Theoretical study of the scavenging mechanism to 1,4-dicarbonyls by pyridoxamine: The water-assisted reaction |
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| Authors: | Xin Chen Qing-An Qiao Yue-Qing Jin Jie Jing Quan-Wen Liu Li-Xiang Sun Mei-Shan Wang Chuan-Lu Yang |
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| Institution: | aSchool of Chemistry and Materials Science, Ludong University, Yantai 264025, China;bLibrary of Ludong University, Yantai 264025, China;cCollege of Physics and Electronic Engineering, Ludong University, Yantai 264025, China |
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| Abstract: | A theoretical study for the water-assisted scavenging mechanism of pyridoxamine with 1,4-dicarbonyls was investigated by density functional theory (DFT) method at B3LYP/6-31G(d) basis set. Two scavenging pathways were examined: imine formation vs. pyrrole ring formation. In addition, solvent effect was performed using the Onsager model. Our calculations indicated that the pyrrole ring formation was the preferred pathway for the reaction, which results were consistent with experimental data. The participation of one water molecule in the reaction would reduce the active energy considerably and the energy barriers of all the transition states in the water-assisted reaction were much lower than those of the non-assisted reaction. The presence of a solvent in the continuum model disfavors the reaction. Hydrogen-bonding interactions and steric hindrance effect play an important role in the scavenging reaction. |
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| Keywords: | Pyridoxamine Reactive carbonyl compounds Water-assisted mechanism DFT Solvent effect |
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