PMID: 9188273Jun 1, 1997Paper

Isolation and partial characterization of a novel psoralen-tyrosine photoconjugate from a photoreaction of psoralen with a natural protein

Photochemistry and Photobiology
S S Sastry

Abstract

The photoreaction of psoralens with DNA is a well-characterized reaction. However, the photoreactions of psoralens with proteins is not very well understood. Our objective was to isolate an amino acid-psoralen photochemical adduct. We photoreacted 8-methoxypsoralen (8-MOP) with T7 RNA polymerase, a protein that carries out the fundamental biological process of transcription. Amino acid composition analysis of the photoreacted polymerase revealed that tyrosines quantitatively reacted with 8-MOP. From the acid hydrolysates of the photoconjugated T7 RNA polymerase, an 8-MOP-tyr adduct was partially purified by HPLC. The purified 8-MOP-tyr adduct and related parent compounds were analyzed by UV-visible absorption, fluorescence and mass spectroscopy. Excitation/absorption spectra suggested that the pyrone of the original 8-MOP was modified in the isolated photoadduct, and that the adduct probably contained a benzofuran. Chemical ionization mass spectrometry was consistent with the photoaddition of tyr to 8-MOP with a conservation of the overall mass (+/-1 atomic mass units). As far as we know, this work represents the first instance of isolation and partial characterization of an amino acid-psoralen photoadduct.

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Citations

Mar 31, 1999·Journal of Dermatological Science·D BetheaF P Gasparro
Oct 1, 2010·Photochemistry and Photobiology·John T ReillyTiffiany R Risher
Jul 26, 2002·Molecular and Cellular Biology·Joyce T Reardon, Aziz Sancar
Jan 29, 2014·Journal of the American Society for Mass Spectrometry·Michel PrudentNiels Lion
Sep 10, 2005·Photochemistry and Photobiology·L ChenLinda J Johnston
May 26, 2016·Chemistry : a European Journal·Nina SimonSabine Schneider
May 23, 1998·The Journal of Biological Chemistry·S Sastry, B M Ross
Aug 18, 2000·Photochemistry and Photobiology·P D WoodL J Johnston

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