Optimization of a process for the production of (R)-2-hydroxy-4-phenylbutyric acid — an intermediate for inhibitors of angiotensin converting enzyme
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An improved process for the preparation of ethyl-(R)-2-hydroxy-4-phenylbutyrate, (R)-HPB ester by lipase from Thermomyces lanuginosus
2022, Bioresource Technology ReportsCitation Excerpt :Enantiomerically pure ethyl-(R)-2-hydroxy-4-phenylbutyrate, ((R)-HPB ester, (R)-1) is an essential building block for the production of angiotensin-converting enzyme (ACE) inhibitors (Sheldon et al., 1991) (Fig. 1) e.g. Benazepril (I), Lisinopril (II), Spirapril (III), Enalapril (IV), Quinapril (V), Delapril (VI), Ramipril (VII), Cilazapril (VIII) etc., and numerous methods have been developed for its preparation. These include: a) chemical resolution (Nohira and Yoshida, 1989) (b) asymmetric reduction of its prochiral precursor 2-oxo-4-phenylbutyric acid or its ethyl ester by chemical reagents (Herold et al., 2000; Blaser and Jalett, 1993) or enzymes (Schmidt et al., 1992a; Dao et al., 1998; Schmidt et al., 1992b; Fadnavis and Radhika, 2004) (c) enantioselective enzymatic hydrolysis of cyanohydrin prepared from hydrocinnamaldehyde (Neidermeyer et al., 1991; Osprian et al., 2004; Fadnavis et al., 2004) and esters of 2-hydroxy-4-arylbutyrate (Huang and Tsai, 2004; Sugai and Ohta, 1991; Palomo et al., 2003; Kalaritis et al., 1990; Liese et al., 2002; Ou and Li, 2012; Bastida et al., 1998). Further, an enzymatic approach using lactonase for selective hydrolysis of cis- and trans-2-hydroxy-4-phenyl-4-butyrolactones has also been reported (Chen et al., 2010).
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2019, Comprehensive BiotechnologyRedesigning Cofactor Availability: An Essential Requirement for Metabolic Engineering
2017, Current Developments in Biotechnology and Bioengineering: Functional Genomics and Metabolic EngineeringEnzymatic synthesis of chiral 2-hydroxy carboxylic acids
2015, Process Biochemistry7.10 Reduction: Asymmetric Biocatalytic Reduction of Ketones
2012, Comprehensive Chirality