G-quartet Formation from N9-Benzylguanine Derivatives

Title:G-quartet Formation from N9-Benzylguanine Derivatives

Volume: 15 Issue: 11

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*

Affiliation:

• Department of Chemistry and Biochemistry, Loyola Marymount University, Los Angeles, CA, 90045,United States

Keywords: Guanine, benzylguanine, DNA, dodecamer, G-quartet, G-quadruplex.

Abstract: 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.

Cite this article as:

Thurlow A. Lauren , Clay J. Khalyd , Wene P. Taylor , Groom L. Meg , Keyes S. Erin , Lang D. Alexis and McCallum E.B. Jeremy *, G-quartet Formation from N9-Benzylguanine Derivatives, Letters in Organic Chemistry 2018; 15 (11) . https://dx.doi.org/10.2174/1570178615666180329161419