99986-59-1Relevant academic research and scientific papers
Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants
Lindsey, Jonathan S.,Chandrashaker, Vanampally,Taniguchi, Masahiko,Ptaszek, Marcin
, p. 65 - 75 (2011)
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. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011.
Reaction of some diketones with 5-aminolevulinic acid in acid solution
Butler,George
, p. 7017 - 7026 (2007/10/02)
Some 2,4-diketones react with 5-aminolevulinic acid in acid solution to form pyrroles. There are two modes of cyclisation, one leading to the Knorr and the other to the Fischer-Fink product. By a consideration of the products obtained from pentane-, hexane-, 3-methylpentane-, 3-isopropylpentane-, 3,3-dimethylpentane-, 1,1,1-trifluoropentane- 1,1,1,5,5,5-hexafluoro- pentane-2,4-dione and ethyl acetoacetate some generalisations concerning the formation of Knorr and Fischer-Fink products have been made. The reactions of 5-methyl-5-aminolevulinic acid with pentane- and 3-methylpentane-2,4-dione have also been examined. The relevance of these studies to the cyclic dimerisation of 5-aminolevulinic acid is discussed briefly.
