Deoxyguanosine, chemical structure

Figure Chemical structure of the sulfur mustard adduct to the N7 position of 2 -deoxyguanosine. 

Moorthy PN, Hayon E (1975) Free-radical intermediates produced from the one-electron reduction of purine, adenine and guanine derivatives in water. J Am Chem Soc 97 3345-3350 Mori M, Teshima S-l, Yoshimoto H, Fujita S-l, Taniguchi R, Hatta H, Nishimoto S-l (2001) OH Radical reaction of 5-substituted uracils pulse radiolysis and product studies of a common redox-ambivalent radical produced by elimination of the 5-substituents. J Phys Chem B 105 2070-2078 Morin B, Cadet J (1995) Chemical aspects of the benzophenone-photosensitized formation of two lysine - 2 -deoxyguanosine cross-links. J Am Chem Soc 117 12408-12415 Morita H, Kwiatkowski JS,TempczykA(1981) Electronic structures of uracil and its anions. Bull Chem Soc Jpn 54 1797-1801... 

The ring structure of the sugar of the purine ribonucleosides was shown by chemical methods to be furanoid by Levene and Tipson. These studies have been adequately reviewed by Tipson. The fact that 2-deoxy-inosine and 2-deoxyguanosine do not affect the conductivity of boric acid solutions indicates the absence of a m-1,2-glycol system and, coupled with the anhydronucleoside formation mentioned below, provides evidence that the purine 2-deoxyribonucleosides are also in the furanoid form. 

Human exposures to chemicals found in certain foods or environmental pollutants are linked to a higher risk for cancer. It is known that the initial step in chemical carcinogenesis is the covalent attachment of the chemical to DNA to produce DNA adducts. The structure identification of these DNA adducts is very important in cancer research. CEC-ESI-MS with shealth liquid interface has been demonstrated as a good tool for the analysis of DNA adducts as well as nucleosides with styrene oxide by Vouros and co-authors [24, 25]. Two common DNA adducts, acetylaminofluorene deoxyguanosine (AAF-dG) and an isomer of anti-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide, were employed as model compounds. CEC separation was performed on a Cig silica gel-packed column and used a mixture of 60% acetonitrile and 5 mM ammonium acetate as the mobile phase. Figure 10 shows the extracted ion electrochromatograms and mass spectra of AAF-dG and benzo[g]chrysene-dG [25]. 

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