Efficient regioselective acylation of andrographolide catalyzed by immobilized Burkholderia cepacia lipase |
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| Affiliation: | 1. College of Food Science &Technology, Nanjing Agricultural University, Nanjing 210095, PR China;2. Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Damanhour University, Damanhour, Egypt;2. Department of Pharmaceutical Chemistry, Almaarefa Colleges for Science and Technology, Riyadh 11597, Saudi Arabia;3. Department of Organic Chemistry, College of Pharmacy, Misr University for Science and Technology, 6th of the October, PO Box 77, Egypt;1. Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Medicinal Chemistry & Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;3. Center for NMR & Structural Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;1. J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, v.v.i., Dolejškova 3, CZ-182 23 Prague 8, Czech Republic;2. L.V. Pisarzhevskiy Institute of Physical Chemistry, National Academy of Sciences of Ukraine, pr. Nauky, 31, Kyiv 03028, Ukraine;3. Instituto Universitario de Tecnología Química CSIC-UPV and Departamento de Química, Universidad Politécnica de Valencia, Av. De los Naranjos s/n, 46022 Valencia, Spain;1. Department of Fine Chemical Engineering, Hanyang University ERICA, 55 Hanyangdaehak-ro Sangnok-gu, Ansan, Gyunggi-do 426-791, Republic of Korea;2. Research Center for Environment Resource & Processes, Korea Research Institute of Chemical Technology, 141 Gajeong-ro, Yuseong-gu, Daejeon 305-600, Republic of Korea |
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| Abstract: | For the first time, PSL-C, an immobilized lipase from Burkholderia cepacia, was successfully applied to the regioselective acylation of andrographolide by vinyl acetate in acetone. FT-IR spectra demonstrated the occurrence of acylation reaction. The 13C NMR, ESI-MS and elemental analysis confirmed that the 14-acetylandrographolide was formed exclusively. Water activity and reaction temperature had a significant effect on the initial rate and the substrate conversion, but little effect on the regioselectivity of the reaction. The optimal water activity and reaction temperature were 0.11 and 50 °C, respectively. Under these conditions, the initial rate and substrate conversion were 50.2 mM h−1 and 99.0%, respectively, after a reaction time of around 4 h. Besides, immobilized lipase also displayed higher operational stability and 83.5% of its original activity was maintained after being reused for eight batches. |
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