title: Novel photosystem involving protonation and deprotonation processes modelled on a PYP photocycle.
abstract: The synthesis of novel ortho-coumaric acid derivatives, with an amide group linked with an olefin moiety, which introduced photoinduced switching of the intramolecular hydrogen bonds is presented. An intramolecular OH...O=C hydrogen bond formed in a Z-phenol compound was switched to an intramolecular NH...O hydrogen bond in Z phenolate state via deprotonation. The pK(a) value of the Z-phenol derivative was lower than that of E-phenol, and a novel photocycle system involving protonation and deprotonation processes was achieved.
authors.affiliation: Department of Macromolecular Science, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Matsuhira
authors.forename: Kazuki
authors.initials: K
authors.lastname: Tsuchihashi
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Yamamoto
authors.forename: Taka-aki
authors.initials: TA
authors.lastname: Okamura
authors.forename: Norikazu
authors.initials: N
authors.lastname: Ueyama
mesh_terms: D000577:Amides / Q000737:chemistry; D001426:Bacterial Proteins / Q000737:chemistry* / Q000528:radiation effects*; D003373:Coumaric Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008954:Models, Biological; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D019800:Phenol / Q000737:chemistry; D010777:Photochemistry / Q000379:methods*; D020283:Photoreceptors, Microbial / Q000737:chemistry* / Q000528:radiation effects*; D011522:Protons; D016339:Spectrometry, Mass, Fast Atom Bombardment; D017550:Spectroscopy, Fourier Transform Infrared; D014466:Ultraviolet Rays
chemical_list: D000577:Amides; D001426:Bacterial Proteins; D003373:Coumaric Acids; D020283:Photoreceptors, Microbial; D011522:Protons; C050162:photoactive yellow protein, Bacteria; D019800:Phenol