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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

G-quartet Formation from N9-Benzylguanine Derivatives

Author(s): Lauren A. Thurlow, Khalyd J. Clay, Taylor P. Wene, Meg L. Groom, Erin S. Keyes, Alexis D. Lang and Jeremy E.B. McCallum*

Volume 15 , Issue 11 , 2018

Page: [909 - 914] Pages: 6

DOI: 10.2174/1570178615666180329161419

Price: $65


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.

Graphical Abstract

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