Infrared and 1H NMR structural study of 3-tropane, 3-granatane and 3-bicyclo(3.2.1)octane epimeric amino acids |
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| Affiliation: | 1. The Key Laboratory of Industrial Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu 214122, China;2. Center for Synthetic Biochemistry, Institute of Synthetic Biology, Institutes of Advanced Technologies, Shenzhen, China;1. Department of Basic and Applied Chemistry, Faculty of Science and Technology, University of Central Punjab, Lahore 54590, Pakistan;2. INEOS Oxford Institute for Antimicrobial Research and Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, United Kingdom;3. Department of Pharmaceutical Sciences, College of Pharmacy, Al Ain University, Al Ain, P.O. Box 64141, United Arab Emirates;4. AAU Health and Biomedical Research Center, Al Ain University, Abu Dhabi, P.O. Box 144534, United Arab Emirates;5. Chemistry Department, College of Science, King Khalid University, Abha 61421, Saudi Arabia;6. Department of Chemistry and Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester M1 7DN, United Kingdom;2. Berzelii Center EXSELENT, The Arrhenius Laboratory, Stockholm University, Stockholm, Sweden;3. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China |
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| Abstract: | Five amino acids with known configuration: α- and β-3-amino-tropane- and 3-amino-bicyclo(3.2.1)octane-3-carboxylic acids and α -3-amino-granatane-3-carboxylic acid have been studied by i.r. and 1H NMR spectroscopy. Both α- and γ-zwitterion structures have been found for tropane and granatane amino acids. Equatorial and axial ammonium groups in α-zwitterions can be distinguished by the number and frequencies of the ammonium deformation modes. A chair—boat conformation has been deduced for α-3-amino-granatane-3-carboxylic acid. |
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