The species-specific acid-base and multinuclear magnetic resonance properties of selenocysteamine, selenocysteine, and their homodiselenides

Pálla, Tamás; Mirzahosseini, Arash; Noszál, Béla

doi:10.1016/j.cplett.2019.137076

Cited by 6 publications

(6 citation statements)

References 15 publications

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“…In Figure 2, sample NMR spectra are presented that were obtained for cysteamine at basic pH. e limiting chemical shifts of all studied compounds were determined analogously followed by the calculation of species-specific chemical shifts using Sudmeier-Reilley equations [27]; this determination method was recently formulated for the similar selenocysteine/selenocystine pair [28]. e species-specific chemical shifts are assembled in Tables 1 and 2, for the reduced and oxidized forms of the compounds, respectively.…”

Section: Resultsmentioning

confidence: 99%

Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine

Santana

Mirzahosseini

Noszál

2022

Journal of Spectroscopy

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1H and 13C NMR measurements were carried out to explore anticipated correlations between chemical shifts versus thiolate basicities and redox potentials of cysteamine, homocysteine, penicillamine, and their homodisulfides. All correlations were analyzed and statistically evaluated. The closest correlation was observed for the αCH nuclei concerning 1H and 13C NMR data. Since neither site-specific basicities nor site-specific redox potentials can be directly measured by any means in peptides and proteins containing several thiol and/or disulfide units, these data provide a simple method and predictive power to estimate the aforementioned site-specific physicochemical parameters for analogous sulfur-containing moieties in related biopolymers.

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Section: Resultsmentioning

confidence: 99%

Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine

Santana

Mirzahosseini

Noszál

2022

Journal of Spectroscopy

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“…Although significant differences can be observed, 1 H NMR chemical shift values of the SeH group are typically comprised in the range δ H À 0.95 ppm (aliphatic selenols) and δ H 1.80 ppm (aromatic selenols). [28,32,57,[68][69][70][71]…”

Section: Other Methodologies For the Synthesis Of Aromatic Selenolsmentioning

confidence: 99%

Synthesis and Applications of Organic Selenols

Tanini

Capperucci

2021

Adv Synth Catal

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The synthesis and the study of organoselenium compounds have received much attention over the past decades. Selenium-containing organic molecules are widely used in organic synthesis, materials science, and medicinal chemistry. Selenium -and more specifically the amino acid selenocysteine, bearing a selenol (SeH) moiety -is present in at least 25 human protein families, whose biological functions have not been completely identified. Amongst the variety of organoselenium compounds, selenols are a versatile class of molecules easily undergoing a broad array of useful transformations. Because of the unique properties of the SeH group, selenol chemistry has important applications in chemical sciences, spanning from organic synthesis to materials chemistry and biology. This review summarises currently available methodologies for the synthesis of selenols and highlights applications of selenols in chemical sciences and biology. Conclusions and Outlook 5.1. Safety Measures

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“…Dithiotreitol is highly driven towards its oxidized, ring-closing form [ 47 , 50 ]. The reaction between diselenides and DTT can be reasonably treated in terms of K C , a cumulative equilibrium constant.…”

Section: Selenolate-diselenide and Thiolate-disulfide Redox Equilibri...mentioning

confidence: 99%

“…This method requires the knowledge of species-specific protonation constants, including those of the minor microspecies; otherwise, redox processes could only be characterized at the level of phenomena. The complete set of the microscopic protonation constants of the studied selenium-containing compounds (CysASeH, CysSeH) has recently been published [ 50 ].…”

Section: The Role Of Ph In the Selenolate-diselenide And Thiolate-dis...mentioning

confidence: 99%

Properties of Selenolate-Diselenide Redox Equilibria in View of Their Thiolate-Disulfide Counterparts

2023

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Selenium, the multifaceted redox agent, is characterized in terms of oxidation states, with emphasis on selenol and diselenide in proteinogenic compounds. Selenocysteine, selenocystine, selenocysteamine, and selenocystamine are depicted in view of their co-dependent, interfering acid-base, and redox properties. The pH-dependent, apparent (conditional), and pH-independent, highly specific, microscopic forms of the redox equilibrium constants are described. Experimental techniques and evaluation methods for the determination of the equilibrium and redox parameters are discussed, with a focus on nuclear magnetic resonance spectroscopy, which is the prime technique to observe selenium properties in organic compounds. The correlation between redox, acid-base, and NMR parameters is shown in diagrams and tables. The fairly accessible NMR and acid-base parameters are discussed to assess the predictive power of these methods to estimate the site-specific redox properties of selenium-containing moieties in large molecules.

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The species-specific acid-base and multinuclear magnetic resonance properties of selenocysteamine, selenocysteine, and their homodiselenides

Cited by 6 publications

References 15 publications

Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine

Correlation between the NMR Chemical Shifts and Thiolate Protonation Constants of Cysteamine, Homocysteine, and Penicillamine

Synthesis and Applications of Organic Selenols

Properties of Selenolate-Diselenide Redox Equilibria in View of Their Thiolate-Disulfide Counterparts

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