Mass spectroscopic investigation of bis-1,3-urea calix[4]arenes and their ability to complex N-protected α-amino acids

Sean P. Bew, Adam W. J. Barter, Sunil V. Sharma

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12 Citations (Scopus)


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 α-amino acids. Superior complexation (as judged by mass spectroscopy) between N-protected α-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-α-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. © Springer Science+Business Media B.V. 2009.
Original languageEnglish
Pages (from-to)195-208
Number of pages14
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Issue number1
Publication statusPublished - 1 Jan 2010

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