Thiol ester-linked p-coumaric acid as a new photoactive prosthetic group in a protein with rhodopsin-like photochemistry.
A number of Eubacteria contain a photoactive yellow protein which has a photosensory function in negative phototaxis. It has been proposed that the cofactor responsible for the intense yellow color of this protein is retinal [McRee, D. E., et al. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 6533-6537]. This would make it the first eubacterial rhodopsin. Here we report the chemical structure of this chromophoric group to be p-coumaric acid, which is covalently bound to a unique cysteine in the apoprotein via a thiol ester bond, and thus not retinal. This makes PYP the first example of a protein containing p-coumaric acid, a metabolite previously found only in plants, as a prosthetic group and establishes the photoactive yellow proteins as a new type of photochemically active receptor molecule.
Hoff
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WD
Department of Microbiology, E. C. Slater Institute, University of Amsterdam, The Netherlands.
Düx
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P
Hård
K
K
Devreese
B
B
Nugteren-Roodzant
I M
IM
Crielaard
W
W
Boelens
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R
Kaptein
R
R
van Beeumen
J
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Hellingwerf
K J
KJ
D002841:Chromatiaceae / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003373:Coumaric Acids / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry; D004229:Dithiothreitol / Q000494:pharmacology; D004952:Esters / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D010777:Photochemistry; D011422:Propionates; D012243:Rhodopsin / Q000737:chemistry*; D012972:Sodium Hydroxide / Q000494:pharmacology; D013438:Sulfhydryl Compounds / Q000737:chemistry
D003373:Coumaric Acids; D004220:Disulfides; D004952:Esters; D011422:Propionates; D013438:Sulfhydryl Compounds; D012972:Sodium Hydroxide; D012243:Rhodopsin; C495469:p-coumaric acid; D003545:Cysteine; D004229:Dithiothreitol