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Colin McGee ACF Abstract FY10

"Synthesis of novel cyclic heterocyclic compounds to interact with higher-order DNA"

Conference Name: Joint SERM/SWRM Regional Meeting

Nate Strong, Mike Agius*, Matt Schaenherr*, Colin McGee*, Tom Arusoo*, Mary Karpen and Toni Rice
Chemistry Department, Grand Valley State University, Allendale, MI 49401.

Higher-order DNA conformations can form within regions of DNA that are rich in guanines. Telomeric DNA is located at the end of human chromosomes, is guanine-rich and can fold into tetraplex DNA. Compounds that should interact and stabilize telomeric DNA are being developed. Increased binding affinity and selectively over duplex DNA is a long-term goal of this work. The convergent synthesis of novel, cyclic, heterocyclic compounds will be described. The intermediate monomeric units were synthesized using a building block approach involving acid chloride-amine coupling reactions. The final cyclization reaction was achieved via the use of peptide coupling reagents in combination with the cation template effect. Quantum mechanical calculations were used to help select the appropriate template ions for use in the synthesis. As tetraplex interactive ligands are typically planar, these calculations were also used to compare the shape of the new compounds to two previously published compounds. The results of this study will be described in this presentation.