Understanding the chiral recognitions between neuraminidases and inhibitors: Studies with DFT, docking, and MD methods
Zhiwei Yang
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Search for more papers by this authorXiaomin Wu
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Search for more papers by this authorCorresponding Author
Gang Yang
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, People's Republic of China
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of ChinaSearch for more papers by this authorCorresponding Author
Yuangang Zu
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of ChinaSearch for more papers by this authorLijun Zhou
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Search for more papers by this authorZhiwei Yang
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Search for more papers by this authorXiaomin Wu
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Search for more papers by this authorCorresponding Author
Gang Yang
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, People's Republic of China
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of ChinaSearch for more papers by this authorCorresponding Author
Yuangang Zu
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of ChinaSearch for more papers by this authorLijun Zhou
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, People's Republic of China
Search for more papers by this authorAbstract
The chiral recognitions between various neuraminidases (NA) and 5-[(1R,2S)-1-(acetylamino)-2- methoxy-2-methylpentyl]-4-[(1Z)-1-propenyl)-(4S,5R)]-D-proline (BL) stereoisomers have been theoretically studied. The zwitterions of BL are responsible for the bioactivities, and electrostatic rather than van der Waals (vdW) contributions play a significant role. With the presence of NA proteins, the orders of relative stabilities of the BL stereoisomers are greatly altered; meanwhile, the ranges are significantly enlarged, ensuring the respective recognitions of the BL9z, BL3z, BL2z, and BL1z stereoisomers by the N1, N2, N9 subtype, and B type NA proteins. It is mainly due to geometric complementarities of the NA active sites with the BL carboxyl and propenyl groups. The recognitions of proteins with chiral ligands are rather targeted, even applicable to N2 and N9 with high structural similarities. Thus, the significance of chirality is addressed for the designs of anti-influenza drugs, which aids our understanding of chiral recognitions between proteins and ligands. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem, 2011
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