Stereoselective determination of 2-benzamidomethyl-3-oxobutanoate and methyl-2-benzoylamide-3-hydroxybutanoate by chiral high-performance liquid chromatography in biotransformation

Chen, Xiang; Zheng, Yu‐Guo; Liu, Zhi‐Qiang; Sun, Li‐Hui

doi:10.1016/j.jchromb.2014.10.020

Cited by 5 publications

(2 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Strain CCTCC M 2012379 was cultivated as described previously [ 44 ]. The genomic DNA of this strain was extracted using a FastDNA® Spin Kit for Soil (MPBio, Shanghai, China).…”

Section: Methodsmentioning

confidence: 99%

Efficient biosynthesis of ethyl (R)-4-chloro-3-hydroxybutyrate using a stereoselective carbonyl reductase from Burkholderia gladioli

et al. 2016

Self Cite

View full text Add to dashboard Cite

BackgroundEthyl (R)-4-chloro-3-hydroxybutyrate ((R)-CHBE) is a versatile chiral precursor for many pharmaceuticals. Although several biosynthesis strategies have been documented to convert ethyl 4-chloro-3-oxobutanoate (COBE) to (R)-CHBE, the catalytic efficiency and stereoselectivity are still too low to be scaled up for industrial applications. Due to the increasing demand of (R)-CHBE, it is essential to explore more robust biocatalyst capable of preparing (R)-CHBE efficiently.ResultsA stereoselective carbonyl reductase toolbox was constructed and employed into the asymmetric reduction of COBE to (R)-CHBE. A robust enzyme designed as BgADH3 from Burkholderia gladioli CCTCC M 2012379 exhibited excellent activity and enantioselectivity, and was further characterized and investigated in the asymmetric synthesis of (R)-CHBE. An economical and satisfactory enzyme-coupled cofactor recycling system was created using recombinant Escherichia coli cells co-expressing BgADH3 and glucose dehydrogenase genes to regenerate NADPH in situ. In an aqueous/octanol biphasic system, as much as 1200 mmol COBE was completely converted by using substrate fed-batch strategy to afford (R)-CHBE with 99.9 % ee at a space-time yield per gram of biomass of 4.47 mmol∙L−1∙h−1∙g DCW−1.ConclusionsThese data demonstrate the promising of BgADH3 in practical synthesis of (R)-CHBE as a valuable chiral synthon. This study allows for the further application of BgADH3 in the biosynthesis of chiral alcohols, and establishes a preparative scale process for producing (R)-CHBE with excellent enantiopurity.Electronic supplementary materialThe online version of this article (doi:10.1186/s12896-016-0301-x) contains supplementary material, which is available to authorized users.

show abstract

“…Strain CCTCC M 2012379 was cultivated as described previously [ 44 ]. The genomic DNA of this strain was extracted using a FastDNA® Spin Kit for Soil (MPBio, Shanghai, China).…”

Section: Methodsmentioning

confidence: 99%

Efficient biosynthesis of ethyl (R)-4-chloro-3-hydroxybutyrate using a stereoselective carbonyl reductase from Burkholderia gladioli

et al. 2016

Self Cite

View full text Add to dashboard Cite

show abstract

“…Furthermore, in the reduction of substrate 9 , we found that L1 , L2 , L6 , and L8 were able to offer very good results (Scheme c), with L8 showing the most satisfactory performance (full conversion, 95% ee and dr = 8:1) (details in Supporting Information Table S2). It is also worth mentioning that product 10 was the precursor of the highly important therapeutic intermediate 4AA, which is widely used in the production of antibiotic drugs. We then tested L1 in Ru-catalyzed asymmetric hydrogenations of unprotected enamine 11 .…”

mentioning

confidence: 99%

Design and Synthesis of Diphosphine Ligands Based on the Chiral Biindolyl Scaffold and Their Application in Transition-Metal Catalysis

Zhang,

Chen,

Zhang

2024

Org. Lett.

View full text Add to dashboard Cite

An extremely concise, scalable, and stereoselective synthesis of a privileged chiral skeleton based on 2,2′-biindolyl and commercially available chiral building blocks has been developed. This novel skeleton allows for easy access to a range of bisphosphine ligands (decagram scale, up to 58% total yield, only three steps). The synthetic method is characterized by an efficient central-to-axial chirality transfer strategy. In particular, the superior performance of the ligands has been demonstrated in diverse reactions, including several asymmetric hydrogenations, asymmetric conjugate reductions, and cycloisomerization reactions, indicating a great potential for the application of the newly developed chiral backbones in further modifications and exploration of novel chiral ligands and catalysts.

show abstract

Chemoenzymatic synthesis of (S)-duloxetine using carbonyl reductase from Rhodosporidium toruloides

Chen

Liu

Chen

et al. 2016

Bioorganic Chemistry

View full text Add to dashboard Cite

Stereoselective determination of 2-benzamidomethyl-3-oxobutanoate and methyl-2-benzoylamide-3-hydroxybutanoate by chiral high-performance liquid chromatography in biotransformation

Cited by 5 publications

References 25 publications

Efficient biosynthesis of ethyl (R)-4-chloro-3-hydroxybutyrate using a stereoselective carbonyl reductase from Burkholderia gladioli

Efficient biosynthesis of ethyl (R)-4-chloro-3-hydroxybutyrate using a stereoselective carbonyl reductase from Burkholderia gladioli

Design and Synthesis of Diphosphine Ligands Based on the Chiral Biindolyl Scaffold and Their Application in Transition-Metal Catalysis

Chemoenzymatic synthesis of (S)-duloxetine using carbonyl reductase from Rhodosporidium toruloides

Contact Info

Product

Resources

About