Stereochemical control of microbial reduction. 17. A method for controlling the enantioselectivity of reductions with bakers' yeast
About: This article is published in Journal of Organic Chemistry.The article was published on 1991-07-01. It has received 188 citations till now.
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TL;DR: In this article, a review of recent advances in the asymmetric reduction of ketones by biocatalysts is presented, with a discussion on recent developments in methodologies to control enantioselectivities of catalytic reactions.
Abstract: Herein we review recent advances in the asymmetric reduction of ketones by biocatalysts. Included are discussions on recent developments in methodologies to control enantioselectivities of catalytic reactions, and examples of practical applications that reduce various types of ketones are also shown.
458 citations
TL;DR: This review focuses on the establishment of a novel bioreduction system using an Escherichia coli transformant co-expressing genes for carbonyl reductase and cofactor-regeneration enzyme that could be useful as an all-purpose catalyst for asymmetric reduction reactions.
Abstract: Chiral alcohols are useful intermediates for many pharmaceuticals and chemicals. Enzymatic asymmetric reduction of prochiral carbonyl compounds is a promising method for producing chiral alcohols. There have been many attempts to construct bioreduction systems for the industrial production of chiral alcohols. This review focuses on the establishment of a novel bioreduction system using an Escherichia coli transformant co-expressing genes for carbonyl reductase and cofactor-regeneration enzyme. This bioreduction system could be useful as an all-purpose catalyst for asymmetric reduction reactions.
210 citations
Cites background from "Stereochemical control of microbial..."
...…baker0s yeast or related strains as a catalyst for the asymmetric reduction of many kinds of carbonyl compounds have been made (Chin-Joe et al. 2001; Csuk and Gl nzer 1991; D0Arrigo et al. 1997; Kometani et al. 1993; Nakamura et al. 1991; Shieh et al. 1985; Ward and Young 1990; Zhou et al. 1983)....
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TL;DR: The results demonstrate not only that individual yeast reductases can be used to supply important chiral building blocks, but that GST-fusion proteins allow rapid identification of synthetically useful biocatalysts (along with their corresponding genes).
Abstract: Eighteen key reductases from baker's yeast (Saccharomyces cerevisiae) have been overproduced in Escherichia coli as glutathione S-transferase fusion proteins. A representative set of α- and β-keto esters was tested as substrates (11 total) for each purified fusion protein. The stereoselectivities of β-keto ester reductions depended both on the identity of the enzyme and the substrate structure, and some reductases yielded both l- and d-alcohols with high stereoselectivities. While α-keto esters were generally reduced with lower enantioselectivities, it was possible in all but one case to identify pairs of yeast reductases that delivered both alcohol antipodes in optically pure form. Taken together, the results demonstrate not only that individual yeast reductases can be used to supply important chiral building blocks, but that GST-fusion proteins allow rapid identification of synthetically useful biocatalysts (along with their corresponding genes).
177 citations
TL;DR: Improved stereoselectivity in dehydrogenase-mediated reductions has been achieved by rationally designed gene overexpression and knockouts in Saccharomyces cerevisiae cells and by isolating and characterizing novel dehydrogenases from other organisms.
162 citations
TL;DR: This cross-coupling reaction occurs via an S(N)2 mechanism with inversion of configuration and therefore provides a general approach for the stereocontrolled formation of C-C bonds between two tertiary carbons from chiral secondary alcohols.
Abstract: Practical catalytic cross-coupling of secondary alkyl electrophiles with secondary alkyl nucleophiles under Cu catalysis has been realized. The use of TMEDA and LiOMe is critical for the success of the reaction. This cross-coupling reaction occurs via an SN2 mechanism with inversion of configuration and therefore provides a general approach for the stereocontrolled formation of C–C bonds between two tertiary carbons from chiral secondary alcohols.
155 citations