2022
DOI: 10.1021/acsomega.2c02506
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Computational Insights into the Regeneration of Ovothiol and Ergothioneine and Their Selenium Analogues by Glutathione

Abstract: Ovothiol and ergothioneine are powerful antioxidants that readily react with oxidants by forming their respective disulfides. In fact, ovothiol is widely considered one of the most powerful natural antioxidants. However, for these antioxidants to be again involved in reacting with oxidants, they must be regenerated via the reduction of the disulfide bonds. In the present work, the regeneration of the antioxidants ovothiol and ergothioneine and their selenium analogues, by the closed-shell nucleophilic attack o… Show more

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Cited by 3 publications
(1 citation statement)
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“…These compounds occur in three differently methylated forms (A, B, and C) and are characterized by unique redox properties suggestive of numerous cellular functions [14,[16][17][18][19]. They possess unusual antioxidant properties due to the peculiar position of the sulfhydryl group on the imidazole ring of histidine, which confers ovothiols remarkable reactivity towards reactive oxygen species (ROS) [14,[20][21][22]. The pKa of the thiol group of ovothiol A is much lower (~1.4) than that of glutathione (GSH) (~8.7).…”
Section: Introductionmentioning
confidence: 99%
“…These compounds occur in three differently methylated forms (A, B, and C) and are characterized by unique redox properties suggestive of numerous cellular functions [14,[16][17][18][19]. They possess unusual antioxidant properties due to the peculiar position of the sulfhydryl group on the imidazole ring of histidine, which confers ovothiols remarkable reactivity towards reactive oxygen species (ROS) [14,[20][21][22]. The pKa of the thiol group of ovothiol A is much lower (~1.4) than that of glutathione (GSH) (~8.7).…”
Section: Introductionmentioning
confidence: 99%