@article {Manetto2007a,
	title = {{Independent Generation of C5{\textquoteleft}-Nucleosidyl Radicals in Thymidine and 2{\textquoteleft}-Deoxyguanosine}},
	journal = {J. Org. Chem.},
	volume = {72},
	number = {10},
	year = {2007},
	month = {may},
	pages = {3659{\textendash}3666},
	abstract = {(Chemical Equation Presented) The synthesis of the C5' tert-butyl ketone of thymidine 1a and 2'-deoxyguanosine 2 is achieved by reaction of 5'-C-cyano derivatives with tert-butyl lithium followed by acid hydrolysis. The 5'R configuration is assigned by X-ray crystal structure determination of an opportunely protected derivative of 1a. The (5'S)-isomers of both nucleosides are not stable, and a complete decomposition occurs in the reaction medium. The photochemistry of 1a and 2 effectively produced the thymidin-5'-yl radical and the 2'-deoxyguanosin-5'-yl radical, respectively. In the thymidine system, the C5' radical is fully quenched in the presence of a physiological concentration of thiols. In the 2'-deoxyguanosine system, the C5' radical undergoes intramolecular attack onto the C8-N7 double bond of guanine leading ultimately to the 5',8-cyclo-2'-deoxyguanosine derivative. The cyclization of the 2'-deoxyguanosin-5'-yl radical occurs with a rate constant of ca. 1 {\texttimes} 106 s-1 and is highly stereoselective affording only the (5'S)-diastereomer. {\textcopyright} 2007 American Chemical Society.},
	issn = {0022-3263},
	doi = {10.1021/jo062518c},
	url = {http://pubs.acs.org/doi/abs/10.1021/jo062518c},
	author = {Manetto, Antonio and Georganakis, Dimitris and Leondiadis, Leondios and Gimisis, Thanasis and Mayer, Peter and Carell, Thomas and Chatgilialoglu, Chryssostomos}
}
