Abstract
AbstractSeveral porphyrinyl‐nucleosides were prepared in the reaction of the OH group of one, two or four meso‐p‐hydroxyphenyl substituents of porphyrin with 5′‐O‐tosylates of 2′,3′‐O‐isopropylidene‐adenosine or ‐uridine, or 5′‐O‐tosylthymidine; the remaining porphyrin meso‐substituents were p‐tolyl, p‐hydroxyphenyl or 4‐pyridyl. The following porphyrinyl‐nucleosides were obtained with 8–17% yield: meso‐di(p‐tolyl)di(p‐phenylene‐5′‐O‐2′,3′‐O‐isopropylidene‐adenosine) (or ‐uridine)porphyrins 1,2, the respective meso‐tetranucleosideporphyrins 3,4‐meso‐mono(p‐phenylene‐5′‐O‐thymidine)porphyrins 5–7, meso‐di(p‐tolyl)di(p‐phenylene‐5′‐O‐thymidine)porphyrins 8,9 and the meso‐di(p‐hydroxyphenyl)di(p‐phenylene‐5′‐O‐thymidine)porphyrins 10. Other compounds prepared belonged to the series: meso(4‐pyridyl)4−n(p‐phenylene‐5′‐O‐2′,3′‐O‐isopropylideneuridine)nporphyrin, n = 1, 2 or 4, 11–13. N‐Methylation gave the water soluble iodide salts: (N‐methyl‐4‐pyridinium)44−n(p‐phenylene‐5′‐O‐2′,3′‐isopropylideneuridine)nporphyrins, n = 1, 2 or 4, 14–16. The ms fab showed in most cases stepwise detachment of the CH2(5′)‐nucleoside fragments.The porphyrins meso disubstituted by thymidine represent a convenient substrate for the build‐up of both nucleoside units into the oligo/polynucleotide chains.
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