Prebiotic synthesis of dihydrouridine by photoreduction of uridine in formamide

Xu, Jianfeng; Janicki, Mikołaj J.; Szabla, Rafał; Sutherland, John D.

doi:10.1039/d4cc01823k

Chem. Commun.

2024

DOI: 10.1039/d4cc01823k

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Prebiotic synthesis of dihydrouridine by photoreduction of uridine in formamide

Jianfeng Xu,

Mikołaj J. Janicki,

Rafał Szabla

et al.

Abstract: UV irradiation of mixtures of canonical ribonucleosides (C, U, A, G) leads to a mixture of dihydrouridine (DHU, modified nucleoside in tRNA) with all four RNA canonical nucleosides (C, U, A, G).

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Cited by 2 publications

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Chalcogen Bonds Enable Efficient Photoreduction of Sulfur‐Containing Heterocycles

Janicki,

Szabla

2024

Angewandte Chemie

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Chalcogen bonding interactions have attracted significant attention in a broad chemistry community, with a particular focus on their ability to stabilise the key transition states in various organic synthetic routes. In this work, we demonstrate that they can also be harnessed in selective photoredox reactions, which cannot be otherwise achieved with alternative approaches to photoreduction. We demonstrate this concept through the photoreduction of the sulfur‐containing DNA nucleoside precursor thioanhydrouridine to 2'‐deoxy‐thiouridine, revealing the previously unrecognized role of bisulfide in this process. Based on quantum chemical simulations, we identify a stable chalcogen‐bonding complex of the hydrosulfide anion and thionhydrouridine (HS‐…S contacts), which enables directional photoinduced electron transfer, resulting in the formation of non‐canonical DNA nucleoside. We also disprove the possibility that photoreduction of thioanhydronucleosides could be initiated by hydrated electrons generated from irradiated bisulfide anions which do not interact with the chromophore. Finally, we show that selective photoreduction mediated by chalcogen bonds can only occur for chromophores, which exhibit sufficiently long excited‐state lifetimes in the locally‐excited states to undergo transition to the productive charge transfer state. These findings can be further used in the design of similar photoredox reactions which can employ the potential of chalcogen bonding interactions.

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Chalcogen Bonds Enable Efficient Photoreduction of Sulfur‐Containing Heterocycles

Janicki,

Szabla

2024

Angewandte Chemie

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Chalcogen Bonds Enable Efficient Photoreduction of Sulfur‐Containing Heterocycles

Janicki,

Szabla

2024

Angew Chem Int Ed

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Prebiotic synthesis of dihydrouridine by photoreduction of uridine in formamide

Abstract: UV irradiation of mixtures of canonical ribonucleosides (C, U, A, G) leads to a mixture of dihydrouridine (DHU, modified nucleoside in tRNA) with all four RNA canonical nucleosides (C, U, A, G).

Cited by 2 publications

References 26 publications

Chalcogen Bonds Enable Efficient Photoreduction of Sulfur‐Containing Heterocycles

Chalcogen Bonds Enable Efficient Photoreduction of Sulfur‐Containing Heterocycles

Chalcogen Bonds Enable Efficient Photoreduction of Sulfur‐Containing Heterocycles

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