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Issue 7, 2011
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The design, synthesis and photochemical study of a biomimetic cyclodextrin model of Photoactive Yellow Protein (PYP)

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Abstract

The design, synthesis and study of the photophysical and photochemical properties of the first biomimetic cyclodextrin (CD) model of photoactive yellow protein (PYP) are described. This model bears a deprotonated trans-p-coumaric acid chromophore, covalently linked via a cysteine moiety to a permethylated 6-monoamino β-CD. NMR and UV/Visible spectroscopy studies showed the formation of strong self-inclusion complexes in water at basic pH. Steady-state photolysis demonstrated that, unlike the free chromophore in solution, excitation of the model molecule leads to the formation of a photoproduct identified as the cis isomer by NMR spectroscopy. These observations provide evidence that the restricted CD cavity offers a promising framework for the design of biomimetic models of the PYP hydrophobic pocket.

Graphical abstract: The design, synthesis and photochemical study of a biomimetic cyclodextrin model of Photoactive Yellow Protein (PYP)

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Publication details

The article was received on 30 Aug 2010, accepted on 13 Dec 2010 and first published on 07 Feb 2011


Article type: Paper
DOI: 10.1039/C0OB00646G
Citation: Org. Biomol. Chem., 2011,9, 2209-2218
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    The design, synthesis and photochemical study of a biomimetic cyclodextrin model of Photoactive Yellow Protein (PYP)

    C. Loukou, P. Changenet-Barret, M. Rager, P. Plaza, M. M. Martin and J. Mallet, Org. Biomol. Chem., 2011, 9, 2209
    DOI: 10.1039/C0OB00646G

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