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Communication | Special issue | Vol 15, No. 2, 1981, pp.919-923
Published online:
DOI: 10.3987/S-1981-02-0919
Condensation Products of the Porphyrin Precursor 5-Aminolevulinic Acid

Burchard Franck* and Helmut Stratmann

*Organisch-Chemisches Institut, Universität Münster, Orleansring 23,D-4400 Münster, Germany

Abstract

Condensation of the biogenetic porphyrin precursor 5-aminolevulinic acid (1) in alkaline solution yields besides some porphobilinogen (2) a dihydropyrazine (6) as the predominant product, which was isolated and characterized after dehydrogenation to the stable pyrazine (7a). This ends a longstanding uncertainty and reveals that the azomethine reaction, as can be expected for α-aminoketones, is strongly preferred by 5-aminolevulinic acid (1) under nonenzymatic conditions. A nor-porphobilinogen (9) was formed by condensation of a protected aminoacetoacetic ester with (1).

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