Journal
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
Volume 66, Issue 1-2, Pages 195-208Publisher
SPRINGER
DOI: 10.1007/s10847-009-9687-6
Keywords
bis-1,3-Urea calix[4]arenes; Amino acids; Hydrogen bonding; Mass spectroscopy; Anion binding; Carboxylic acids
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Funding
- EPSRC [EP/E010814/1] Funding Source: UKRI
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We report the ability of urea's appended onto the upper-rim of conformationally locked 'cone' calix[4]arenes to show a preference for binding specific N-protected alpha-amino acids. Superior complexation (as judged by mass spectroscopy) between N-protected alpha-amino results and bis-1,3-N-benzylureas calix[4]arenes was observed when methylene bridges were present between the calix[4]arene 'host' and the urea motif. Interestingly we also demonstrate that subjecting mixtures of structurally diverse N-Fmoc-alpha-amino acids to a single bis-1,3-N-benzylurea derived calix[4]arene allows, in some cases, the calix[4]arene 'host' to selectively 'pick out' and complex a specific N-Fmoc amino acid from the mixture.
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