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A Platform for the Synthesis of Oxidation Products of Bilirubin

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MUJAWAR Taufiqueahmed Pirsaheb SEVELDA Petr MADEA Dominik KLÁN Petr ŠVENDA Jakub

Rok publikování 2024
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of the American Chemical Society
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www https://pubs.acs.org/doi/10.1021/jacs.3c11778
Doi http://dx.doi.org/10.1021/jacs.3c11778
Klíčová slova Alkyls; Cross coupling reaction; Organic compounds; Pyrroles; Reaction products
Přiložené soubory
Popis Bilirubin is the principal product of heme catabolism. High concentrations of the pigment are neurotoxic, yet slightly elevated levels are beneficial. Being a potent antioxidant, oxidative transformations of bilirubin occur in vivo and lead to various oxidized fragments. The mechanisms of their formation, intrinsic biological activities, and potential roles in human pathophysiology are poorly understood. Degradation methods have been used to obtain samples of bilirubin oxidation products for research. Here, we report a complementary, fully synthetic method of preparation. Our strategy leverages repeating substitution patterns in the parent tetracyclic pigment. Functionalized ready-to-couple gamma-lactone, gamma-lactam, and pyrrole monocyclic building blocks were designed and efficiently synthesized. Subsequent modular combinations, supported by metal-catalyzed borylation and cross-coupling chemistries, translated into the concise assembly of the structurally diverse bilirubin oxidation products (BOXes, propentdyopents, and biopyrrins). The discovery of a new photoisomer of biopyrrin A named lumipyrrin is reported. Synthetic bilirubin oxidation products made available in sufficient purity and quantity will support future in vitro and in vivo investigations.
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