title: Abiogenic Syntheses of Lipoamino Acids and Lipopeptides and their Prebiotic Significance.
abstract: Researchers have formed peptide bonds under a variety of presumed prebiotic conditions. Here it is proposed that these same conditions would have also formed amide bonds between fatty acids and amino acids, producing phosphate-free amphipathic lipoamino acids and lipopeptides. These compounds are known to form vesicles and are ubiquitous in living organisms. They could represent molecules that provided protection by membranes as well as possibilities for proto-life metabolism . It is here demonstrated that when a fatty acid is heated with various amino acids, optimally in the presence of suitable salts or minerals, lipoamino acids are formed. Magnesium and potassium carbonates as well as iron (II) sulfide are found to be particularly useful in these reactions. In this manner N-lauroylglycine, N-lauroylalanine, N-stearoylalanine and several other lipoamino acids have been synthesized. Similarly, when glycylglycine was heated with lauric acid in the presence of magnesium carbonate, the lipopeptide N-lauroylglycylglycine was formed. Such compounds are proposed to have been critical precursors to the development of life.
authors.affiliation: University of South Carolina Beaufort, 801 Carteret St, Beaufort, SC, 29902, USA, gdsproul@uscb.edu.
authors.forename: Gordon
authors.initials: G
authors.lastname: Sproul
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D019418:Evolution, Chemical; D005227:Fatty Acids / Q000737:chemistry*; D055666:Lipopeptides / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D005227:Fatty Acids; D055666:Lipopeptides