Quantum chemical studies on the role of water microsolvation in interactions between group 12 metal species (Hg2+, Cd2+, and Zn2+) and neutral and deprotonated cysteines

Mori, Susumu; Endoh, Tatsuo; Yaguchi, Yuichi; Shimizu, Yuuhei; Kishi, Takayoshi; Yanai, Tetsuya

doi:10.1007/s00214-011-0975-z

Cited by 7 publications

(8 citation statements)

References 85 publications

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“…This is similar to the results of Mori et al who find this [N,CO,S À ]tgg structure as the ground state conformer for [(H 2 O)M(Cys-H)] + where M = Zn 2+ (gas phase and in solution) and Cd 2+ (gas phase). 9 As seen in Fig 2+ . Deprotonation at N is much less favorable with [N À ,CO,S]tggg calculated to be 104-114 kJ mol À1 higher in 298 K free energy for both metals.…”

Section: Theoretical Resultsmentioning

confidence: 70%

“…This is similar to the results of Mori et al who find this [N,CO,S À ]tgg structure as the ground state conformer for [(H 2 O)M(Cys-H)] + where M = Zn 2+ (gas phase and in solution) and Cd 2+ (gas phase). 9 As seen in Fig. 1 for [Zn(Cys-H)] + [N,CO,S À ]tgg, the metal is bound to the amino nitrogen, carbonyl oxygen, and sulfur with bond distances of 2.139, 2.141, and 2.215 Å, respectively.…”

Section: Theoretical Resultsmentioning

confidence: 99%

“…Theoretical investigations by Russo et al of the interactions of cysteine with Cu 2+ , Zn 2+ , Cd 2+ , and Hg 2+ found that zinc and cadmium both form stable complexes by coordination of the metal to cysteine in a tridentate binding pattern involving the amino nitrogen, carbonyl oxygen, and side-chain sulfur. 8 Similarly, quantum chemical studies by Mori et al 9 examined the interactions of Hg 2+ , Cd 2+ , and Zn 2+ with deprotonated cysteine either microsolvated by one or two water molecules or using a polarized continuum model. For one water ligand, they found a similar tridentate motif, where deprotonation occurs at the thiol.…”

Section: Introductionmentioning

confidence: 99%

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Structural characterization of gas-phase cysteine and cysteine methyl ester complexes with zinc and cadmium dications by infrared multiple photon dissociation spectroscopy

Coates

McNary

Boles

et al. 2015

Phys. Chem. Chem. Phys.

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Section: Theoretical Resultsmentioning

confidence: 70%

“…This is similar to the results of Mori et al who find this [N,CO,S À ]tgg structure as the ground state conformer for [(H 2 O)M(Cys-H)] + where M = Zn 2+ (gas phase and in solution) and Cd 2+ (gas phase). 9 As seen in Fig. 1 for [Zn(Cys-H)] + [N,CO,S À ]tgg, the metal is bound to the amino nitrogen, carbonyl oxygen, and sulfur with bond distances of 2.139, 2.141, and 2.215 Å, respectively.…”

Section: Theoretical Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Structural characterization of gas-phase cysteine and cysteine methyl ester complexes with zinc and cadmium dications by infrared multiple photon dissociation spectroscopy

Coates

McNary

Boles

et al. 2015

Phys. Chem. Chem. Phys.

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show abstract

“…To understand the peptide radical cation formation process mediated by reduction of Hg 2+ , we considered the structure of the mercury–peptide complex. According to ab initio calculation of the interaction between Hg 2+ and cysteine, Hg 2+ is coordinated with the thiolate group (−S – ) to form a complex . Notably, the natural charge of mercury in the complex with the lowest energy conformation is only +0.79e .…”

Section: Resultsmentioning

confidence: 99%

Electron Transfer Dissociation Mass Spectrometry of Peptides Containing Free Cysteine Using Group XII Metals as a Charge Carrier

Asakawa

Wada

2014

J. Phys. Chem. B

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Electron transfer dissociation (ETD) has been used for peptide sequencing. Since ETD preferentially produces the c'/z(•) fragment pair, peptide sequencing is generally performed by interpretation of mass differences between series of consecutive c' and z(•) ions. However, the presence of free cysteine residues in a precursor promotes peptide bond cleavage, hindering interpretation of the ETD spectrum. In the present study, the divalent group XII metals, such as Zn(2+), Cd(2+) and Hg(2+), were used as charge carriers to produce metal-peptide complexes. The thiol group is deprotonated by complexation with the group XII metal. The formation of b and y' ions was successfully suppressed by using the zinc-peptide complex as a precursor, indicating Zn(2+)-aided ETD to be a useful method for sequencing of cysteine-containing peptides. By contrast, ETD of Cd(2+)- and Hg(2+)-peptide complexes mainly led to SH2 loss and radical cation formation, respectively. These processes were mediated by recombination energy between the metal cation and an electron. The presence of monovalent cadmium and neutral mercury in ETD products was confirmed by MS(3) analysis with collision-induced dissociation.

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“…Computational studies have been performed to understand the structural and thermodynamics of cysteine‐mercury complex formation. Mori et al used density functional theory (DFT) calculations to understand 1:1 complexes of cysteine to Hg(II) and highlight the importance of the carboxylate group of cysteine in stabilizing the complex whereby a bond between the deprotonated cysteine sulfur and Hg(II) is formed . Gas‐phase DFT studies of neutral cysteine with Hg(II) ions also indicate the importance of carbonyl oxygen atoms in stabilizing the complex .…”

Section: Introductionmentioning

confidence: 99%

Theoretical studies of complexes between Hg(II) ions andl-cysteinate amino acids

Watts

Howell

Merle

2013

Int. J. Quantum Chem.

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In this study, ab initio and density functional theory methods have been used to understand the structures and thermodynamic stabilities of complexes formed between L-cysteine and mercury (II) ions in neutral aqueous solution. To better understand the interaction between sulfur and mercury (II) ion, the MP2, B3LYP, M06-2X, and TPSS methods have been used to optimize [HgSH x ] 22x , x5 1-4, complexes and compared to benchmark QCISD(T) structures. Furthermore, energies from these same methods are compared to CCSD(T)/CBS(2,3) energies. From these benchmark calculations, the M06-2X method was selected to optimize L-cysteinate-Hg(II) complexes and the MP2 method for estimating complex energies. L-cysteinate-mercury (II) ion complexes are formed primarily by forming a bond between cysteinate sulfur and the mercury ion. Stable complexes of L-cysteinate and mercury can be formed in 1:1, 2:1, 3:1, and 4:1 ratios. Each complex is stabilized further by interaction between carboxylate oxygen and mercury as well as hydrogen bonding among complex cysteinate ligands. The results indicate that at high cysteinate to Hg(II) ratios high-coordinate complexes can be present but at lower ratios the 2:1 complex should be dominant.

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Quantum chemical studies on the role of water microsolvation in interactions between group 12 metal species (Hg2+, Cd2+, and Zn2+) and neutral and deprotonated cysteines

Cited by 7 publications

References 85 publications

Structural characterization of gas-phase cysteine and cysteine methyl ester complexes with zinc and cadmium dications by infrared multiple photon dissociation spectroscopy

Structural characterization of gas-phase cysteine and cysteine methyl ester complexes with zinc and cadmium dications by infrared multiple photon dissociation spectroscopy

Electron Transfer Dissociation Mass Spectrometry of Peptides Containing Free Cysteine Using Group XII Metals as a Charge Carrier

Theoretical studies of complexes between Hg(II) ions andl-cysteinate amino acids

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