@article {Vrantza2006,
	title = {{Modification of Guanine with PhotolabileN-Hydroxypyridine-2(1H)-thione: Monomer Synthesis, Oligonucleotide Elaboration, and Photochemical Studies}},
	journal = {Helv. Chim. Acta},
	volume = {89},
	number = {10},
	year = {2006},
	month = {oct},
	pages = {2371{\textendash}2386},
	abstract = {The photochemistry of N-hydroxypyridine-2(1H)-thione (NHPT), inserted as a photolabile modifier at the 6-position of 2'-deoxyguanosine or guanosine, has been evaluated. In particular, 6-[(1-oxidopyridin-2-yl)sulfanyl]- (1a) and 6-[(pyridin-2-yl)sulfanyl]-2',6-dideoxyguanosine (2a), novel photolabile derivatives of the natural nucleosides, were synthesized and characterized. The observed photolysis products of 1a in organic solvents could only be rationalized by assuming a rapid equilibrium with the corresponding 6-[(2-thioxopyridin-1(2H)-yl)oxy] analogue 3a (Scheme 5). Transient spectroscopy of 1a indicated a strong triplet-excited state suitable for triplet {\textrightarrow} triplet energy transfer or singlet-oxygen generation. The NHPT function was stable enough for (slightly modified) automated solid-phase oligonucleotide synthesis. The utility of the above compounds is discussed, as well as their potential use in photosensitization of reactive oxygen species in DNA. {\textcopyright} 2006 Verlag Helvetica Chimica Acta AG.},
	issn = {0018019X},
	doi = {10.1002/hlca.200690220},
	url = {http://doi.wiley.com/10.1002/hlca.200690220},
	author = {Vrantza, Despoina and Kaloudis, Panagiotis and Leondiadis, Leondios and Gimisis, Thanasis and Georgios C. Vougioukalakis and Orfanopoulos, Michael and Gasparutto, Didier and Cadet, Jean and Encinas, Susana and Paris, Cecilia and Miranda, Miguel A.}
}
