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G-quartet Formation from N9-Benzylguanine Derivatives

[ Vol. 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*   Pages 909 - 914 ( 6 )

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.

Keywords:

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

Affiliation:

Molecular Biology Institute, University of California Los Angeles, Los Angeles, CA, 90095, Department of Chemistry, The Scripps Research Institute, La Jolla, CA, 92037, Department of Science, Tyro Christian School, Tyro, KS, 67364, College of Medicine, The University of Arizona, Phoenix, AZ, 85004, Department of Medicine, University of California San Francisco, San Francisco, CA, 94117, USC School of Pharmacy, University of Southern California, Los Angeles, CA, 90089, Department of Chemistry and Biochemistry, Loyola Marymount University, Los Angeles, CA, 90045

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