Understanding the chiral recognitions between neuraminidases and inhibitors: Studies with DFT, docking, and MD methods
Identifieur interne : 000315 ( Istex/Checkpoint ); précédent : 000314; suivant : 000316Understanding the chiral recognitions between neuraminidases and inhibitors: Studies with DFT, docking, and MD methods
Auteurs : Zhiwei Yang [République populaire de Chine] ; Xiaomin Wu [République populaire de Chine] ; Gang Yang [République populaire de Chine] ; Yuangang Zu [République populaire de Chine] ; Lijun Zhou [République populaire de Chine]Source :
- International Journal of Quantum Chemistry [ 0020-7608 ] ; 2012-02-05.
English descriptors
- Teeft :
- Active site, Active sites, Aqueous solutions, Binding mode, Bioactive form, Bl1z, Bl2z, Bl3z, Bl4z, Bl9z, Black lines, Blxz, Blxz stereoisomers, Carboxyl, Carboxyl group, Chem, Chem phys, Chiral, Chiral ligands, Chiral recognitions, Chirality, Color figure, Docking, Einter, Electrostatic contributions, Electrostatic interactions, Hydrophobic, Hydrophobic cave, Information table, Inhibitor, Inhibitors figure, Interaction energies, Interaction energy, International journal, Kcal, Largest interaction energy, Ligand, Neutral form, Neutral forms, Online, Online issue, Oseltamivir, Phys, Phys chem, Propenyl, Propenyl group, Quantum chem, Quantum chemistry, Relative energies, Stereoisomer, Stereoisomers, Zhou, Zwitterionic, Zwitterionic form.
Abstract
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
Url:
DOI: 10.1002/qua.23046
Affiliations:
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wicri:level="1"><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023</wicri:regionArea><wicri:noRegion>Dalian 116023</wicri:noRegion></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Correspondence address: Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040</wicri:regionArea><wicri:noRegion>Harbin 150040</wicri:noRegion></affiliation></author><author><name sortKey="Zu, Yuangang" sort="Zu, Yuangang" uniqKey="Zu Y" first="Yuangang" last="Zu">Yuangang Zu</name><affiliation wicri:level="1"><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 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type="main">International Journal of Quantum Chemistry</title><title level="j" type="alt">INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY</title><idno type="ISSN">0020-7608</idno><idno type="eISSN">1097-461X</idno><imprint><biblScope unit="vol">112</biblScope><biblScope unit="issue">3</biblScope><biblScope unit="page" from="909">909</biblScope><biblScope unit="page" to="921">921</biblScope><biblScope unit="page-count">13</biblScope><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><pubPlace>Hoboken</pubPlace><date type="published" when="2012-02-05">2012-02-05</date></imprint><idno type="ISSN">0020-7608</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0020-7608</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Active site</term><term>Active sites</term><term>Aqueous solutions</term><term>Binding mode</term><term>Bioactive 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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</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Yang, Zhiwei" sort="Yang, Zhiwei" uniqKey="Yang Z" first="Zhiwei" last="Yang">Zhiwei Yang</name></noRegion><name sortKey="Wu, Xiaomin" sort="Wu, Xiaomin" uniqKey="Wu X" first="Xiaomin" last="Wu">Xiaomin Wu</name><name sortKey="Yang, Gang" sort="Yang, Gang" uniqKey="Yang G" first="Gang" last="Yang">Gang Yang</name><name sortKey="Yang, Gang" sort="Yang, Gang" uniqKey="Yang G" first="Gang" last="Yang">Gang Yang</name><name sortKey="Yang, Gang" sort="Yang, Gang" uniqKey="Yang G" first="Gang" last="Yang">Gang Yang</name><name sortKey="Zhou, Lijun" sort="Zhou, Lijun" uniqKey="Zhou L" first="Lijun" last="Zhou">Lijun Zhou</name><name sortKey="Zu, Yuangang" sort="Zu, Yuangang" uniqKey="Zu Y" first="Yuangang" last="Zu">Yuangang Zu</name><name sortKey="Zu, Yuangang" sort="Zu, Yuangang" uniqKey="Zu Y" first="Yuangang" last="Zu">Yuangang Zu</name><name sortKey="Zu, Yuangang" sort="Zu, Yuangang" uniqKey="Zu Y" first="Yuangang" last="Zu">Yuangang Zu</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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