title: 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).
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.
authors: Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University, Humboldtstrasse 8, D-07743 Jena, Germany.
authors: Maurice
authors: M
authors: Klopfleisch
authors: Raphael A
authors: RA
authors: Seidel
authors: Helmar
authors: H
authors: Görls
authors: Hannes
authors: H
authors: Richter
authors: Rainer
authors: R
authors: Beckert
authors: Wolfgang
authors: W
authors: Imhof
authors: Markus
authors: M
authors: Reiher
authors: Georg
authors: G
authors: Pohnert
authors: Matthias
authors: M
authors: Westerhausen
mesh_terms: D001663:Bilirubin / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C586359:(Z)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide; D011758:Pyrroles; D001663:Bilirubin