Abstract
A series of pyridyl guanidinium-carboxylates has been prepared and the dimeric self-assembly of these studied in H(2)O/DMSO mixtures, principally using dilution isothermal calorimetry. Compounds 5 and 6, incorporating an aromatic ring in the "tethering" region between the guanidinium and carboxylate groups, demonstrate the strongest dimerisation in neat DMSO. X-ray crystal structures of 5 and 6 reveal two different dimerisation architectures in the solid-state, but both involve carboxylate-guanidinium salt bridges as anticipated, and pi-pi interactions. Compounds 10-16 incorporating peptidic fragments between the guanidinium and carboxylate groups, showed reduced dimerisation strength with increased amino acid content, but also sustained dimerisation under increasingly aqueous conditions, up to 50% H(2)O/DMSO in the case of 14 and 15. The extent of our study in H(2)O/DMSO mixtures was determined by substrate solubility of 10-16, and not the limit of self-assembly.
Original language | English |
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Pages (from-to) | 12387-12397 |
Number of pages | 11 |
Journal | Chemistry : a European Journal |
Volume | 16 |
Issue number | 41 |
DOIs | |
Publication status | Published - 2010 |
Keywords
- calorimetry
- dimerization
- molecular recognition
- self-assembly
- supramolecular chemistry
- BETA-HAIRPIN PEPTIDE
- ENTHALPY-ENTROPY COMPENSATION
- SIDE-CHAIN INTERACTIONS
- AMINO-ACID BINDING
- THERMODYNAMIC ANALYSIS
- MOLECULAR RECOGNITION
- OXOANION BINDING
- MODEL SYSTEMS
- BIOMOLECULAR INTERACTIONS
- RECEPTOR LIBRARIES