咪唑类离子液体与酪氨酸相互作用及机理的密度泛函理论研究

doi:10.3866/PKU.WHXB202002021

Abstract

Abstract:

Ionic liquids (ILs) are thermally and chemically stable and have adjustable structures, which gives them the potential to be used as green, efficient biomolecular solvents. Given the critical role of ILs in dissolving biomolecules, the mechanism of interaction between them deserves further study. Herein, density functional theory (DFT) calculations, using the SMD implicit water solvent model, were employed to study the interaction and mechanism between a hydrophobic zwitterionic amino acid (Tyr) and a series of imidazolium ILs with different alkyl chain lengths and methylation sites. The contributions of hydrogen bonding (H-bonding), electrostatic effects, induction, and dispersion to the intermolecular interactions were determined by combining the symmetry-adapted perturbation theory (SAPT), the atoms in molecules (AIM) theory, and reduced density gradient (RDG) analysis. The results indicate that the H-bonding between the IL cation and Tyr is stronger than that between the IL anion and Tyr; however, the binding between either ion and Tyr is dominated by electrostatic effects. By contrast, the difference between the induction and dispersion forces is small when methylation occurs on the C2 site of the imidazolium cation; whereas, it is significantly large when methylation takes place on the N3 site. This is rationalized by the interaction patterns that vary based on the methylation site. H-bonding and π⁺-π stacking interactions between the imidazole and benzene rings are dominant during C2-methylation, while H-bonding and C_Alkyl-H…π interactions between the alkyl chain and benzene ring are dominant during N3-methylation. Increasing the side alkyl chain length has different effects on the interaction energy to cations with different methylation sites. During N3-methylation, when the side alkyl chain length increases from 4 to 12, there are significant van der Waals interactions between the Tyr benzene and the side alkyl chain. However, these van der Waals interactions are inapparent when methylation takes place on the C2 site. Finally, the synergetic effect of the H-bonding and the interaction between the benzene and the side alkyl chain for C2-methylation is greater than the H-bonding and the interaction between the imidazole and benzene rings for N3-methylation, when the side alkyl chain length n > 9. Therefore, the interaction strength and mechanism in these imidazolium-Tyr complexes can be regulated by changing the methylation site and the side alkyl chain length of the cation. Further study of ion-pair and Tyr reveals that the change tendency of the interaction energy of IL-Tyr systems is consistent with that of cation-Tyr cases, and the ion pair further stabilizes the binding with Tyr. These results illustrate the interaction mechanism of IL-Tyr systems and provide a novel strategy for the design and screening of functional ILs for amino acid extraction and separation in the future.

Key words: Ionic liquids, Zwitterionic amino acid, Interaction and mechanism, Hydrogen bond effect, Van der Waals effect

MSC2000:

O641

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Zhiwei Wu, Weilu Ding, Yaqin Zhang, Yanlei Wang, Hongyan He. Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study[J].Acta Phys. -Chim. Sin., 2021, 37(10): 2002021.

Figures/Tables 12

References 47

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R-H	C₄-3mim	C₄-2mim	C₁₂-3mim	C₁₂-2mim
-C2-H	0.271	N/A	0.271	N/A
-N3-H	N/A	0.478	N/A	0.478
-C4-H	0.267	0.267	0.266	0.267
-C5-H	0.267	0.266	0.267	0.266
-CH₃-H1	0.230	0.258	0.230	0.257
-CH₃-H2	0.232	0.260	0.232	0.259
-CH₃-H3	0.235	0.257	0.235	0.257

Complex	H-bond	Distance/nm	Angle/(°)	ΔE_Ion-Tyr/(kJ·mol^-1)
C₄-3mim-Tyr	C2-H…O_COO	0.233	155.0	-44.96
C₄-2mim-Tyr	N3-H…O_COO	0.168	174.7	-57.31
C₁₂-3mim-Tyr	C2-H…O_COO	0.226	151.3	-64.23
	C_Alkyl-H…O_OH	0.270	132.7	N/A
C₁₂-2mim-Tyr	N3-H…O_COO	0.169	168.9	-61.14
BF₄-Tyr	N_Tyr-H…F1	0.252	106.9	-31.75
	N_Tyr-H…F2	0.190	161.8	N/A
	C_Amino-H…F1	0.249	124.6	N/A

Ion-Tyr	H-bond	ρ_BCP/(a.u.)	▽²ρ_BCP/(a.u.)	H_BCP/(10^-3 a.u.)
C₄-3mim-Tyr	C2-H…O_COO	0.011	0.039	1.437
C₄-2mim-Tyr	N3-H…O_COO	0.047	0.137	-5.634
C₁₂-3mim-Tyr	C2-H…O_COO	0.014	0.047	1.626
	C_Alkyl-H…O_OH	0.007	0.021	0.491
C₁₂-2mim-Tyr	N3-H…O_COO	0.045	0.138	-4.675
BF₄-Tyr	N_Tyr-H…F1	N/A	N/A	N/A
	N_Tyr-H…F2	0.023	0.098	2.025
	C_Amino-H…F1	0.008	0.031	1.049

ILs-Tyr	H-bond	ρ_BCP/(a.u.)	▽²ρ_BCP/ (a.u.)	H_BCP/(10^-3 a.u.)
[C₄-3mim][BF₄]-Ty	C2-H…O_COO	0.011	0.035	1.300
	N_Tyr-H…F1	0.011	0.045	1.462
	N_Tyr-H…F1	N/A	N/A	N/A
	N_Tyr-H…F2	0.022	0.093	2.007
[C₄-2mim][BF₄]-Tyr	N3-H…O_COO	0.050	0.141	-7.241
	N_Tyr-H…F1	0.027	0.115	1.922
	C_Ben-H…F2	0.006	0.022	0.867
	C_Ben-H…F3	0.008	0.030	0.995
[C₁₂-3mim][BF₄]-Tyr	C2-H…Ocoo	0.007	0.023	0.556
	C_Alkyl-H…O_OH	0.013	0.043	1.455
	N_Tyr-H…F2	0.022	0.091	2.022
	N_Tyr-H…F1	N/A	N/A	N/A
	N_Tyr-H…F1	N/A	N/A	N/A
	C_Ben-H…F1	0.007	0.028	1.015
[C₁₂-2mim][BF₄]-Tyr	N3-H…O_COO	0.047	0.137	-5.678
	N_Tyr-H…F1	0.024	0.100	1.959
	N_Tyr-H…F2	N/A	N/A	N/A

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Interaction and Mechanism between Imidazolium Ionic Liquids and the Zwitterionic Amino Acid Tyr: a DFT Study

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