Total synthesis and detection of the bilirubin oxidation product (Z)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide (Z-BOX A)

Org Lett. 2013 Sep 6;15(17):4608-11. doi: 10.1021/ol402221b. Epub 2013 Aug 27.

Abstract

The selective total synthesis of the pure Z-isomer of BOX A (8a), a product of oxidative heme degradation with significant physiological impact, was achieved in four to six steps starting from 3-bromo-4-methylfuran-2,5-dione (1). Z-BOX A forms a strong hydrogen bridge framework in the crystalline state. LC-MS techniques allow identification and characterization of isomeric forms of BOX A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bilirubin* / analysis
  • Bilirubin* / chemistry
  • Bilirubin* / metabolism
  • Chromatography, High Pressure Liquid
  • Molecular Structure
  • Oxidation-Reduction
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Stereoisomerism

Substances

  • (Z)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide
  • Pyrroles
  • Bilirubin