Energy barrier determination of enantiomerization of chiral 3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide type compounds by enantioselective stopped-flow HPLC |
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| Affiliation: | 1. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Modena e Reggio Emilia, Via Campi 183, 4100 Modena, Italy;2. Dipartimento di Scienze del Farmaco, Università degli Studi ‘G. d’Annunzio’ Chieti-Pescara, Via dei Vestini, 66100 Chieti, Italy;1. Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Bengkulu, W.R Supratman, Kandang Limun, 38371 A Bengkulu, Indonesia;2. WPI-Advanced Institute of Materials Research, Tohoku University, Sendai 980-8577, Japan;1. Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling, Shaanxi 712100, China;2. Shaanxi Key Laboratory for Catalysis, College of Chemical and Environment Science, Shaanxi University of Technology, Hanzhong, Shaanxi 723001, China;1. Dpto. Biología Animal, Universidad de La Laguna, 38200, La Laguna, Tenerife, Spain;2. Dpto. Física, IUdEA, Universidad de La Laguna, 38200, La Laguna, Tenerife, Spain;3. Instituto de Productos Naturales y Agrobiología, CSIC, 38206, La Laguna, Spain;4. Dpto. Físiología, Universidad de La Laguna, 38200, La Laguna, Tenerife, Spain;5. Dpto. Química Orgánica, Universidad de La Laguna, 38200, La Laguna, Tenerife, Spain;6. Unidad Asociada ULL-CSIC, “Fisiología y Biofísica de la Membrana Celular en Enfermedades Neurodegenetarivas y Tumorales”, 38200, La Laguna, Tenerife, Spain;7. Instituto Universitario de Bioorgánica “Antonio González” Universidad de La Laguna, 38200, La Laguna, Tenerife, Spain |
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| Abstract: | The synthesis and enantioseparation of chiral 3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide derivatives are reported herein. A HPLC stopped-flow procedure was applied to the determination of rate constants and free energy barriers of enantiomerization of the compounds synthesized in the presence of achiral stationary phase. The individual enantiomers of the studied compounds were isolated in parallel by preparative HPLC on a Chiraspher NT column. Rate constants and free energy barriers of enantiomerization were determined in the mobile phase. The results were used to determine the influence of the chiral stationary phase on the enantiomerization process. |
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