2011
DOI: 10.1039/c0cp02812f
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Five isomers of monomeric cytosine and their interconversions induced by tunable UV laser light

Abstract: Photoisomerization processes involving five isomers of cytosine were induced by narrowband tunable UV irradiation of matrix-isolated monomers of the compound. Irradiation of an argon matrix containing cytosine monomers with UV λ = 313 nm laser light resulted in syn↔anti photoisomerizations between the two imino-oxo forms, whereas the substantially more populated amino-hydroxy and amino-oxo forms stayed intact. Subsequent irradiation with shorter-wavelength UV λ = 311 nm laser light led to two concomitant photo… Show more

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Cited by 73 publications
(89 citation statements)
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“…The photo-tautomerization from the keto to imino form via the hydrogen-atom-transfer was observed at least in the matrix environments for cytosine 70 and also for 1-methylcytosine 71 , which have been later supported by the recent theoretical calculations. 72 It is also noted in passing that the ring-opening reactions from keto cytosine to the conjugated isocyanate products were reported 70 (which is known as the Norrish type I (α-bond cleavage) photoreaction 73 ). Better quantitative comparison with the experimental results must await the dynamical simulations including these possibilities.…”
Section: E Comparison With Experimental Findingssupporting
confidence: 54%
“…The photo-tautomerization from the keto to imino form via the hydrogen-atom-transfer was observed at least in the matrix environments for cytosine 70 and also for 1-methylcytosine 71 , which have been later supported by the recent theoretical calculations. 72 It is also noted in passing that the ring-opening reactions from keto cytosine to the conjugated isocyanate products were reported 70 (which is known as the Norrish type I (α-bond cleavage) photoreaction 73 ). Better quantitative comparison with the experimental results must await the dynamical simulations including these possibilities.…”
Section: E Comparison With Experimental Findingssupporting
confidence: 54%
“…This combined matrix isolation and laser irradiation technique has already been shown to be very useful to investigate tautomers and conformers of small biomolecules in the matrix, e.g. cytosine (Lapinski et al 2010(Lapinski et al ,2011 glycine (Bazsó et al 2012a, b), and alanine (Bazsó et al 2013;Nunes et al 2013). Selected cross-sections of the Ramachandran-type-cube of the cis-(S,R), the cis-(R,S), and the trans-(S,S) monomeric building units derived from 2-aminocyclobutane-1-carboxylic acid: S (spiral) and E (elongated) refer to additional possible conformations Initial geometries were obtained by a conformational search using the MMFF force field (Halgren 1996) implemented in the Macromodel 7.0 program (Mohamadi et al 1990).…”
Section: Discussionmentioning
confidence: 99%
“…The detailed results of harmonic and anharmonic frequency DFT calculations for the isolated nucleobases are reported in the supplementary material (Tables 1-5) where they are compared with the available experimental data. Assignments of vibrational modes were performed by visual inspection of the atomic displacements along normal modes and by comparison with the assignments reported in the literature 31,32,[34][35][36]39,[144][145][146][147] .…”
Section: Monomersmentioning
confidence: 99%