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Synthesis of [3‐13C]‐, [4‐13C]‐ and [11‐13C]‐porphobilinogen
Authors:Prativa B. S. Dawadi  Els A. M. Schulten  Johan Lugtenburg
Affiliation:Leiden Institute of Chemistry, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands
Abstract:
[4‐13C]‐porphobilinogen 1a, [3‐13C]‐porphobilinogen 1b and [11‐13C]‐porphobilinogen 1c are prepared from [1‐13C]‐3‐(tetrahydropyran‐2′‐yloxy)‐propionaldehyde 2a, methyl [4‐13C]‐4‐nitrobutyrate 3b and [1‐13C]‐isocyanoacetonitrile 5c, respectively. The building blocks 2, 3 and 5 can be prepared efficiently in any isotopomeric form. Via base‐catalyzed condensation of these building blocks porphobilinogen can be enriched with 13C and 15N stable isotopes at any position and combination of positions. Copyright © 2009 John Wiley & Sons, Ltd.
Keywords:phorphobilinogen isotopomers  isotopic labeling  cyanopyrrole
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