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. Author manuscript; available in PMC: 2015 Nov 14.
Published in final edited form as: Org Biomol Chem. 2014 Nov 14;12(42):8367–8378. doi: 10.1039/c4ob01063a

Fig. 7.

Fig. 7

2’-deoxyxanthosine (dX) ionizes at N3 with a pKa of about 5.7 (based on xanthosine) and is predominantly anionic at pH 7.4. Hydrolysis of neutral dX results in departure of the xanthine (X) monoanion, which should be a good leaving group, given that N9 is acidic for X relative to other purines, due perhaps to charge delocalization (N7, O6).