13C-labeled bilirubin: synthesis of 31(32),171(172)-di-[13C]-mesobilirubin-XIIIα

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Abstract

The title compound, labeled with 13C in the ethyl groups was synthesized from K13CN and low-molecular-weight components. The synthetic relay compound was 31(32)[13C]-xanthobilirubinic acid methyl ester in a synthetic route that leads to a label in the ethyl β-substituent of a dipyrrinone model for bilirubin. This labeled dipyrrinone was oxidatively coupled to the dimethyl ester of mesobiliverdin-XIIIα, thereby providing a route to a 13C-labeled mesobiliverdin and mesobilirubin, with one carbon of each ethyl being 98% 13C-enriched.

Graphical Abstract

Keywords

Pyrrole Synthesis 13C-isotope 
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Notes

Acknowledgments

We thank the US National Institutes of Health (HD 17779) for generous support of this research. Dr Stefan E. Boiadjiev is on leave from the Institute of Organic Chemistry, Sofia, Bulgaria. We thank the US National Science Foundation (CHE-0521191) for matching funds to acquire a 400 MHz NMR spectrophotometer and upgrade our 500 MHz NMR.

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Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of NevadaRenoUSA

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