Appendix S1. Experimental details of the preparation and purification protocols for various photoproducts and descriptions of the partial characterizations of certain photoproducts of 5-methyl-2′-deoxycytidine.

Figure S1. The UV spectra of the “dh” products of 1,5-dimethylcytosine (Ib) and 1-methylthymine (IIb).

Figure S2. The UV spectra of three other photoproducts of 1,5-dimethylcytosine.

Figure S3. The UV spectra of the “dh” products of 5-methyl-2′-deoxycytidine (putatively Ic) and thymidine (IIc).

Figure S4. The proton NMR spectrum of the “dh” product of Thd (IIc).

Figure S5. The chromatogram resulting from HPLC of 5-MedCyd, irradiated at 254  nm in frozen aqueous solution.

Figure S6. The proton NMR spectrum of the “dh” product of 5-MedCyd.

Figure S7. The UV spectra of three 5-MedCyd photoproducts with either tentatively assigned or unassigned structures.

Figure S8. A possible mechanism leading to formation of the “spore” photoproducts of Thd.

Table S1. Correlations between compound designations (e.g. PH11), structural assignments (e.g.IIc) and compound type (e.g. Thd [α-4] conjugate).

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