Mechanistic insights into the water-catalysed ring-opening reaction of vitamin E by means of double-hybrid density functional theory

Farzaneh Sarrami, Asja A. Kroeger, Amir Karton

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The potent antioxidant α-tocopherol is known to trap two hydroxyl radicals leading to the formation of the experimentally observed α-tocopherylquinone product. Based on double-hybrid density functional theory calculations, we propose for the first time, a reaction mechanism for the conversion of α-tocopherol to α-tocopherylquinone. We find that a water-catalysed ring-opening reaction plays a key role in this conversion. The water catalysts act as proton shuttles facilitating the proton transfers and reducing the ring strain in the cyclic transition structures. On the basis of the proposed reaction mechanism, we proceed to design an antioxidant with potentially enhanced antioxidant properties.

Original languageEnglish
Pages (from-to)123-129
Number of pages7
JournalChemical Physics Letters
Volume708
DOIs
Publication statusPublished - 16 Sep 2018

Fingerprint

tocopherol
antioxidants
Vitamin E
Density functional theory
Tocopherols
Antioxidants
density functional theory
Water
rings
water
Proton transfer
protons
hydroxyl radicals
Hydroxyl Radical
Protons
traps
catalysts
Catalysts
products
tocopherylquinone

Cite this

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title = "Mechanistic insights into the water-catalysed ring-opening reaction of vitamin E by means of double-hybrid density functional theory",
abstract = "The potent antioxidant α-tocopherol is known to trap two hydroxyl radicals leading to the formation of the experimentally observed α-tocopherylquinone product. Based on double-hybrid density functional theory calculations, we propose for the first time, a reaction mechanism for the conversion of α-tocopherol to α-tocopherylquinone. We find that a water-catalysed ring-opening reaction plays a key role in this conversion. The water catalysts act as proton shuttles facilitating the proton transfers and reducing the ring strain in the cyclic transition structures. On the basis of the proposed reaction mechanism, we proceed to design an antioxidant with potentially enhanced antioxidant properties.",
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Mechanistic insights into the water-catalysed ring-opening reaction of vitamin E by means of double-hybrid density functional theory. / Sarrami, Farzaneh; Kroeger, Asja A.; Karton, Amir.

In: Chemical Physics Letters, Vol. 708, 16.09.2018, p. 123-129.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Mechanistic insights into the water-catalysed ring-opening reaction of vitamin E by means of double-hybrid density functional theory

AU - Sarrami, Farzaneh

AU - Kroeger, Asja A.

AU - Karton, Amir

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Y1 - 2018/9/16

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AB - The potent antioxidant α-tocopherol is known to trap two hydroxyl radicals leading to the formation of the experimentally observed α-tocopherylquinone product. Based on double-hybrid density functional theory calculations, we propose for the first time, a reaction mechanism for the conversion of α-tocopherol to α-tocopherylquinone. We find that a water-catalysed ring-opening reaction plays a key role in this conversion. The water catalysts act as proton shuttles facilitating the proton transfers and reducing the ring strain in the cyclic transition structures. On the basis of the proposed reaction mechanism, we proceed to design an antioxidant with potentially enhanced antioxidant properties.

KW - Density functional theory

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