Abstract
A novel mechanism enabling selective peptide elongation by coupling α-amino acids over other potentially competing prebiotic amines under acidic aqueous condition is suggested. It proceeds via the generation of a carboxylic acid anhydride intermediate with subsequent intramolecular formation of the amide bond.
Highlights
A novel mechanism enabling selective peptide elongation by coupling a-amino acids over other potentially competing prebiotic amines under acidic aqueous condition is suggested
We have previously shown that the chemical energy inherent in methyl isonitrile 1 – a potentially prebiotic activating reagent13 – can be harnessed to activate and join phosphate and carboxylate building blocks simultaneously under acidic aqueous conditions.[14]
We found that amide bond formation shows very limited selectivity for all amines examined at pH 5, regardless of the fact that the pKa values of their conjugate acids differ by up to 5.4 units
Summary
A novel mechanism enabling selective peptide elongation by coupling a-amino acids over other potentially competing prebiotic amines under acidic aqueous condition is suggested.
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