Synthesis and Triplex Forming Properties of an Acyclic N7-Glycosylated Guanine Nucleoside |
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| Authors: | Aimée St Clair Guobing Xiang Larry W McLaughlin |
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| Institution: | Department of Chemistry , Merkert Chemistry Center , 2609 Beacon St., Chestnut Hill, MA, 02167 |
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| Abstract: | 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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