Synthesis and triplex forming properties of an acyclic N7-glycosylated guanine nucleoside |
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Authors: | A St Clair G Xiang LW McLaughlin |
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Affiliation: | Department of Chemistry, Merkert Chemistry Center, Chestnut Hill, MA 02167, USA. |
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Abstract: | A chiral acyclic nucleoside, one in which the ribose carbohydrate has been replaced with a glycerol-based linker, is prepared by glycosylating guanine at the N7-nitrogen. The stereochemically pure derivative is converted to a DMT-protected phosphoramidite for incorporation into DNA sequences. Sequence containing the acyclic N7-dG nucleoside are capable of forming DNA triplexes in which it is likely that the N1-H and N2-amino groups of the N7-dG are involved in recognition of the guanine base in G-C base pairs. |
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