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

Chen, Yongzheng; Lin, Hui; Xu, Xiao‐Ying; Xia, Shiwen; Wang, Lixin

doi:10.1002/adsc.200700420

Cited by 42 publications

(10 citation statements)

References 31 publications

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“…However, the best result was obtained when aqueous medium without any cosolvents was used, in which the substrate existed as droplets. Similar result was observed in the microbial reduction of ethyl 2-oxo-4-phenylbutyrate [32]. The water-based bioreduction made this procedure more environmentally compatible, and it would contribute to the green and sustainable development of chemical syntheses.…”

Section: Effect Of Cosolvents On the Bioreductionsupporting

confidence: 85%

Integration of newly isolated biocatalyst and resin-based in situ product removal technique for the asymmetric synthesis of (R)-methyl mandelate

Guo

2009

Bioprocess Biosyst Eng

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The enantioselective reduction of methyl benzoylformate to (R)-methyl mandelate, an important pharmaceutical intermediate and a versatile resolving agent, was investigated in this study. After minimizing the reaction-specific constraints (constraints dependent on the nature of the substrate and product) by preliminary selection of the reaction parameters, an effective whole cell biocatalyst (Saccharomyces cerevisiae AS2.1392) was obtained by simple screening procedures. Under further optimized conditions, a product concentration of 103 mmol L(-1) could be attained within 5 h with a yield of 85.8% and an enantiometric excess of 95.4%, indicating S. cerevisiae AS2.1392 an efficient biocatalyst for the asymmetric synthesis of (R)-methyl mandelate. Furthermore, resin-based in situ product removal (ISPR) technique was applied to alleviate the substrate and product inhibition or toxicity to the whole cells. The integration of newly isolated biocatalyst and proper ISPR technique provides a practical route for the preparation of optically active pharmaceutical intermediates.

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Section: Effect Of Cosolvents On the Bioreductionsupporting

confidence: 85%

Integration of newly isolated biocatalyst and resin-based in situ product removal technique for the asymmetric synthesis of (R)-methyl mandelate

Guo

2009

Bioprocess Biosyst Eng

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“…Most of the candidate yeasts shown good (S)-preference (>99%), while Candida boidinii CIOC21 was proved to be (R)-preference. As much as 2.0 g L −1 OPBE could be asymmetrically reduced into (R)-HPBE with 99.7% ee and 95.1% yield [37]. Target reaction oriented enrichment and screening of microorganisms have also been carried out in our laboratory, and one yeast strain Candida krusei SW2026 displayed desirable ee (99.7%) and yield (95.1%) in aqueous phase at 2.5 g L −1 of OPBE [17].…”

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.

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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.

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“…10 -12 Besides, strain screening is also an important tool to obtain desired biocatalysts for the preparation of useful chemicals. 13,14 Optically active alpha-hydroxy acids are key intermediates in the synthesis of pharmaceuticals and fine chemicals. 15 (R)-Mandelic acid, the most important representative of alpha-hydroxy acids, is not only an essential building block for drugs such as semi-synthetic penicillins, 16 cephalosporins, 17 antitumor 18 and anti-obesity agents, 19 but also a versatile resolving agent in chiral resolution processes.…”

Section: Introductionmentioning

confidence: 99%

A highly stable whole‐cell biocatalyst for the enantioselective synthesis of optically active alpha‐hydroxy acids

Guo

Zheng

et al. 2009

J of Chemical Tech & Biotech

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BACKGROUND: Biocatalysts have gained increasing attention because of their inherent advantages over chemical catalysts. However, the poor operational stability has always prevented their broad application. In this study, (R)-mandelic acid was chosen as a model compound of alpha-hydroxy acids. The objective was to obtain a new biocatalyst with desired operational stability for the preparation of (R)-mandelic acid as well as other optically pure alpha-hydroxy acids of pharmaceutical importance.

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

Cited by 42 publications

References 31 publications

Integration of newly isolated biocatalyst and resin-based in situ product removal technique for the asymmetric synthesis of (R)-methyl mandelate

Integration of newly isolated biocatalyst and resin-based in situ product removal technique for the asymmetric synthesis of (R)-methyl mandelate

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

A highly stable whole‐cell biocatalyst for the enantioselective synthesis of optically active alpha‐hydroxy acids

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