Browsing by Subject "TORC"

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Sequenceable Sequence-Defined Oligourethanes as a Medium for Information Storage
(2020-05-08) Boley, Alexander J.; Anslyn, Eric V.
Physical data storage is an increasingly active field of research. Potential storage media such as DNA or RNA can encode sufficient information to be viable, but they are not stable in the long term. A potential alternative to these heavily studied polymers presented itself in plastics, especially the linear polymers of oligourethanes. These plastics demonstrate both the information density and stability necessary for long-term storage of encoded data, so long as individual units can be decoded and read at a later time. Previous work determined appropriate sequencing conditions for stepwise degradation of the oligourethanes, allowing for the reverse engineering of the sequence-defined polymer. With this proof of concept of information storage, focus was shifted toward solid phase synthesis, labeling, and sequencing of polyurethanes with diverse monomers bearing variable functionalities, to assess stability in the degradation conditions. Interest in the inclusion of Tunable Orthogonal Reversible Covalent (TORC) bonds served as the impetus for the synthesis of a Lysine-based monomer capable of “click” reactions. This monomer was successfully synthesized, integrated into a sequence-defined oligourethane, and modified with a TORC functionality using click chemistry. Moving forward, the project will focus on the sequencing of sequence-defined oligourethanes containing this and other monomers bearing variable functionalities, as well as investigating the capability of TORC-functionalized oligourethanes to form higher-ordered structures akin to DNA.
TORC Bonding Pairs as an Alternative to Nucleobases in Self Replicating Polymers
(2020-11) van der Stok, Aevi; Anslyn, Eric V.
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.