کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5372449 | 1388881 | 2006 | 13 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: UV-induced generation of rare tautomers of allopurinol and 9-methylhypoxanthine - A matrix isolation FTIR study UV-induced generation of rare tautomers of allopurinol and 9-methylhypoxanthine - A matrix isolation FTIR study](/preview/png/5372449.png)
Monomers of allopurinol and 9-methylhypoxanthine were studied using the matrix isolation technique combined with Fourier transform infrared spectroscopy. The oxo tautomeric forms of both compounds were found to dominate in freshly deposited low-temperature argon matrices. For 9-methylhypoxanthine, a small amount of the hydroxy tautomer was also detected in an Ar matrix before any irradiation. Upon exposure of the matrices to the UV (λ > 230 nm or λ > 270 nm) light, a proton transfer photoreaction converting the oxo forms of both compounds into the corresponding hydroxy tautomers occurred. Generation of conjugated ketenes as minor photoproducts was also observed. For 4(3H)-pyrimidinone (a model compound for both allopurinol and 9-methylhypoxanthine), photoreversibility of the UV-induced oxo â hydroxy transformation was experimentally proven by direct observation of the back hydroxy â oxo photoreaction. The substrates (oxo tautomers) and products (hydroxy tautomers) of the observed phototransformations were identified by comparison of their IR spectra with the spectra theoretically predicted at the DFT(B3LYP)/6-31++G(d,p) level. The IR bands in the experimental spectra were assigned to the calculated normal modes.
Journal: Biophysical Chemistry - Volume 122, Issue 2, 20 July 2006, Pages 123-135