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

doi:10.1039/p29960001711

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 journal › Article › peer-review

24 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 language	English (US)
Pages (from-to)	1711-1715
Number of pages	5
Journal	Journal of the Chemical Society. Perkin Transactions 2
Volume	8
DOIs	https://doi.org/10.1039/p29960001711
State	Published - Aug 1996
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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@article{2c09046a1e8b43d48aaacc271c04a52b,

title = "Fluorescent amino acids as reporter systems in peptido-cyclodextrin inclusion compounds",

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.",

author = "Mohamed Eddaoudi and Helene Parrot-Lopez and {De Lamotte}, {Sophie Frizon} and Damien Ficheux and Patrice Prognon and Coleman, {Anthony W.}",

year = "1996",

month = aug,

doi = "10.1039/p29960001711",

language = "English (US)",

volume = "8",

pages = "1711--1715",

journal = "Journal of the Chemical Society. Perkin Transactions 2",

issn = "0300-9580",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - Fluorescent amino acids as reporter systems in peptido-cyclodextrin inclusion compounds

AU - Eddaoudi, Mohamed

AU - Parrot-Lopez, Helene

AU - De Lamotte, Sophie Frizon

AU - Ficheux, Damien

AU - Prognon, Patrice

AU - Coleman, Anthony W.

PY - 1996/8

Y1 - 1996/8

N2 - 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.

AB - 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.

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U2 - 10.1039/p29960001711

DO - 10.1039/p29960001711

M3 - Article

AN - SCOPUS:54249127071

SN - 0300-9580

VL - 8

SP - 1711

EP - 1715

JO - Journal of the Chemical Society. Perkin Transactions 2

JF - Journal of the Chemical Society. Perkin Transactions 2

ER -

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

Abstract

ASJC Scopus subject areas

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