A thermodynamic study of the ketoreductase-catalyzed reduction of 2-alkanones in non-aqueous solvents

Tewari, Yadu B.; Schantz, Michele M.; Phinney, Karen W.; Rozzell, J. David

doi:10.1016/j.jct.2004.08.002

Cited by 10 publications

(12 citation statements)

References 26 publications

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“…The present study of 1-phenyl-1-alkanone is similar to our previous studies of 2-alkanone reactions [21]. Comparing the two studies, the phenyl group in the 1-phenyl-1-alkanone reaction replaces the methyl group of the 2-alkanone reactions.…”

Section: Results Of Equilibrium Measurementssupporting

confidence: 88%

“…The method of analysis of the reactants and products in the equilibrated reaction mixtures in n-hexane and n-pentane was similar to the method described previously [21,22]. For quantitative analysis % 4 cm 3 of reaction mixture and %0.10 cm 3 of internal standard solution (1-hexanol) were gravimetrically added to a vial, and tightly capped.…”

Section: Equilibrium Studiesmentioning

confidence: 99%

“…A small amount of b-nicotinamide-adenine dinucleotide (reduced), {NAD(red)} is required for catalytic activity of this ketoreductase. As described in our previous papers [21,22], the ketoreductase catalyzed reactions proceed in two steps. In the first step, the 1-phenyl-1-alkanone is reduced to the corresponding 1-phenyl-1-alkanol and NAD(ox).…”

Section: Introductionmentioning

confidence: 96%

“…There have been several studies from our laboratory dealing with the thermodynamics of enzyme-catalyzed reactions in organic solvents [17][18][19][20][21][22]. The thermodynamic results obtained in these studies are essential for the basic understanding of the energetics of these reactions and also for the practical utilization of enzyme-catalyzed reduction reactions of 1-phenyl-1-alkanone in non-aqueous solvents.…”

Section: Introductionmentioning

confidence: 99%

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A thermodynamic study of ketoreductase-catalyzed reactions 3. Reduction of 1-phenyl-1-alkanones in non-aqueous solvents

Tewari

Kishore

Rozzell³

et al. 2006

The Journal of Chemical Thermodynamics

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Section: Results Of Equilibrium Measurementssupporting

confidence: 88%

Section: Equilibrium Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A thermodynamic study of ketoreductase-catalyzed reactions 3. Reduction of 1-phenyl-1-alkanones in non-aqueous solvents

Tewari

Kishore

Rozzell³

et al. 2006

The Journal of Chemical Thermodynamics

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“…45,63 Use of more complex enzymes, including those that require cofactors and especially oxidoreductases and lyases in organic solvents, is reported using organic solvent as a co-solvent, [64][65][66] but, rarely in a neat organic solvent system. [67][68][69][70][71] …”

Section: Methodsmentioning

confidence: 99%

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

Milner¹,

Maguire²

2012

Arkivoc

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Modern synthetic organic chemistry has experienced an enormous growth in biocatalytic methodologies; enzymatic transformations and whole cell bioconversions have become generally accepted synthetic tools for asymmetric synthesis. This review details an overview of the latest achievements in biocatalytic methodologies for the synthesis of enantiopure compounds with a particular focus on chemoenzymatic synthesis in non-aqueous media, immobilisation technology and dynamic kinetic resolution. Furthermore, recent advances in ketoreductase technology and their applications are also presented.Keywords: Biocatalysis, kinetic and dynamic kinetic resolution, Baker's yeast, ketoreductases General IntroductionAsymmetric synthesis is the preferential formation of one stereoisomer of a chiral target compound to another; when scientists at GlaxoSmithKline, AstraZeneca and Pfizer 1 examined 128 syntheses from their companies, they found as many as half of the drug compounds made by their process research and development groups are not only chiral but also contain an average of two chiral centres each. 2In 2006 just 25 % were derived from the chiral pool and over 50 % employed chiral technologies. 1In order to meet regulatory requirements enantiomeric purities of 99.5 % were deemed necessary by the FDA. 3 This is one of the biggest challenges which face chemists today, primarily due to the recognition of the fact that different enantiomers of the same compound can interact differently in biological systems. As a consequence, the production of single enantiomers instead of racemic mixtures has become an important process in the pharmaceutical and agrochemical industry. Several routes can lead to the desired enantiomer including transition metal-, [4][5][6] organo-5,7-10 and bio-catalysis [11][12][13][14][15] and these have been thoroughly reviewed in the literature. 16,17 2. Biocatalysis IntroductionBiocatalysis involves the use of enzymes or whole cells (containing the desired enzyme or enzyme system) as catalysts for chemical reactions. A timeline of historic events in biocatalysis and biotechnology is outlined in Table 1. [18][19][20] Reviews and Accounts Novel methodologies for discovering industrial enzymes based on genomic sequencing and phage display (discussed further in Section 1.3), 21,22 as well as highly effective optimisation tools based on chemical, physical and molecular biology approaches, 23 have improved the access to biocatalysts, increased their stability, and radically broadened their specificity. 24This greater availability of catalysts with superior qualities including the use of new bioengineering tools contributed significantly to the development of new industrial processes. Biocatalytic methodologies for organic synthesis were outlined by Woodley et al. in three categories: established, emerging and expanding chemistries as depicted in Figure 1. 25 Enzyme classesBy the late 1950s it had become evident that the nomenclature of enzymes without any guiding authority, in a period when the...

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Heterogeneous Catalysis in Supercritical Media: 1. Carbon Dioxide

Kruse

Vogel

2007

Chem Eng & Technol

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Dedicated to Prof. Dr.-Ing. Jens Weitkamp on the occasion of his 65th birthdayOver the past few years, supercritical fluids have received considerable interest as reaction media. Supercritical fluids combine properties of gases and liquids. Densities are lower than in the liquid phase, but significantly higher than in the gas phase. This makes supercritical fluids excellent solvents for a variety of substances. The good dissolution capacity exists only in or near the supercritical range. Reaction products can be separated, for instance, simply by decreasing temperature and pressure. This may be used to intensify the process as complex separation processes, like distillation, are avoided.

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A thermodynamic study of the ketoreductase-catalyzed reduction of 2-alkanones in non-aqueous solvents

Cited by 10 publications

References 26 publications

A thermodynamic study of ketoreductase-catalyzed reactions 3. Reduction of 1-phenyl-1-alkanones in non-aqueous solvents

A thermodynamic study of ketoreductase-catalyzed reactions 3. Reduction of 1-phenyl-1-alkanones in non-aqueous solvents

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

Heterogeneous Catalysis in Supercritical Media: 1. Carbon Dioxide

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