Lipase-catalyzed kinetic resolution of 2-aminocyclopentane- and 2-aminocyclohexanecarboxamides |
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| Affiliation: | 1. Department of Pharmacology, Drug Development and Therapeutics/Laboratory of Synthetic Drug Chemistry and Department of Chemistry, University of Turku, Lemminkäisenkatu 5 C, FIN-20520 Turku, Finland;2. Institute of Pharmaceutical Chemistry, University of Szeged, PO Box 427, H-6701 Szeged, Hungary;1. Academy of Scientific and Innovative Research, CSIR-Indian Institute of Integrative Medicine, Jammu 180 001, India;2. Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180 001, India;1. Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588-0304, USA;2. Department of Nutrition and Health Sciences, University of Nebraska-Lincoln, Lincoln, NE 68583-0806, USA;1. Medicinal Chemistry Division, Indian Institute of Integrative Medicine (IIIM), Jammu, Jammu and Kashmir 180001, India;2. Academy of Scientific and Innovative Research (AcSIR), 2-Rafi Marg, New Delhi, India;1. Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, IL 60208, United States;2. Department of Pharmacology, Northwestern University, Chicago, IL 60611, United States;3. Robert H. Lurie Comprehensive Cancer Center, Feinberg School of Medicine, Northwestern University, Chicago, IL 60611, United States |
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| Abstract: | Candida antarctica lipase B (CAL-B)-catalyzed N-acylation with 2,2,2-trifluoroethyl butanoate in solvent mixtures of tert-butyl methyl ether and tert-amyl alcohol was used to prepare all the enantiomers of cis- and trans-2-aminocyclopentane- and -cyclohexanecarboxamides. An unexpected change in enantiopreference, accompanied by low enantioselectivity, was observed when Pseudomonas cepacia lipase (cis-cyclohexane substrate) or C. antarctica lipase A (cis-cyclopentane and -cyclohexane substrates) replaced CAL-B. |
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