Synthesis of enantiopure azetidine 2-carboxylic acids and their incorporation into peptides |
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| Institution: | 1. School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210023, China;2. MaAnShan High-Tech Research Institute of Nanjing University, MaAnShan, 238200, China;3. Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain;4. IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain;1. Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Murmanskaya St., 5, UA-02094, Kyiv, Ukraine;2. Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska Str. Kyiv, 01601, Ukraine;3. The Chemours Company, 200 Powder Mill Rd., Experimental Station Wilmington, DE, 19803, USA;1. Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL 60612, United States;2. National Institute of Mental Health Psychoactive Drug Screening Program, Department of Pharmacology and Division of Chemical Biology and Medicinal Chemistry, University of North Carolina Chapel Hill Medical School, Chapel Hill, NC 27599, United States;1. Grupo de Investigación en Química Orgánica y Biomédica, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, A.A. 1890 Barranquilla, Colombia;2. Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, A.A. 1890 Barranquilla, Colombia;3. Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, CIETUS, IBSAL Campus Unamuno, s/n, 37007 Salamanca, Spain;4. Laboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguara, km 2 vía refugio, Piedecuesta A.A. 681011, Colombia |
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| Abstract: | Enantiopure azetidine 2-carboxylic acids were prepared by hydrolysis of the corresponding 2-cyano azetidines, without ring cleavage of the azetidine or epimerization. The produced amino acids, which are conformationally constrained analogues of phenylalanine, can be cleanly debenzylated and used for the synthesis of tripeptides. In the course of the synthesis of new enantiopure 2-cyano azetidines through intramolecular alkylation of a metallated amino nitrile, it was found that the involved anionic cyclisation can be thermodynamically controlled, thus enhancing its diastereoselectivity. |
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