Potential for minimal self-replicating systems in a dynamic combinatorial library of equilibrating imines

Article abstract of DOI:10.1016/j.tet.2017.06.045

The presence of a self-replicator in a dynamic combinatorial library (DCL) offers function above and beyond libraries under thermodynamic control, moving towards out-of-equilibrium systems which mimic biological networks. In this work, we examine a previously reported DCL based on reversible imine formation to give amphiphilic structures. The amphiphilic imines were readily produced in organic solvents, and were found to aggregate to micelles in water as judged by diffusion-ordered NMR spectroscopy, dynamic light scattering and interferometric scattering microscopy. Unfortunately, the autocatalytic formation of products was not observed in water, and preformed imines slowly hydrolysed to aldehyde and amine components at neutral pD.