7600. Porphobilinogen

Nomenclature

CAS number: 487-90-1
5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propanoic acid; 2-aminomethylpyrrol-3-acetic acid 4-propionic acid.
C10H14N2O4; mol wt 226.23.
C 53.09%, H 6.24%, N 12.38%, O 28.29%.

Description and references

An intermediate in the biosynthesis of heme, q.v., found in the urine of patients with acute porphyria: Westall, Nature 170, 614 (1952). Isoln and structure: Cookson, Rimington, Biochem. J. 57, 476 (1954). Synthesis: Jackson, MacDonald, Can. J. Chem. 35, 715 (1957). Chemistry of conversion into porphyrins: Mathewson, Corwin, J. Am. Chem. Soc. 83, 135 (1961).

Chemical structure

Derivative

Monohydrate.

Properties

Minute pink crystals from dil ammonium acetate soln at pH 4. Dec 172-175°. pK′ = 3.70; 4.95; 10.1. Slightly sol in water. Converted to uroporphyrins by hot dil HCl or by blood hemolyzates.

Derivative

Hydrochloride monohydrate.

Properties

Fine triclinic needles from dil HCl, dec 165-170°. Soluble in water.