Molecules in dynamic combinatorial libraries react with one another reversibly to form a network of library members. Such dynamic combinatorial chemistries generate a mixture of compounds that interconvert into one another. Processes like self-assembly, folding, or hybridization can displace the equilibria, leading to emergent phenomena like replication. For example, library members who assemble are thermodynamically favored and can thus be selected. Various dynamic covalent bonds have been explored to create dynamic combinatorial libraries, including metathesis, hydrazone formation, disulfide exchange, peptide bond formation, or transamination . Such dynamic combinatorial libraries serve as a great model for the cellular reaction networks, which are also dynamic combinatorial libraries. For example, building blocks like nucleotides or amino acids form a vast library of oligonucleotides and proteins. Complex replication and translation machinery based on enzymes tightly regulate the product distribution in such networks in energy-consuming processes. When such reaction networks exist out of equilibrium, the abundance of library members is no longer solely controlled by thermodynamics but also by kinetics. As a model for biology's complex, out-of-equilibrium reaction networks, dynamic combinatorial libraries out of equilibrium have been designed. For example, in dissipative dynamic libraries, catalytic reaction cycles that convert reagents with high chemical potential (fuels) into products with low chemical potential (wastes) generate dynamic libraries that can only be at the expense of chemical potential. Specifically, fuel conversion into waste is required to form a dynamic covalent bond between library members of the combinatorial library. A backward reaction pathway breaks the bonds between the library members. The combination of fuel-driven bond formation and spontaneous bond cleavage means these dynamic covalent bonds are present, and library members can only exist when fuel is supplied. After the conversion of the fuel, the library will collapse towards equilibrium. For example, Otto described recently self-assembling selfreplicators based on disulfide exchange that require an oxidizing agent as fuel to form but are reacted back by reducing agents of the environment. The ability of a product to assemble catalyzed the formation of its building blocks, thereby shifting the concentrations away from the equilibrium conditions. Our group introduced transient anhydride linkages between isophthalic acid building blocks. In this system, the self-assembly and hybridization of oligomers also influenced the reaction kinetics by increasing the activation and decreasing the hydrolysis rates of certain library members. The scope of chemically fueled dynamic combinatorial libraries remains limited. Peptide-based building blocks can help to broaden the scope of such systems by the large variety of structures and straightforward preparation. Thus, in this work, we combine the power of chemically fueled dynamic combinatorial libraries with the vast library space of amino acids. We demonstrate how molecular design affects the outcome of the library and resulting self-assembled structures.