Biogeochemistry of molecular complexes of amino acids with chlorins and porphyrins

Physics

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Scientific paper

Porphyrins and chlorins in vivo are closely associated with proteins, either through chemical bonding or through weak physical bonding. Chemical bonds can be formed between synthetic porphyrins and specific amino acids, for example between mesoporphyrin IX and phenylalanine as shown in the present study, under conditions that are plausible in a geochemical context. Not only can peptide bonds be formed utilizing carboxylic acid substituents of por- phyrin molecules, but molecular complexes can be synthesized by adding the amino group of amino acids to vinyl substituents of porphyrins and chlorins. This is illustrated by reacting phenylalanine with protoporphyrin IX. The biogeochemical significance of such intermolecular complexes lies not only in the simple diagenesis of biogenic compounds, as indicated by the observation that porphyrins of ancient sedimentary rocks and petroleum may possibly retain primary and secondary associations with bound amino acids, but also in prebiotic aspects of chemical evolution, wherein demonstration of the coupling of such compounds is of importance in establishing basic structures for the onset of life processes.

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