A rotaxane mimic of the photoactive yellow protein chromophore environment: effects of hydrogen bonding and mechanical interlocking on a coumaric amide derivative.
Hydrogen bonding in a [2]rotaxane is shown to stabilise the phenolate anion of a coumaric amide chromophore by almost 3 pKa units; however, the effect on the UV spectral shift in the anion is small and, significantly given the photochemistry of PYP, despite the hydrogen bonding olefin photoisomerisation in the anionic rotaxane remains heavily suppressed.
Berná
José
J
Van 't Hqff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.
Brouwer
Albert M
AM
Fazio
Sandro M
SM
Haraszkiewicz
Natalia
N
Leigh
David A
DA
Lennon
Claire M
CM
D000577:Amides / Q000737:chemistry*; D001426:Bacterial Proteins / Q000737:chemistry*; D003198:Computer Simulation; D003373:Coumaric Acids / Q000737:chemistry*; D006860:Hydrogen Bonding; D007536:Isomerism; D008027:Light; D020283:Photoreceptors, Microbial / Q000737:chemistry*; D043862:Rotaxanes / Q000737:chemistry* / Q000528:radiation effects
D000577:Amides; D001426:Bacterial Proteins; D003373:Coumaric Acids; D020283:Photoreceptors, Microbial; D043862:Rotaxanes; C050162:photoactive yellow protein, Bacteria