Complexation of carboxylate anions with the arginine gas-phase amino acid: Effects of chain length on the geometry of extended ion binding

Luxford, Thomas F. M.; Milner, Edward M.; Yoshikawa, Naruo; Bullivant, Chad; Dessent, Caroline E. H.

doi:10.1016/j.cplett.2013.05.040

Cited by 10 publications

(6 citation statements)

References 34 publications

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“…Resonance excitation amplitudes for thermal decomposition of molecular ions within a quadrupole ion trap have been shown to correlate with literature critical dissociation energies. However, given that is no direct conversion from the resonance excitation voltage to absolute CID energies, such CID energies are therefore quoted as a percentage of the 2.5 V excitation voltage, in line with other standard practices [ 33 , 38 , 39 , 40 ].…”

Section: Methodsmentioning

confidence: 88%

“…Low-energy collision-induced dissociation (CID) was performed to investigate the ground-state thermal fragmentation characteristics of [RF − H] − , using the aforementioned Bruker AmaZon mass spectrometer. Here, an excitation AC folder was applied to the end caps of the ion trap to induce low-energy collisions of the trapped anions with the helium buffer gas, as has been described in detail previously [ 33 , 38 ]. Precursor ion excitation within the quadrupole ion trap occurs through multiple low-energy collisions with helium.…”

Section: Methodsmentioning

confidence: 99%

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Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

2021

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The application of electrospray ionisation mass spectrometry (ESI-MS) as a direct method for detecting reactive intermediates is a technique of developing importance in the routine monitoring of solution-phase reaction pathways. Here, we utilise a novel on-line photolysis ESI-MS approach to detect the photoproducts of riboflavin in aqueous solution under mildly alkaline conditions. Riboflavin is a constituent of many food products, so its breakdown processes are of wide interest. Our on-line photolysis setup allows for solution-phase photolysis to occur within a syringe using UVA LEDs, immediately prior to being introduced into the mass spectrometer via ESI. Gas-phase photofragmentation studies via laser-interfaced mass spectrometry of deprotonated riboflavin, [RF − H]−, the dominant solution-phase species under the conditions of our study, are presented alongside the solution-phase photolysis. The results obtained illustrate the extent to which gas-phase photolysis methods can inform our understanding of the corresponding solution-phase photochemistry. We determine that the solution-phase photofragmentation observed for [RF − H]− closely mirrors the gas-phase photochemistry, with the dominant m/z 241 condensed-phase photoproduct also being observed in gas-phase photodissociation. Further gas-phase photoproducts are observed at m/z 255, 212, and 145. The value of exploring both the gas- and solution-phase photochemistry to characterise photochemical reactions is discussed.

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Section: Methodsmentioning

confidence: 88%

Section: Methodsmentioning

confidence: 99%

Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

2021

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“…A different kind of head to tail dimer is formed in the lysine and arginine dications. Their C 1 structures are oriented so that the protonated side chains interact with the neutral carboxyl groups to form macrocyclic ring structures . These geometries result in the formation of strong hydrogen bonds between charged and neutral centers but are formed at the expense of the electrostatic repulsion since the positively charged centers are closer together than in structures analogous to those for 10 and 11 (i.e., carboxylic acid-like dimers).…”

Section: Resultsmentioning

confidence: 99%

Electrostatically Defying Cation–Cation Clusters: Can Likes Attract in a Low-Polarity Environment?

et al. 2013

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Like-charge ion pairing is commonly observed in protein structures and plays a significant role in biochemical processes. Density functional calculations combined with the conductor-like polarizable continuum model were employed to study the formation possibilities of doubly charged noncovalently linked complexes of a series of model compounds and amino acids in the gas phase and in solution. Hydrogen bond interactions were found to offset the Coulombic repulsion such that cation-cation clusters are minima on the potential energy surfaces and neither counterions nor solvent molecules are needed to hold them together. In the gas phase the dissociation energies are exothermic, and the separation barriers span from 1.7 to 15.6 kcal mol(-1). Liquid-phase computations indicate that the separation enthalpies of the cation-cation complexes become endothermic in water and nonpolar solvents with dielectric constants of ≥7 (i.e., the value for THF). These results reveal that electrostatically defying noncovalent complexes of like-charged ions can overcome their Coulombic repulsion even in low-polarity environments.

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“…Some studies have shown that the species with larger alkyl chains have larger E 1/2 values under CID conditions. 23,38 On the other hand, it has been proposed that the stability of the heterodimeric non-covalent complexes increases when the gas-phase basicity values of the two species that form a complex are similar. 39,40 Thus, the larger is the basicity difference between the zwitterion and 5-methylcytosine the least stable is the complex.…”

Section: Collision-induced Dissociation Of the Ion-zwitterion Complexesmentioning

confidence: 99%

“…It has often been described by collisioninduced dissociation (CID) and subsequent determination of half-dissociation threshold energies 22,23 (E 1/2 ). The plots of these energies vs. alkyl chain length could be compared to the plots of K a vs. alkyl chain length.…”

Section: Introductionmentioning

confidence: 99%

Electrospray Ionization Mass Spectrometry of Non-Covalent Complexes Formed between N-Alkylimidazolium-Containing Zwitterionic Sulfonates and Protonated Bases

Podjava

Kistkin

Ausekle

et al. 2014

Eur J Mass Spectrom (Chichester)

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This paper describes non-covalent complexes between zwitterionic 3-(1-alkyl-3N-imidazolio)-propane-1-sulfonates and different amines. Electrospray ionization (ESI) mass spectrometry and collision-induced dissociation were used to measure the stability of such complexes in solution and in the gas phase. Generally, zwitterionic sulfonates formed more abundant complexes with protonated 5-methylcytosine (5-MCH) than with aliphatic amines. The results show that the association constants and half-dissociation threshold energies of these complexes nonlinearly depend on the alkyl chain length of the zwitterion. It is shown that the complexes with the lowest stability exist in acetonitrile solution or in the gas phase. The factors responsible for this complicated behavior are discussed.The structure of the complexes was investigated by quantum chemical calculations using molecular mechanics and density functional theory. Hydrogen bonding is proposed as the main type of interaction responsible for the stability of ion-zwitterion complexes. In summary, the information obtained in this study could be used for the development of the new derivatization reagents for some compounds containing amidinium groups, like 5-MCH, to increase selectivity of ESI-based methods.

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Complexation of carboxylate anions with the arginine gas-phase amino acid: Effects of chain length on the geometry of extended ion binding

Cited by 10 publications

References 34 publications

Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

Photodegradation of Riboflavin under Alkaline Conditions: What Can Gas-Phase Photolysis Tell Us about What Happens in Solution?

Electrostatically Defying Cation–Cation Clusters: Can Likes Attract in a Low-Polarity Environment?

Electrospray Ionization Mass Spectrometry of Non-Covalent Complexes Formed between N-Alkylimidazolium-Containing Zwitterionic Sulfonates and Protonated Bases

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