Jump to main content
Jump to site search

Issue 1, 2011
Previous Article Next Article

Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants

Author affiliations

Abstract

Tetrapyrrole macrocycles (e.g., porphyrins) have long been proposed as key ingredients in the emergence of life, yet plausible routes for forming their essential pyrrole precursor have previously not been identified. Here, the anaerobic reaction of δ-aminolevulinic acid (ALA, 5–240 mM) with 5-methoxy-3-(methoxyacetyl)levulinic acid (1-AcOH, 5–240 mM) in water (pH 5–7) at 25–85 °C for a few hours to a few days affords uroporphyrinogen, which upon chemical oxidation gives uroporphyrin in overall yield of up to 10%. The key intermediate is the α-methoxymethyl-substituted analogue of the pyrrole porphobilinogen (PBG). Reaction of ALA and the decarboxy analogue of 1-AcOH (1-Me) gave coproporphyrinogen (without its biosynthetic precursor uroporphyrinogen as an intermediate); oxidation gave the corresponding coproporphyrin in yields comparable to those for uroporphyrin. In each case a mixture of porphyrin isomers was obtained, consistent with reversible oligopyrromethane formation. The route investigated here differs from the universal extant biosynthetic pathway to tetrapyrrole macrocycles, where uroporphyrinogen (isomer III) – nature's last common precursor to corrins, heme, and chlorophylls – is derived from eight molecules of ALA (via four molecules of PBG). The demonstration of the spontaneous self-organization of eight acyclic molecules to form the porphyrinogen under simple conditions may open the door to the development of a chemical model for the prebiogenesis of tetrapyrrole macrocycles.

Graphical abstract: Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 18 Sep 2010, accepted on 14 Oct 2010 and first published on 06 Dec 2010


Article type: Paper
DOI: 10.1039/C0NJ00716A
Citation: New J. Chem., 2011,35, 65-75
  •   Request permissions

    Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants

    J. S. Lindsey, V. Chandrashaker, M. Taniguchi and M. Ptaszek, New J. Chem., 2011, 35, 65
    DOI: 10.1039/C0NJ00716A

Search articles by author