2009
DOI: 10.1007/s11084-009-9168-3
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Simple Formation of an Abiotic Porphyrinogen in Aqueous Solution

Abstract: Porphyrins have long been proposed as key ingredients in the emergence of life yet plausible routes for forming their essential pyrrole precursor have heretofore not been identified. Here we show that the anaerobic reaction of δ-aminolevulinic acid (ALA, 1-5 mM) with the β-ketoester methyl 4-methoxyacetoacetate (2-40 mM) in water (pH5-7) at 70-100°C for >6 h affords the porphyrinogen, which upon chemical oxidation gives the corresponding porphyrin in overall yield of up to 10%. The key intermediate is the α-me… Show more

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Cited by 42 publications
(67 citation statements)
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“…Of the four possible isomers, the type III isomer is the only unsymmetrical variant, and it could be that nature has selected this lack of symmetry as a molecular handle or reference point for further modification of the molecule (148). However, the type III isomer is also the most abundant isomer formed when PBG is left under acidic (nonenzymatic) conditions, suggesting that this variant would have been more prevalent within a prebiotic soup and therefore more available for biological selection (149).…”
Section: Dailey Et Almentioning
confidence: 99%
“…Of the four possible isomers, the type III isomer is the only unsymmetrical variant, and it could be that nature has selected this lack of symmetry as a molecular handle or reference point for further modification of the molecule (148). However, the type III isomer is also the most abundant isomer formed when PBG is left under acidic (nonenzymatic) conditions, suggesting that this variant would have been more prevalent within a prebiotic soup and therefore more available for biological selection (149).…”
Section: Dailey Et Almentioning
confidence: 99%
“…This might suggest the existence of an additional MK biosynthetic pathway. Of course one could also argue that non-enzymatic haem synthesis, which does work [238], is the ancestral state used by the common ancestor. However, a more problematic aspect of the cytochromes first model is that, in that view, both methanogens and acetogens are seen as very late and highly derived evolutionary lineages [212], whereas isotope evidence has it that methanogens are ancient [164] and comparative physiology would have it that the core biochemistry of both methanogens and acetogens is ancient [44,73,160].…”
Section: Haem and Menaquinonementioning
confidence: 99%
“…Many Urey-Miller-type experiments have readily produced oligopyrroles and porphyrins abiotically using various sources of energy, including electrical discharges (Hodgson and Ponnamperuma, 1968;Simionescu et al, 1978), UV irradiation (Szutka, 1964;Hodgson and Baker, 1967;Meierhenrich et al, 2005), and high temperatures of 70-100 • C, compatible with a prebiotic milieu (Lindsey et al, 2009). Porphyrin-like substances have even been found in meteorites (Hodgson and Baker, 1964) and Precambrian rocks (Kolesnikov and Egorov, 1977).…”
Section: World Of Pigment-carrying Protocells (Earlymentioning
confidence: 99%