The dynamic kinetic resolution of 3-oxo-4-phenyl-β-lactam by recombinant E. coli overexpressing yeast reductase Ara1p

Yang, Yan; Drolet, Melissa; Kayser, Margaret M.

doi:10.1016/j.tetasy.2005.07.029

Cited by 23 publications

(8 citation statements)

References 32 publications

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“…[41] What is key in this case is the importance of the experimental conditions. In a shake-flask, Ara1P yielded a 1.4:1 mixture of diastereomers (both in 99% ee).…”

Section: β-Keto Ester Reductionmentioning

confidence: 99%

Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis

Applegate

Berkowitz

2015

Adv Synth Catal

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Over the past two decades, the domains of both frontline synthetic organic chemistry and process chemistry and have seen an increase in crosstalk between asymmetric organic/organometallic approaches and enzymatic approaches to stereocontrolled synthesis. This review highlights the particularly auspicious role for dehydrogenase enzymes in this endeavor, with a focus on dynamic reductive kinetic resolutions (DYRKR) to “deracemize” building blocks, often setting two stereocenters in so doing. The scope and limitations of such dehydrogenase-mediated processes are overviewed, as are future possibilities for the evolution of enzymatic DYRKR.

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“…[41] What is key in this case is the importance of the experimental conditions. In a shake-flask, Ara1P yielded a 1.4:1 mixture of diastereomers (both in 99% ee).…”

Section: β-Keto Ester Reductionmentioning

confidence: 99%

Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis

Applegate

Berkowitz

2015

Adv Synth Catal

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“…As a result, cis-(3S,4R)-3-hydroxy-4-phenyl-b-lactam was obtained as a single enantiopure product. 134 Figure 77 shows dynamic kinetic resolution of 2-substituted esters having an aldehyde group at 3 position to optically active 3-hydroxyesters. 6a,135-138 The enantioselectivity can be controlled by changing the ester group for the baker's yeast reduction.…”

Section: Dynamic Kinetic Resolution Through Reductionmentioning

confidence: 99%

Recent progress in biocatalysis for asymmetric oxidation and reduction

Matsuda

Yamanaka

Nakamura

2009

Tetrahedron: Asymmetry

364

163

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“…Recently, Fulop and coworkers 44 reported lipase-catalysed kinetic and DKR of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ethyl ester (rac)- (18) to produce enantiopure (R)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (19). The drugs containing the isoquinoline skeleton can be applied to a wide range of therapies.…”

Section: Enzymatic Hydrolysismentioning

confidence: 99%

“…Much have been written especially on its ability to catalyse reduction reaction on a and b-ketoesters. [17][18][19] Other types of organisms with similar ability as that of baker's yeast are tabulated in Table 1.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic and microbial dynamic kinetic resolutions

et al. 2008

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This review tracks a decade of dynamic kinetic resolution developments with a biocatalytic inclination using enzymatic/microbial means for the resolution part followed by the racemization reactions either by means of enzymatic or chemocatalyst. These fast developments are due to the ability of the biocatalysts to significantly reduce the number of synthetic steps which are common for conventional synthesis. Future developments in novel reactions and products of dynamic kinetic resolutions should consider factors that are needed to be extracted at the early synthetic stage to avoid inhibition at scale-up stage have been highlighted.

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The dynamic kinetic resolution of 3-oxo-4-phenyl-β-lactam by recombinant E. coli overexpressing yeast reductase Ara1p

Cited by 23 publications

References 32 publications

Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis

Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis

Recent progress in biocatalysis for asymmetric oxidation and reduction

Chemoenzymatic and microbial dynamic kinetic resolutions

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