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The synthesis of [10‐ 13 C]bilirubin IXα
Author(s) -
Sturrock E. D.,
Bull J. R.,
Kirsch R. E.
Publication year - 1994
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580340309
Subject(s) - chemistry , biliverdin , formylation , dehydrohalogenation , bilirubin , yield (engineering) , dimethylformamide , derivative (finance) , biliverdin reductase , carboxylation , labelling , organic chemistry , heme , biochemistry , catalysis , heme oxygenase , medicine , materials science , solvent , gastroenterology , economics , financial economics , metallurgy , enzyme
The total synthesis of [10‐ 13 C]bilirubin IXα, the principal waste product of haem degradation, is described. Site specific labelling was accomplished by the Vilsmeier formylation of one of the dipyrrolic fragments using [1‐ 13 C]dimethylformamide. The penultimate dehydrohalogenation reaction was complicated by a competing elimination reaction which yielded a bridged biliverdin derivative. [10‐ 13 C]bilirubin IXα was prepared in an overall yield of 6% (from the step where 13 C was introduced) with quantitative isotopic incorporation.