Electron Capture Dissociation of Disulfide, Sulfur–Selenium, and Diselenide Bound Peptides

Li, Huilin; O’Connor, Peter B.

doi:10.1007/s13361-012-0473-0

Cited by 11 publications

(18 citation statements)

References 41 publications

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“…In odd‐electron based tandem mass spectrometry methods such as ECD, ETD, and EDD, it has been widely observed that the disulfide bond is readily cleaved (Zubarev et al, ; Chrisman et al, ; Kalli & Håkansson, ; Wu et al, ; Cole et al, ; Li & O'Connor, ). Likewise, in radical‐based tandem mass spectrometry, disulfide bonds are selectively cleaved (Lee et al, ; Tan & Xia, ).…”

Section: Fragmentation Characterisitcsmentioning

confidence: 99%

Radical‐driven peptide backbone dissociation tandem mass spectrometry

Moon

2014

Mass Spectrometry Reviews

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In recent years, a number of novel tandem mass spectrometry approaches utilizing radical-driven peptide gas-phase fragmentation chemistry have been developed. These approaches show a peptide fragmentation pattern quite different from that of collision-induced dissociation (CID). The peptide fragmentation features of these approaches share some in common with electron capture dissociation (ECD) or electron transfer dissociation (ETD) without the use of sophisticated equipment such as a Fourier-transform mass spectrometer. For example, Siu and coworkers showed that CID of transition metal (ligand)-peptide ternary complexes led to the formation of peptide radical ions through dissociative electron transfer (Chu et al., 2000. J Phys Chem B 104:3393-3397). The subsequent collisional activation of the generated radical ions resulted in a number of characteristic product ions, including a, c, x, z-type fragments and notable side-chain losses. Another example is the free radical initiated peptide sequencing (FRIPS) approach, in which Porter et al. and Beauchamp et al. independently introduced a free radical initiator to the primary amine group of the lysine side chain or N-terminus of peptides (Masterson et al., 2004. J Am Chem Soc 126:720-721; Hodyss et al., 2005 J Am Chem Soc 127: 12436-12437). Photodetachment of gaseous multiply charged peptide anions (Joly et al., 2008. J Am Chem Soc 130:13832-13833) and UV photodissociation of photolabile radical precursors including a C-I bond (Ly & Julian, 2008. J Am Chem Soc 130:351-358; Ly & Julian, 2009. J Am Soc Mass Spectrom 20:1148-1158) also provide another route to generate radical ions. In this review, we provide a brief summary of recent results obtained through the radical-driven peptide backbone dissociation tandem mass spectrometry approach.

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Section: Fragmentation Characterisitcsmentioning

confidence: 99%

Radical‐driven peptide backbone dissociation tandem mass spectrometry

Moon

2014

Mass Spectrometry Reviews

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“…Directly below sulfur in the periodic table is selenium. Sulfur and selenium are known to have similar physical and chemical properties [27][28][29]. Although there are similarities between sulfur and selenium, their antioxidant mechanisms differ in preventing oxidative cellular damage [4,30].…”

Section: Introductionmentioning

confidence: 99%

A Computational Investigation of the Binding of the Selenium Analogues of Ergothioneine and Ovothiol to Cu(I) and Cu(II) and the Effect of Binding on the Redox Potential of the Cu(II)/Cu(I) Redox Couple

Wiebe

Zaliskyy

Bushnell

2019

Journal of Chemistry

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The complexes formed from the binding of ovoselenol (OSeH) and ergoseloneine (ESeH) to Cu(II) and Cu(I) have been investigated with DFT methods. From the calculated thermodynamics, the binding of OSeH and ESeH to Cu(II) and Cu(I) ions increases the reduction potential for the Cu(II)/Cu(I) redox couple. The calculated reduction potentials for the Cu(II)(OSe)2/Cu(I)(OSeH)3+ and Cu(II)(ESe)2/Cu(I)(ESeH)3+ redox couples were found to be 1.15 V and 1.24 V in a dilute aqueous solution. By combining the half reactions for the oxidation of OSeH to the diselenide OSeSeO with the reduction of Cu(II)(OSe)2 to Cu(I)(OSeH)3+, the calculated EMF was 0.90 V. For the oxidation of ESeH to the diselenide ESeSeE with the concomitant reduction of Cu(II)(ESe)2 to Cu(I)(ESeH)3+, the calculated EMF was 0.67 V. Thus, for both systems, the reduction of Cu(II) to Cu(I) with concomitant formation of either diselenide is thermodynamically favourable, and it is expected that both OSeH and ESeH are suitable for the protection against copper induced oxidative damage. As a result, the inhibition of the recycling of Cu(I) to Cu(II) is thermodynamically favourable in the presence of OSeH and ESeH.

