title: The design, synthesis and photochemical study of a biomimetic cyclodextrin model of photoactive yellow protein (PYP).
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.
authors.affiliation: Département de Chimie, UMR-CNRS 7203, Ecole Normale Supérieure, 24 rue Lhomond, 75005 Paris, Cedex 05, France.
authors.forename: Christina
authors.initials: C
authors.lastname: Loukou
authors.forename: Pascale
authors.initials: P
authors.lastname: Changenet-Barret
authors.forename: Marie-Noelle
authors.initials: MN
authors.lastname: Rager
authors.forename: Pascal
authors.initials: P
authors.lastname: Plaza
authors.forename: Monique M
authors.initials: MM
authors.lastname: Martin
authors.forename: Jean-Maurice
authors.initials: JM
authors.lastname: Mallet
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D010782:Photolysis; D020283:Photoreceptors, Microbial / Q000737:chemistry*
chemical_list: D001426:Bacterial Proteins; D003505:Cyclodextrins; D020283:Photoreceptors, Microbial; C050162:photoactive yellow protein, Bacteria