Fluorescent amino acids as reporter systems in peptido-cyclodextrin inclusion compounds

Mohamed Eddaoudi, Helene Parrot-Lopez, Sophie Frizon De Lamotte, Damien Ficheux, Patrice Prognon, Anthony W. Coleman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The inclusion behaviour of mono-6-(N-acetyltyrosinyl)amino-6-deoxy-β- cyclodextrin and mono-6-(N-acetyltryptophanyl)amino-6-deoxy-β-cyclodextrin with regard to borneol, menthol and 5-methoxypsoralen have been investigated by fluorescence spectroscopy, circular dichroism and NMR spectroscopy. For mono-6-(N-acetyltryptophanyl)amino-6-deoxy-β-cyclodextrin, the weakly self-included indole residue is disincluded, and for 5-methoxypsoralen, fluorescence resonant energy transfer is observed. In contrast, for mono-6-(N-acetyltyrosinyl)amino-6-deoxy-β-cyclodextrin the self-inclusion is sufficiently strong that no disinclusion occurs. A binary complex is postulated to arise from hydrogen bonding between borneol and mono-6-(N-acetyltyrosinyl)amino-6-deoxy-β-cyclodextrin.

Original languageEnglish (US)
Pages (from-to)1711-1715
Number of pages5
JournalJournal of the Chemical Society. Perkin Transactions 2
Volume8
StatePublished - Jan 1 1996

ASJC Scopus subject areas

  • Chemistry(all)

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