TORC Bonding Pairs as an Alternative to Nucleobases in Self Replicating Polymers




van der Stok, Aevi

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The search for life on other planets is limited due to having only an incomplete knowledge of the origins of life on Earth as reference. While genetic information is stored and replicated by RNA and DNA using nucleobase chemistry here on Earth, this may not be the case on other planets with different environmental conditions. Tunable Orthogonal Reversible Covalent (TORC) bonds have promise in the creation of sequence-specific replicators because their orthogonality allows for the TORC bonding pairs to function similarly to nucleotide bases, defining and replicating the sequence, while their reversibility allows for duplexes to be separated for replication and their increased strength as covalent bonds would make these replicators more suitable to hot environments than the hydrogen bonding interactions observed in DNA replicators. This project represents the first step in the creation of sequence-specific TORC replicators by demonstrating the templating and synthesis of short peptide strands from a template strand using the hydrazone TORC bonding pair. In addition to this, macrocyclic products were also produced using these templates. This unexpected result holds promise for the creation of macrocyclic TORC replicators. The creation of macrocycles also has therapeutic applications, as macrocyclic peptides have useful properties but are generally difficult to synthesize, and the templates created in this project can quantitatively produce macrocyclic peptide products without any unwanted side products.



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