Enzymatic synthesis of N-10-undecenoyl-phenylalanine catalysed by aminoacylases from Streptomyces ambofaciens |
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| Affiliation: | 1. LRGP, UMR 7274 CNRS-Université de Lorraine, 2 avenue de la Forêt de Haye, TSA 40602, F-54518, VANDŒUVRE Cedex, France;2. R&D laboratory of Seppic, Air Liquide Healthcare Specialty Ingredients, 50 boulevard National - CS 90020, 92257, La Garenne Colombes Cedex, France;1. Department of Biochemistry and Clinical Laboratory, Faculty of Medicine, Tabriz University of Medical Sciences, Tabriz, Iran;2. Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran;3. Student Research Committee and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran;1. Department of Radiology, the First Affiliated Hospital of Jinzhou Medical University, Jinzhou 121001, China;2. Department of Stomatology, the First Affiliated Hospital of Jinzhou Medical University, Jinzhou 121001, China;1. Department of Second Gynecology, Cangzhou Central Hospital, Cangzhou, Hebei Province, 061001, China;2. Department of Obstetrics, Dezhou Women and Children’s Hospital, No. 835 Dongdizhong Street, Dezhou City, Shandong, 253000, China;3. Department of Obstetrics, Taian City Central Hospital, Taian, Shandong Province, 271000, China;4. School of Bioprocess Engineering, Universiti Malaysia Perlis, 02600, Arau, Malaysia;5. Institute of Nano Electronic Engineering, Universiti Malaysia Perlis, 01000, Kangar Perlis, Malaysia;6. Department of Obstetrics and Gynecology, Jinan Maternal & Child Care Health Hospital, No. 2, Jian Guo Xiao Jing 3 Road, Jinan, Shandong Province, 250001, China;1. Lorraine University, Laboratory of Biomolecules Engineering (LIBio), 2 Avenue de la Forêt de Haye, TSA40602, F-54518 Vandœuvre-lès-Nancy, France;2. Lorraine University, Laboratory of Reactions and Process Engineering (LRGP-CNRS UMR 7274), 2 Avenue de la Forêt de Haye, TSA40602, F-54518 Vandœuvre-lès-Nancy, France;1. Department of Translational Medicine & Research, SRM Medical College, SRMIST, Tamil Nadu, 603203, India;2. Department of Medical Microbiology, Faculty of Medicine, University of Malaya, Kuala Lumpur, 50603, Malaysia;3. Institute of Craniofacial, Aesthetic & Plastic Surgery (ICAPS), SRM Institute for Medical Sciences (SIMS), Tamil Nadu, 600026, India;4. Nanotechnology Research Center, SRMIST, Tamil Nadu, 603203, India;5. Department of Pharmacology, Saveetha Dental College (SDC), Saveetha Institute of Medical and Technical Sciences, Chennai, Tamil Nadu, India;1. Department of Emergency, China-Japan Union Hospital of Jilin University, Changchun 130033, China;2. Department of Respiratory Medicine, China-Japan Union Hospital of Jilin University, Changchun 130033, China |
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| Abstract: | Due to its physico-chemical and biological activities, N-10-undecenoyl-phenylalanine (C11’F) is one of the most interesting lipoaminoacids used in cosmetic and pharmaceutical industries. Its production is currently based on the Schotten-Baumann chemical reaction, which shows some environmental issues in terms of effluents. As a possible biocatalytic alternative, this study presents the evaluation of the reactional and process conditions allowing the production of C11’F using aminoacylases from Streptomyces ambofaciens culture. These aminoacylases showed the best activity at 45 °C and pH between 7 and 8 with a moderate thermal stability. The influence of substrates concentrations on the kinetic parameters of C11’F synthesis showed a more important impact of the phenylalanine concentration as compared to the 10-undecenoic acid concentration. As a reactional product, C11’F appeared to have an inhibitory effect on the enzymatic N-acylation. Cobalt addition allowed an eleven-fold increase of the reaction rate. Batch reactors were used with free aminoacylases without impact on the final C11’F concentration. For the first time, enzymatically produced C11’F was finally purified at the gram scale as a 99% purity white powder. The evaluation of the biological activity on melanocytes cultures showed the presence of skin lightening activity similar to the one obtained with the chemically produced C11’F. |
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