Enzymatic desymmetrization of cis-1,3-cyclohexanedicarboxylic acid diesters |
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| Affiliation: | 1. Universidade Federal do Paraná, Departamento de Química, Centro Politécnico, Curitiba 81.531-980, Brazil;2. Universidade Federal do Paraná, Departamento de Bioquímica e Biologia Molecular, Centro Politécnico, Curitiba 81.531-980, Brazil;1. School of Pharmaceutical Sciences, Nanjing Tech University, No.30 South Puzhu Road, Pukou District, 211816, Nanjing, PR China;2. College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, No.30 South Puzhu Road, Pukou District, 211816, Nanjing, PR China;3. College of Food Science and Light Industry, Nanjing Tech University, No.30 South Puzhu Road, Pukou District, 211816, Nanjing, PR China;4. Jiangsu National Synergetic Innovation Center for Advanced Materials, 30 Puzhunan Road, Nanjing 211816, Jiangsu, PR China;1. Federal University of Ceará, Department of Organic and Inorganic Chemistry, Laboratory of Biotechnology and Organic Synthesis (LABS), Campus do Pici, Postal Box 6044, 60455-970, Fortaleza, Ceará, Brazil;2. Laboratory SPCMIB UMR 5068, CNRS, Paul Sabatier – Toulouse III University, 118 Route de Narbonne, 31062, Toulouse Cedex 9, France;3. LCC-CNRS, Université de Toulouse, CNRS, Toulouse, France;4. LCC-CNRS, Université de Toulouse, CNRS, Université Toulouse 3-Paul Sabatier, Toulouse, France;1. The Department of Neurochemistry, Palladin Institute of Biochemistry, NAS of Ukraine, 9 Leontovicha Street, Kiev 01601, Ukraine;2. The Department of Fine Organic Synthesis, Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine, Murmanskaya Street. 1, Kiev 02094, Ukraine;3. Organic Chemistry Institute, Corrensstr. 40, D-48149 Münster, Germany |
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| Abstract: | cis-1,3-Cyclohexanedicarboxylic acid (1,3-CHDA) monoesters were prepared in high overall yield and high enantiomeric purity using a three step process from cis/trans-1,3-CHDA. The asymmetry is induced by an enzymatic hydrolytic desymmetrization of a meso cis-1,3-CHDA diester. A judicious choice of ester substituents and enzyme can provide >80% overall yield of either enantiomer in >94% ee. |
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