters, and further progress using this strategy will require either addnl. genetic manipulations or the expression of yeast reductases in hosts that lack enzymes with overlapping substrate specificity.
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