Redox turnover of organometallic B12 cofactors recycles vitamin C: Sulfur assisted reduction of dehydroascorbic acid by cob(II)alamin

Dereven’kov, Ilia А.; Hannibal, Luciana; Dürr, Maximilian; Salnikov, Denis S.; Bui, Thu Thuy; Макаров, С. В.; Койфман, О. И.

doi:10.1016/j.jorganchem.2017.01.002

Cited by 15 publications

(9 citation statements)

References 37 publications

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“…The most likely reason for the rapid increase in k′ with increasing pH is that deprotonation of GSH to give GS – (p K a = 8.9 at 25 °C) occurs, and GS – binds more rapidly to Cbi(II) compared with GSH. A similar pH dependence was previously observed for the reactions between Cbl(II) and DHA in the presence of GSH, cysteine, or acetylcysteine …”

Section: Resultssupporting

confidence: 83%

“…Next, we studied the reaction of Cbi(II) with DHA in the presence of GSH. A direct interaction between Cbi(II) and DHA does not occur, as is the case with the reaction of DHA and Cbl(II) . UV/Vis spectra of the interaction of Cbi(II) with DHA in the presence of GSH (Figure S13) indicate a reversibility of the process: the UV/Vis spectrum of the product formed during the course of the first step shows an absorption band at 500–560 nm similar to that of GS – –Cbi(III), which is partially reduced to Cbi(II) during the second step (Figure S13).…”

Section: Resultsmentioning

confidence: 95%

“…This behavior can be explained by an increase in concentration of the GS – –Co II complex, which was previously proved to be involved in the DHA reduction. [14a] The complexation of thiols on Cbi(II) was earlier shown using EPR spectroscopy . We also observed the GSH binding by Co II during a titration of Cbi(II) with GSH at pH 6.7 (i.e.…”

Section: Resultsmentioning

confidence: 99%

“…O 2 – , NO, NO 2 , ClO 2 , SO 2 –[10] , and others) and strong oxidants (ONOOH, HOCl, and others), but modestly reactive (or unreactive) toward many other reactants . We found that Cbl(II) reduces dehydroascorbic acid to ascorbic acid in the presence of biological ligands – GSH,[14a] thiocyanate,[14a] cysteine, and acetylcysteine;[14b] thiols and thiocyanate being the catalysts of the reaction between Cbl(II) and DHA.…”

Section: Introductionmentioning

confidence: 98%

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Studies on the Reduction of Dehydroascorbic Acid by Glutathione in the Presence of Aquahydroxocobinamide

et al. 2018

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This study reports that aquahydroxocobinamide [(H 2 O)(HO -)Cbi(III)], a nucleotide-free analogue of cobalamin (vitamin B 12 ; Cbl), is capable of catalyzing the reduction of the two-electron oxidized form of vitamin C, dehydroascorbic acid (DHA), to ascorbic acid by glutathione (GSH), whereas catalytic quantities of aquacobalamin do not accelerate the reaction. This observation is explained by different reactions taking place [a]

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Section: Resultssupporting

confidence: 83%

Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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Studies on the Reduction of Dehydroascorbic Acid by Glutathione in the Presence of Aquahydroxocobinamide

et al. 2018

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“…GSCbl reacts at a high rate with nitric oxide to give nitroxylcobalamin . Thiolato–Cbls(III) are products of reactions between Cbl(II) and dehydroascorbic acid in the presence of GSH, Cys, or acetylcysteine …”

Section: Introductionmentioning

confidence: 99%

Kinetic and Mechanistic Studies on the Reaction between Aquacobalamin and Selenocysteine

2017

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We studied the reaction between aquacobalamin (H2OCbl) and selenocysteine (Sec), a selenium‐containing analogue of cysteine, using conventional UV/Vis spectroscopy. This reaction leads to the formation of cob(II)alamin [Cbl(II)] without any detectable intermediate complexation of Cbl(III) with selenocysteine, whereas the interaction between H2OCbl and cysteine proceeds distinctly through the coordination of Cys onto the CoIII ion with further reduction of the CoIII–Cys complex to Cbl(II). The latter is slower than the reaction with Sec. We also showed that selenocystine is capable of accelerating the reduction of H2OCbl to Cbl(II) by cysteine.

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Can Particulate Matter and Nano Metal Oxide Particles Affect the Redox Cycling of Nitrosylcobalamin in Weakly Acidic Aqueous Solution?

2021

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Since air pollution is one of the most serious environmental problems, the study of the effects of particulate matter (PM) on physiological processes remains to be an important challenge for scientific communities. The presented studies form part of the project 'Air Pollution versus Autoimmunity: Role of multiphase aqueous Inorganic Chemistry'. In these studies we examined the effect of Standard Reference Material 1648a, supplied by the US National Institute of Standards and Technology (NIST), and its inorganic constituents on the formation of nitrosylcobalamin (CblNO) in the reaction between nitrocobalamin (CblNO 2 ) and ascorbic acid in a weakly acidic medium. We monitored the reaction in the presence of urban NIST PM (SRM 1648a), plasma treated NIST PM (LAP) and a number of metal oxide nanoparticles, including redox active metal oxides. The obtained results clearly demonstrated that the presence of these different nanoparticles affected the rate of formation of CblNO but did not affect the nature of the final product. Special attention was given to systematic studies on the role of inorganic nanoparticles as a part of the selected PM in the reaction between CblNO 2 and ascorbic acid.

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Redox turnover of organometallic B12 cofactors recycles vitamin C: Sulfur assisted reduction of dehydroascorbic acid by cob(II)alamin

Cited by 15 publications

References 37 publications

Studies on the Reduction of Dehydroascorbic Acid by Glutathione in the Presence of Aquahydroxocobinamide

Studies on the Reduction of Dehydroascorbic Acid by Glutathione in the Presence of Aquahydroxocobinamide

Kinetic and Mechanistic Studies on the Reaction between Aquacobalamin and Selenocysteine

Can Particulate Matter and Nano Metal Oxide Particles Affect the Redox Cycling of Nitrosylcobalamin in Weakly Acidic Aqueous Solution?

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