Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures

Chadha, Anju; Manohar, Madhura; Soundararajan, T.; Lokeswari, T. S.

doi:10.1016/0957-4166(96)00183-8

Cited by 45 publications

(18 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[9] Besides, Chadha et al reported that the enantioselective reduction of ethyl 2-oxophenylbutyrate to ethyl (R)-2-hydroxy-4-phenylbutyrate by using Daucus carota (wild carota) with excellent chemical yield (90%) and ee (99%). [10] However, in this process, a large amount of cells was needed, while this procedure was timeconsuming (10 days). Herein, we first report the enantioselective preparation of ethyl (R)-2-hydroxy-4-phenylbutyrate through bioreduction of ethyl 2-oxophenylbutyrate in pure aqueous medium with high activity and enantioselectivity (yield 92%, 99% ee) by Candida boidinii CIOC21 in a comparatively short time (12 h).…”

Section: Introductionmentioning

confidence: 99%

Preparation the Key Intermediate of Angiotensin‐Converting Enzyme (ACE) Inhibitors: High Enantioselective Production of Ethyl (R)‐2‐Hydroxy‐4‐Phenylbutyrate with Candida boidinii CIOC21

Chen

Lin

et al. 2008

Adv Synth Catal

View full text Add to dashboard Cite

Forty microorganisms belonging to different taxonomical groups were used to catalyze the enantioselective reduction of ethyl 2-oxophenylbutyrate to afford the corresponding ethyl 2-hydroxy-4-phenylbutyrate. Several microorganisms led to over 99% ee of ethyl (S)-2-hydroxy-4-phenylbutyrate. Especially, we firstly found that the Candida boidinii CIOC21 could be effectively used for the enantioselective preparation the ethyl (R)-2-hydroxy-4-phenylbutyrate in pure aqueous medium with 99% ee, a key intermediate in the production of angiotensinconverting enzyme (ACE) inhibitors.

show abstract

Section: Introductionmentioning

confidence: 99%

Preparation the Key Intermediate of Angiotensin‐Converting Enzyme (ACE) Inhibitors: High Enantioselective Production of Ethyl (R)‐2‐Hydroxy‐4‐Phenylbutyrate with Candida boidinii CIOC21

Chen

Lin

et al. 2008

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…Kluyveromyces marxianus, Pichia pastoris, Pichia anomala, and Pichia angusta have also been tested in the asymmetric reduction of OPBE into (R)-HPBE, and P. angusta displayed the best performance of 100% conversion and 81% ee [35]. Besides, Chadha et al reported the preparation of (R)-HPBE from OPBE by using Daucus carota with excellent chemical yield (90%) and ee (99%) [36]. Chen et al investigated the ability of 40 yeasts kept in CIOC (Chinese Institute of Organic Chemistry, Chinese Academy of Sciences) in the reduction of OPBE.…”

Section: Screening Of Microorganisms For Bioreductive Preparation Of mentioning

confidence: 99%

Bioreductive preparation of ACE inhibitors precursor (R)-2-hydroxy-4-phenylbutanoate esters: Recent advances and future perspectives

2015

Bioresour. Bioprocess.

View full text Add to dashboard Cite

Optically active (R)-2-hydroxy-4-phenylbutanoate esters ((R)-HPBE) are key precursors for the production of angiotension-converting enzyme (ACE) inhibitors, which are important prescriptive drugs for preventing the formation of angiotensin II and lowering the blood pressure. The biocatalytic asymmetric reduction of ethyl 2-oxo-4-phenylbutanoate (OPBE) to (R)-HPBE with carbonyl reductases has several advantageous attributes, including high enantioselectivity, mild reaction condition, high catalytic efficiency, and environmental benignity. An increasing number of OPBE reductases have been discovered owing to the drastic achievements in genomics, screening and evolution technologies, and process engineering. The potential of (R)-HPBE production process has also been intensively evaluated. This review covers recent progress on the bioreductive preparation of (R)-HPBE, especially on various screening approaches for the identification of OPBE reductases and their characterization.

show abstract

“…109 The same group had earlier reported on the reduction of 2-oxo-4-phenylbutanoic acid ethyl ester (90) in >99% ee by plant cell cultures of D. carota. 110 The 4-aryl-2-oxobut-3-enoic acid ethyl and methyl esters were substituted by Cl or CH 3 . Each was incubated with the tissue culture cells of D.…”

Section: Chartmentioning

confidence: 99%

Vegetables as Chemical Reagents

et al. 2007

View full text Add to dashboard Cite

Biocatalysis is an important adjunct to the chemical armamentarium that organic chemists may bring to bear for the synthesis of important intermediates and finished pharmaceutical and other commercial products. For most of the world however, such catalytic reagents are not an option due to their high cost and import limitations. Recent studies indicate that the use of locally available vegetables may offer an alternative opportunity for countries to investigate their local resources for the effective conduct of key synthetic transformations with significant economic and ecological implications. This review offers a brief overview of the field of microbial and plant biocatalysts, discusses the studies thus far on the use of intact plant materials for conducting synthetic chemical reactions, and considers some opportunities for future development.

show abstract

Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures

Cited by 45 publications

References 15 publications

Preparation the Key Intermediate of Angiotensin‐Converting Enzyme (ACE) Inhibitors: High Enantioselective Production of Ethyl (R)‐2‐Hydroxy‐4‐Phenylbutyrate with Candida boidinii CIOC21

Preparation the Key Intermediate of Angiotensin‐Converting Enzyme (ACE) Inhibitors: High Enantioselective Production of Ethyl (R)‐2‐Hydroxy‐4‐Phenylbutyrate with Candida boidinii CIOC21

Bioreductive preparation of ACE inhibitors precursor (R)-2-hydroxy-4-phenylbutanoate esters: Recent advances and future perspectives

Vegetables as Chemical Reagents

Contact Info

Product

Resources

About