Achiral N9-benzylguanine derivatives with alkene moieties attached to the benzyl group
were synthesized with the intent of targeting a covalently linked unimolecular quadruplex using olefin
cross-metathesis. Three N9-(3,5-bis(alkenyloxy)benzyl)-guanine derivatives were synthesized and
shown to form stable G-quartet structures in the presence of a central cation. Upon the addition of K+,
the guanine derivative, N9-(3,5-Bis(pent-4-en-1-yloxy)benzyl)-guanine, self-assembled into a discrete
[G]12-dodecamer quadruplex structure.
Keywords: Guanine, benzylguanine, DNA, dodecamer, G-quartet, G-quadruplex.
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