57646-32-9Relevant academic research and scientific papers
A Novel esterase from Pseudochrobactrum asaccharolyticum WZZ003: Enzymatic properties toward model substrate and catalytic performance in chiral fungicide intermediate synthesis
Cheng, Feng,Cheng, Feifei,Zheng, Jianyong,Wu, Guanzhong,Zhang, Yinjun,Wang, Zhao
, p. 92 - 98 (2018)
Only a few esterases have been used for the synthesis of optically pure fungicide. For example, (R)-metalaxyl synthesized using esterase-involved bioreaction displays fungicide activity, whereas (S)-enantiomer is redundant. However, the biosynthesis of (R
Enzyme-catalyzed preparation of methyl (R)-N-(2,6-dimethylphenyl)alaninate: A key intermediate for (R)-metalaxyl
Park, Oh-Jin,Lee, Sang-Hyun,Park, Tae-Yoon,Lee, Sang-Who,Cho, Koon-Ho
, p. 1221 - 1225 (2007/10/03)
A biocatalytic approach for the production of (R)-metalaxyl, mefenoxam, has been developed. A practical synthesis of methyl (R)-N-(2,6-dimethylphenyl) alaninate, a key intermediate for (R)-metalaxyl, has been developed by the use of lipase-catalyzed hydrolytic kinetic resolution and chemical racemization of the remaining ester. At high concentrations in aqueous media (300 g/L) lipases were stable and gave moderate to good conversions and excellent enantioselectivities (>98% ee). A simple extraction procedure was used to separate the acid product from the remaining ester and the acid was esterified with methanol to give methyl (R)-N-(2,6-dimethylphenyl)alaninate without any reduction in enantiomeric excess (>98% ee). Subsequent chemical coupling with methoxyacetyl chloride provided enantiomerically pure (R)-metalaxyl (>98% ee) without racemization.
