This study shows that lipoamino acids can be obtained from their individual components, which are free amino acids and lipid precursors, and that octanoyl-L-histidine, C₈-His, outcompetes in its formation from a pool of natural amino acids and a family of lipids with a diverse chain length. The observed selectivity is purely based on kinetics, following an autocatalytic mechanism.

Abstract

Designing synthetic chemical systems capable of mimicking life-like behavior surely will help to understand the basic principles sustaining life, but also to create advanced materials potentially going beyond nature. Herein, we report the synthesis of a family of lipoamino acids from their individual components, which are free amino acids and lipid precursors, that allow us to study competition and selection in their formation. Octanoyl-L-histidine outcompetes from a pool of natural amino acids and a family of lipids, emerging as the fittest, where the observed selectivity is the result of a very efficient autocatalytic mechanism.