Proceedings of the National Academy of Sciences | VOL. 119
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Proton-coupled electron transfer of macrocyclic ring hydrogenation: The chlorinphlorin

Publication Date May 9, 2022

Abstract

Significance The chemical reduction of unsaturated bonds occurs by hydrogenation with H 2 as the reductant. Conversely, in biology, the unavailability of H 2 engenders the typical reduction of unsaturated bonds with electrons and protons from different cofactors, requiring olefin hydrogenation to occur by proton-coupled electron transfer (PCET). Moreover, the redox noninnocence of tetrapyrrole macrocycles furnishes unusual PCET intermediates, including the phlorin, which is an intermediate in tetrapyrrole ring reductions. Whereas the phlorin of a porphyrin is well established, the phlorin of a chlorin is enigmatic. By controlling the PCET reactivity of a chlorin, including the use of a hangman functionality to manage the proton transfer, the formation of a chlorinphlorin by PCET is realized, and the mechanism for its formation is defined.

Concepts

Proton-coupled Electron Transfer Reduction Of Bonds Proton-coupled Electron Transfer Reactivity Redox Noninnocence Tetrapyrrole Ring Tetrapyrrole Macrocycles Ring Reductions Ring Hydrogenation Macrocyclic Ring Olefin Hydrogenation

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No potential conflict of interest was reported by the authors. The conception and design of the study, acquisition of data, analysis and interpretatio...

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