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“…The typical symbol for such anionic systems is (RX.˙.XR) •‐ in which X denotes S, Se, N, P, and so on and R denotes Ph, CH 3 , and other functional groups . Electron capture dissociation (ECD) with Fourier transform ion cyclotron mass spectrometry (FTICR MS) has been used for direct measurement of sulfur and selenium centered 2c‐3e bond complexes …”

Section: Introductionmentioning

confidence: 99%

“…Optical absorption spectra, and in particular the position of λ max and lifetimes ( t 1/2 ) of these bands may be used to provide indirect information on the nature and strength of 2c‐3e bonds of these complexes. Characterization of 2c‐3e bond in cyclic dithia radical cations, pepetides, azoalkanes, transition metal complexes, and other sigma bonded radical cationic complexes through optical absorption spectroscopy are reported in the literature. Absorption maximum ( λ max ) is described to correspond the energy gap between the doubly occupied σ bonding orbital and singly occupied σ* antibonding orbital and this is often being correlated to the strength of a 2c‐3e ‐S∴S‐ bond.…”

Section: Introductionmentioning

confidence: 99%

Effect of excess electron on structure, bonding, and spectral properties of sulfur/selenium based dichalcogen systems

Kumar

Maity

2018

Int J of Quantum Chemistry

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First principle based quantum chemical methods are employed to characterize structure, bonding, and spectral properties of sulfur and selenium based dichalcogen systems in presence of an excess electron. Inter molecular two-center three-electron (2c-3e) bonding between two chalcogen (X) atoms is described in the systems of the type (R-X) 2•-(R = Ph, PhCH 2 X = S, Se). In addition, effect of electron withdrawing (-NO 2 ) and electron donating (-CH 3 ) groups in phenyl ring on the stability of these 2c-3e bonded systems is also studied in water medium applying a macroscopic hydration model. Molecular parameters and binding energy of the neutral, (R-X) 2 and reduced, (R-X) 2 •dichalcogen systems are compared. Search for minimum energy structures of these open shell doublet systems are carried out applying various density functionals with dispersion corrections and MP2 method considering 6-311++G (d,p) set of basis functions for all atoms. Effect of water medium is introduced through a macroscopic solvation model based on density (SMD). Frontier molecular orbitals based analysis is carried out for showing the definite presence of 2c-3e bond between two chalcogen atoms in these radical anions of sulfur and selenium based aromatic dichalcogen systems. Excited state calculations are performed on all these systems using Time Dependent Density Functional Theory (TDDFT). UV-Vis spectra are simulated and effect of solvent water on the absorption maximum of these radical anions is discussed. This study illustrates that the combination of electronic effect and geometrical flexibility decides the strength of two-center three-electron bond in these systems. K E Y W O R D S 2c-3e bond, antioxidant, chalcogen, density functional theory, excess electron, hemi bond, radical anion, selenium, sulfur 1 | INTRODUCTIONSulfur and selenium are present in amino acids, peptides, and proteins, essential for various biological redox reactions. Selenocystine and selenomethonine systems can act as an antioxidant by killing harmful peroxides in organisms, and these are also responsible for protection against inflammation and cancer. [1][2][3] Sulfur and selenium based diaryl dichalcogenes are eco-friendly oxidizing agents and demanding drugs in pharmaceutical chemistry mainly for their antioxidant properties. [4] One electron reduction of neutral disulfides and diselenides may lead to the formation of two-center three-electron (2c-3e) bonded radical anion systems. [5][6][7][8][9][10][11][12][13] The extra electron in such systems is accommodated in the lowest unoccupied molecular orbital which is often an antibonding sigma orbital. Due to the presence of this electron in a repulsive antibonding orbital, such three electron bonded species are not very stable and may dissociate easily. Having two electrons in the highest bonding sigma orbital and one electron in the lowest antibonding sigma orbital results in the formation of a half bond (bond order = 0.5) and hence these 2c-3e bond is also known as hemi bond or half bond. The typical symbol for s...

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Electron Capture Dissociation of Disulfide, Sulfur–Selenium, and Diselenide Bound Peptides

Cited by 11 publications

References 41 publications

Radical‐driven peptide backbone dissociation tandem mass spectrometry

Radical‐driven peptide backbone dissociation tandem mass spectrometry

A Computational Investigation of the Binding of the Selenium Analogues of Ergothioneine and Ovothiol to Cu(I) and Cu(II) and the Effect of Binding on the Redox Potential of the Cu(II)/Cu(I) Redox Couple

Effect of excess electron on structure, bonding, and spectral properties of sulfur/selenium based dichalcogen systems

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