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Theoretical study of the reaction of vitamin B6 with 1O2
Örebro University, Department of Natural Sciences. (Biofysikalisk och teoretisk kemi)
Örebro University, Department of Natural Sciences. (Molekylär biokemi)
Örebro University, Department of Natural Sciences. (Molekylär biokemi)ORCID iD: 0000-0003-3315-8835
Örebro University, Department of Natural Sciences. (Biofysikalisk och teoretisk kemi)
2007 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 13, no 16, p. 4636-42Article in journal (Refereed) Published
Abstract [en]

Singlet oxygen is known to cause oxidative stress in cells, leading to severe damage (e.g., lipid peroxidation, membrane degradation, mutagenic alterations to DNA, protein misfunctionality). Recently, pyridoxine has been discovered to be capable of quenching singlet oxygen, however, the mechanism of this reaction remains essentially unknown. In this work, we have investigated four sets of reactions: 1) 1,3-addition to a double bond connected to a hydrogen-carrying group,resulting in the formation of allylic hydroperoxides; 2) [p2+p2] 1,2-cycloaddition to an isolated double bond, resulting in the formation of 1,2-peroxides; 3) 1,4-cycloaddition to a system containing at least two conjugated double bonds, resulting in the formation of the so-called 1,4-peroxides;4) 1,4-addition to phenols and naphthols with the formation of hydroperoxide ketones. Thermodynamically, reaction 4 and the 6(9), 3(8), and 5(8) cases of reaction 1 are the most exergonic ones, with energies ranging from 16 to 18 kcalmol 1. Furthermore, reaction 4 shows the lowest barrier through the reaction path, and is predicted to be the preferred mechanism

for the pyridoxine + singlet-oxygen reaction, which is in agreement with previous experimental results.

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlag , 2007. Vol. 13, no 16, p. 4636-42
Keywords [en]
Computer Simulation, Hydrogen Peroxide/chemical synthesis, Models; Chemical, Molecular Structure, Oxygen/*chemistry, Quantum Theory, Thermodynamics, Vinyl Compounds/chemistry, Vitamin B 6/*chemistry
National Category
Medical Biotechnology (with a focus on Cell Biology (including Stem Cell Biology), Molecular Biology, Microbiology, Biochemistry or Biopharmacy) Natural Sciences Chemical Sciences
Research subject
Biochemistry
Identifiers
URN: urn:nbn:se:oru:diva-4128DOI: 10.1002/chem.200700002PubMedID: 17348056OAI: oai:DiVA.org:oru-4128DiVA, id: diva2:138427
Available from: 2007-11-06 Created: 2007-11-06 Last updated: 2017-12-14Bibliographically approved

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Matxain, Jon MRistilä, MikaelStrid, ÅkeEriksson, Leif A

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Medical Biotechnology (with a focus on Cell Biology (including Stem Cell Biology), Molecular Biology, Microbiology, Biochemistry or Biopharmacy)Natural SciencesChemical Sciences

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