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Synthesis of [3‐ 13 C]‐, [4‐ 13 C]‐ and [11‐ 13 C]‐porphobilinogen
Author(s) -
Dawadi Prativa B. S.,
Schulten Els A. M.,
Lugtenburg Johan
Publication year - 2009
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.1602
Subject(s) - porphobilinogen , chemistry , porphobilinogen synthase , stereochemistry , dehydratase , organic chemistry , enzyme
[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.