K. Cheung, P. Shoolingin‐Jordan
Aug 20, 2001
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Journal
Tetrahedron Letters
Abstract
The octaethyl esters of uroporphyrins were formed directly from ethyl 3-(4-ethoxy-carbonylmethyl-1H-pyrrol-3-yl)propionate and formalin in a yield of ca. 30% with the isomers I, II, III and IV being formed in the ratio 1:1:4:2. Under anaerobic conditions, the colourless uroporphyrinogen esters were formed in a similar ratio. These observations parallel the non-enzymic formation of uroporphyrinogens from the naturally occurring tetrapyrrole precursor, porphobilinogen, highlighting the similarity in both tetramisation and isomerisation reactions.