Novel photosystem involving protonation and deprotonation processes modelled on a PYP photocycle.
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.
Matsuhira
Takashi
T
Department of Macromolecular Science, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan.
Tsuchihashi
Kazuki
K
Yamamoto
Hitoshi
H
Okamura
Taka-aki
TA
Ueyama
Norikazu
N
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
D000577:Amides; D001426:Bacterial Proteins; D003373:Coumaric Acids; D020283:Photoreceptors, Microbial; D011522:Protons; C050162:photoactive yellow protein, Bacteria; D019800:Phenol