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  Total syntheses of the bilirubin oxidation end product Z-BOX C and its isomeric form Z-BOX D

Schulze, D., Traber, J., Ritter, M., Görls, H., Pohnert, G., & Westerhausen, M. (2019). Total syntheses of the bilirubin oxidation end product Z-BOX C and its isomeric form Z-BOX D. Organic & Biomolecular Chemistry, (26): 6489. doi:10.1039/c9ob01117j.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0003-CE9C-6 Version Permalink: https://hdl.handle.net/21.11116/0000-0009-3C53-7
Genre: Journal Article

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 Creators:
Schulze, Daniel, Author
Traber, Juliane, Author
Ritter, Marcel, Author
Görls, Helmar, Author
Pohnert, Georg1, Author           
Westerhausen, Matthias, Author
Affiliations:
1External Organizations, ou_persistent22              

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 Abstract: Oxidative degradation products of bilirubin (BOXes) are biologically highly active and certain BOXes cause
long-lasting narrowing of cerebral blood vessels presumably with a significant role in subarachnoid
hemorrhage. Due to the fact that mode of action as well as fate of these BOXes is widely unknown, larger
amounts of these bilirubin degradation end products are required. The total synthesis of colorless
(Z)-3-(5-(2-amino-2-oxoethylidene)-4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoic acid (BOX C)
succeeds via a seven-step procedure with a total yield of 20%. Its isomeric form (Z)-3-(2-(2-amino-2-
oxoethylidene)-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoic acid (BOX D) can be prepared via
a five-step protocol with a yield of 30%. NMR and crystallographic studies reveal that charge delocalization
within the conjugated π-systems of BOXes C and D is negligible. Exposure of solutions of Z-BOX C
and Z-BOX D to bright sunlight leads to Z/E-isomerization and mixtures of the respective E/Z-BOXes C and D.

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 Dates: 2019-06-112019-06-12
 Publication Status: Published online
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 Identifiers: Other: EXT658
DOI: 10.1039/c9ob01117j
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Title: Organic & Biomolecular Chemistry
  Other : Organic and Biomolecular Chemistry
  Abbreviation : Org. Biomol. Chem.
Source Genre: Journal
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Publ. Info: Cambridge : Royal Society of Chemistry
Pages: - Volume / Issue: (26) Sequence Number: 6489 Start / End Page: - Identifier: ISSN: 1477-0520
CoNE: https://pure.mpg.de/cone/journals/resource/954925269322