Detailed Information on Publication Record

@article{60401,
   author = {Mujawar, Taufiqueahmed Pirsaheb and Sevelda, Petr and Madea, Dominik and Klán, Petr and Švenda, Jakub},
   article_location = {Washington},
   article_number = {2},
   doi = {http://dx.doi.org/10.1021/jacs.3c11778},
   keywords = {Alkyls; Cross coupling reaction; Organic compounds; Pyrroles; Reaction products},
   language = {eng},
   issn = {0002-7863},
   journal = {Journal of the American Chemical Society},
   title = {A Platform for the Synthesis of Oxidation Products of Bilirubin},
   url = {https://pubs.acs.org/doi/10.1021/jacs.3c11778},
   volume = {146},
   year = {2024}
}

TY  - JOUR
ID  - 60401
AU  - Mujawar, Taufiqueahmed Pirsaheb - Sevelda, Petr - Madea, Dominik - Klán, Petr - Švenda, Jakub
PY  - 2024
TI  - A Platform for the Synthesis of Oxidation Products of Bilirubin
JF  - Journal of the American Chemical Society
VL  - 146
IS  - 2
SP  - 1603-1611
EP  - 1603-1611
PB  - American Chemical Society
SN  - 0002-7863
KW  - Alkyls
KW  - Cross coupling reaction
KW  - Organic compounds
KW  - Pyrroles
KW  - Reaction products
UR  - https://pubs.acs.org/doi/10.1021/jacs.3c11778
N2  - 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.
ER  - 

MUJAWAR, Taufiqueahmed Pirsaheb, Petr SEVELDA, Dominik MADEA, Petr KLÁN and Jakub ŠVENDA. A Platform for the Synthesis of Oxidation Products of Bilirubin. \textit{Journal of the American Chemical Society}. Washington: American Chemical Society, 2024, vol.~146, No~2, p.~1603-1611. ISSN~0002-7863. Available from: https://dx.doi.org/10.1021/jacs.3c11778.