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A synthesis of porphobilinogen‐11‐ 13 C
Author(s) -
Buldain Graciela,
Valasinas Aldonia
Publication year - 1982
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.2580190102
Subject(s) - chemistry , saponification , formylation , porphobilinogen , oxime , amide , hydrochloride , thienamycin , lactam , stereochemistry , organic chemistry , medicinal chemistry , catalysis , biochemistry , enzyme , antibiotics
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 the latter was hydrogenated to the hydrochioride of 5‐carboxyporphobilinogen dimethyl ester. The hydrochloride cyclized to 5‐carboxyporphobilinogen lactam at pH 9, and the latter was first decarboxylated and then saponified to give the title compound.