Journal of Biological Inorganic Chemistry, volume 26, issue 4, pages 427-434

Mechanism of cyanocobalamin chlorination by hypochlorous acid.

Osokin Vladimir S 1
2
 
Laboratory of Clinical Biochemistry and Metabolism, Department of General Pediatrics, Adolescent Medicine and Neonatology, Faculty of Medicine, Medical Center-University of Freiburg, Freiburg, Germany
Publication typeJournal Article
Publication date2021-04-29
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor3
ISSN09498257, 14321327
Biochemistry
Inorganic Chemistry
Abstract
Hypochlorous acid (HOCl) is a strong oxidant produced by myeloperoxidase. Previous work suggested that HOCl modifies the corrin ring of cobalamins to yield chlorinated species via mechanisms that are incompletely understood. Herein, we report a mechanistic study on the reaction between cyanocobalamin (CNCbl, vitamin B12) and HOCl. Under weakly acidic, neutral and weakly alkaline conditions, the reaction produces the c-lactone derivative of CNCbl chlorinated at the C10-position of corrin ring (C10–Cl–CNCbl-c-lactone). Formation of C10–Cl–CNCbl-c-lactone was not observed at pH ≥ 9.9. The chlorination of CNCbl by HOCl proceeds via two pathways involving one and two HOCl molecules: the reaction is initiated by the very fast formation of a complex between CNCbl and HOCl, which either undergoes slow transformation to chlorinated species, or rapidly reacts with a second HOCl molecule to produce C10–Cl–CNCbl. Subsequent reaction of C10–Cl–CNCbl with HOCl proceeds rapidly toward lactone ring formation by H-atom abstraction at position C8. This work uncovered mechanisms and products of the reaction of a biologically active and therapeutically used cobalamin, CNCbl and the endogenous oxidant HOCl. Binding and reactivity studies of C10–Cl–CNCbl and C10–Cl–CNCbl-c-lactone with relevant proteins of the cobalamin pathway and with cultured cells are necessary to elucidate the potential physiological effects of these species.

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Derevenkov I. A. et al. Mechanism of cyanocobalamin chlorination by hypochlorous acid. // Journal of Biological Inorganic Chemistry. 2021. Vol. 26. No. 4. pp. 427-434.
GOST all authors (up to 50) Copy
Derevenkov I. A., Osokin V. S., Hannibal L., Makarov S. V., Khodov I. A., Koifman O. I. Mechanism of cyanocobalamin chlorination by hypochlorous acid. // Journal of Biological Inorganic Chemistry. 2021. Vol. 26. No. 4. pp. 427-434.
RIS |
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TY - JOUR
DO - 10.1007/s00775-021-01869-5
UR - https://doi.org/10.1007%2Fs00775-021-01869-5
TI - Mechanism of cyanocobalamin chlorination by hypochlorous acid.
T2 - Journal of Biological Inorganic Chemistry
AU - Derevenkov, Ilia A
AU - Osokin, Vladimir S
AU - Hannibal, Luciana
AU - Khodov, Ilya A.
AU - Koifman, Oskar I.
AU - Makarov, Sergei V
PY - 2021
DA - 2021/04/29 00:00:00
PB - Springer Nature
SP - 427-434
IS - 4
VL - 26
SN - 0949-8257
SN - 1432-1327
ER -
BibTex |
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BibTex Copy
@article{2021_Derevenkov
author = {Ilia A Derevenkov and Vladimir S Osokin and Luciana Hannibal and Ilya A. Khodov and Oskar I. Koifman and Sergei V Makarov},
title = {Mechanism of cyanocobalamin chlorination by hypochlorous acid.},
journal = {Journal of Biological Inorganic Chemistry},
year = {2021},
volume = {26},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007%2Fs00775-021-01869-5},
number = {4},
pages = {427--434},
doi = {10.1007/s00775-021-01869-5}
}
MLA
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Derevenkov, Ilia A., et al. “Mechanism of cyanocobalamin chlorination by hypochlorous acid..” Journal of Biological Inorganic Chemistry, vol. 26, no. 4, Apr. 2021, pp. 427-434. https://doi.org/10.1007%2Fs00775-021-01869-5.
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