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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Sequence-Dependent Folding of Recognition-Encoded Melamine Oligomers
Anca-Luiza Cotîrlan1, Cecilia J Anderson1, Nia E J Eyre1
1Yusuf Hamied Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
Recognition-encoded melamine oligomers (REMO) fold like nucleic acids. Sequence dictates folding, with specific designs achieving high stability and cooperativity for hairpin and helical structures.
Area of Science:
- Supramolecular Chemistry
- Polymer Chemistry
- Organic Chemistry
Background:
- Melamine oligomers with specific side chains can mimic nucleic acid folding.
- Understanding sequence-dependent folding is crucial for designing functional supramolecular systems.
Purpose of the Study:
- To investigate the sequence-dependent folding properties of recognition-encoded melamine oligomers (REMO).
- To quantify intramolecular base-pairing and explore hairpin and helical structure formation in REMO.
Main Methods:
- Automated solid-phase synthesis of REMO with varying linker lengths and recognition units.
- UV-vis absorption denaturation experiments in perfluoro-tert-butanol/dichloromethane to assess base-pairing.
- Analysis of folding populations, effective molarities (EMf), and cooperativity (α) for different sequences.
Main Results:
- REMO exhibit sequence-dependent folding, similar to single-stranded nucleic acids.
- Oligomers with complementary end units showed 50-90% folded states, influenced by sequence.
- Hairpin structures (ADO4AD, ADO5AD) demonstrated high cooperativity (α > 10) and 96% folded state.
- Helical structures (DAO4AD) aligned with a hexagonal grid model, indicating backbone conformational preferences.
Conclusions:
- Sequence-structure relationships in REMO are key to achieving stable folding motifs.
- Alignment of recognition sites with backbone conformational preferences drives favorable folding.
- REMO offer a versatile platform for creating predictable folded structures with potential applications in molecular recognition and self-assembly.
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