Circular dichroism studies on absolute configuration assignment of peptidomimetics with a terminal chiral 3-arylpropionic acid unit |
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| Affiliation: | 1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland;2. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland;3. Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland;1. School of Materials Science and Engineering, Jiangsu Collaborative Innovation Center of Photovoltaic Science and Engineering, Changzhou University, Changzhou 213164, China;2. College of Chemistry, Key Lab of Environment-Friendly Chemistry and Application of the Ministry of Education, Xiangtan University, Xiangtan 411105, China;3. State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China;1. School of Pharmacy, Department of Medicinal Chemistry, University of Mississippi, University, MS 38677, United States;2. Department of Medicine, San Francisco General Hospital, University of California, San Francisco, CA 94143, United States;3. Schrodinger, Inc., 120 West 45th Street, 17th Floor, New York, NY 10036, United States;4. National Center for Natural Products Research, University of Mississippi, University, MS 38677, United States;5. School of Pharmacy, Department of Pharmaceutical Sciences, Loma Linda University, Loma Linda, CA 92350, United States;1. Laboratoire de Chimie Moléculaire et Thioorganique, CNRS UMR 6507, Normandie University, ENSICAEN & UNICAEN, 6 Bvd du Maréchal Juin, 14050 Caen, France;2. Laboratory of Heteroatom Organic Chemistry, University of Carthage, Faculty of Sciences of Bizerte, 7021 Jarzouna, Tunisia;1. Institute for Eye Cancer, L V Prasad Eye Institute, Hyderabad, India;2. Ophthalmic Pathology Service, L V Prasad Eye Institute, Hyderabad, India |
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| Abstract: | The relationship between the molecular structure of peptidomimetics 1 and their chiroptical properties has been studied using circular dichroism spectroscopy. It was demonstrated that the sign of the Cotton effects occurring around 230 and 270 nm enables the direct assignment of stereochemistry at C-1 and C-3 carbon atoms. The TD-DFT calculations of the circular dichroism (CD) spectrum of one of the model compounds confirm the absolute stereochemistry assignment made experimentally. Thus, CD spectroscopy proved to be a simple, reliable and general tool for the determination of the absolute configuration of the stereogenic centers of peptidomimetics with a terminal 3-arylpropionic group. |
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