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Resolution of non-protein amino acids via Carica papaya lipase-catalyzed enantioselective transesterification
Affiliation:1. Department of Chemistry, Faculty of Science and Engineering, Konan University, Higashinada-ku, Kobe 658-8501, Japan;2. Department of Chemical Engineering, National Chen Kung University, Tainan 70101, Taiwan;1. Institute of Chemistry—Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam;2. Equipe Produits Naturels, Synthèses et Chimie Médicinale (PNSCM), UMR CNRS 6226—Institut des Sciences Chimiques de Rennes, Université de Rennes 1, UFR Sciences Pharmaceutiques et Biologiques, 2, Avenue du Prof L. Bernard, F-35043 Rennes Cedex, France;1. Department of Neurology, The First Affiliated Hospital, Sun Yat-Sen University, Guangzhou, Guangdong Province, China;2. Institute of Clinical Pharmacology, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, Guangdong Province, China;1. Department of Ecosystem Analysis, Institute for Environmental Research, ABBt – Aachen Biology and Biotechnology, RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany;2. Man-Technology-Environment Research Centre, School of Science and Technology, Örebro University, Fakultetsgatan 1, 701 82 Örebro, Sweden;1. Departamento de Química Orgánica and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias, Universidad de Alicante, 03080, Alicante, Spain;2. Instituto de Síntesis Orgánica, Facultad de Ciencias, Universidad de Alicante, 03080, Alicante, Spain
Abstract:Carica papaya lipase-catalyzed transesterification of the 2,2,2-trifluoroethyl esters of N-benzyloxycarbonylated dl-amino acids carrying aliphatic side chains proceeded smoothly and, in almost all the cases, enantiospecifically (E = >200), affording the l-methyl esters and leaving the d-trifluoroethyl esters intact.
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