## Abstract Porphobilinogen‐11‐^13^C was prepared by using benzyl 3‐(β‐methoxycarbonylethyl)‐4‐ (methoxycarbonylmethyl)‐2‐pyrrolecarboxylate as a starting material. A Vilsmeier‐Haak formylation with N,N′‐dimethylform‐^13^C‐amide gave the 2‐formylpyrrole, which was transformed into its oxime, and th
Synthesis of [3-13C]-, [4-13C]- and [11-13C]-porphobilinogen
✍ Scribed by Prativa B. S. Dawadi; Els A. M. Schulten; Johan Lugtenburg
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- French
- Weight
- 289 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
[4‐^13^C]‐porphobilinogen 1a, [3‐^13^C]‐porphobilinogen 1b and [11‐^13^C]‐porphobilinogen 1c are prepared from [1‐^13^C]‐3‐(tetrahydropyran‐2′‐yloxy)‐propionaldehyde 2a, methyl [4‐^13^C]‐4‐nitrobutyrate 3b and [1‐^13^C]‐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 ^13^C and ^15^N stable isotopes at any position and combination of positions. Copyright © 2009 John Wiley & Sons, Ltd.
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