Chemo-enzymatic synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate

D’Arrigo, Paola; Pedrocchi-Fantoni, Giuseppe; Servi, Stefano De

doi:10.1016/j.tetasy.2010.05.023

Cited by 17 publications

(7 citation statements)

References 25 publications

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“…The optical rotation of 12b achieved was measured as −13.2 ( c = neat) at 25°C. The reported value of 12b was [α] D 25 = −9.3° ( c = neat; Arrigo et al ., 2010). Much more work is being conducted to scale up the catalytic reaction in a commercial purpose for the chiral compound.…”

Section: Resultsmentioning

confidence: 99%

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Han

Wang

Pei

et al. 2020

Microbial Biotechnology

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Summary Chiral aromatic alcohols have received much attention due to their widespread use in pharmaceutical industries. In the asymmetric synthesis processes, the excellent performance of alcohol dehydrogenase makes it a good choice for biocatalysts. In this study, a novel and robust medium‐chain alcohol dehydrogenase RhADH from Rhodococcus R6 was discovered and used to catalyse the asymmetric reduction of aromatic ketones to chiral aromatic alcohols. The reduction of 2‐hydroxyacetophenone (2‐HAP) to (R)‐(‐)‐1‐phenyl‐1,2‐ethanediol ((R)‐PED) was chosen as a template to evaluate its catalytic activity. A specific activity of 110 U mg−1 and a 99% purity of e.e. was achieved in the presence of NADH. An efficient bienzyme‐coupled catalytic system (RhADH and formate dehydrogenase, CpFDH) was established using a two‐phase strategy (dibutyl phthalate and buffer), which highly raised the tolerated substrate concentration (60 g l−1). Besides, a broad range of aromatic ketones were enantioselectively reduced to the corresponding chiral alcohols by this enzyme system with highly enantioselectivity. This system is of the potential to be applied at a commercial scale.

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Section: Resultsmentioning

confidence: 99%

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Han

Wang

Pei

et al. 2020

Microbial Biotechnology

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“…2010 年 Servi 等 [19] 筛选了一批微生物, 发现 Pichia pastoris 用于 11 的催化还原也有较好的效果. 通过加入吸附性树脂调节原料和产物在溶剂中的浓度, 可以有效地将 (R)-EHPB 的对映选择性提高到 95%.…”

Section: Methodsunclassified

Progress in the Synthesis of Optically Pure Ethyl 2-Hydroxy-4-phenylbutyrate

L黤eng¹,

Chen²,

Meng³

et al. 2012

Chin. J. Org. Chem.

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“…D' Arrigo and coworkers proved that XAD™ 1180, a polystyrenic adsorbent selected among several Amberlite resins, was effective in controlling the OPBE amount presented in water phase. OPBE (1 g L −1 ) could be reduced asymmetrically employing Pichia pastoris with 99% conversion and 95% ee (R) [7]. Continuous batch reactor (CBR) was established combining the biotransformation and OPBE/ HPBE adsorption.…”

Section: Other Processesmentioning

confidence: 99%

“…(R)-2-hydroxy-4-phenylbutanoate esters (OPBE), one class of chiral alcohols, are important precursors for the production of serials of angiotensin-converting enzymes (ACE) inhibitors, generally named as pril drugs (benazepril, cilazapril, quinapril, and ramipril), possessing (S)-homophenylalanine moiety as pharmacophore [5][6][7]. ACE (Kininase II, peptidyldipeptide hydrolase, EC 3.4.15.1) could catalyze the production of vasoconstrictor angiotensin II and inactivation of vasodilator bradykinin.…”

Section: Introductionmentioning

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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Chemo-enzymatic synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate

Cited by 17 publications

References 25 publications

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Green and scalable synthesis of chiral aromatic alcohols through an efficient biocatalytic system

Progress in the Synthesis of Optically Pure Ethyl 2-Hydroxy-4-phenylbutyrate

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

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