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2012 - 11th Annual NC State Summer Undergraduate Research Symposium
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Session Time :
8/1/12 1:30 PM - 8/1/12 2:45 PM
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Content Area : NC State Independent Researchers
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Lead Student Presenters : Andrew Mark McLean
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Abstract Title : Progress Toward the Synthesis of Analogues of Alotamide A
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Abstract :
A number of critical biological processes, including muscle contraction and neurotransmission, are modulated by calcium ion concentrations within cells. L-glutamate can result in excitotoxicity, where excessive stimulation of neuronal glutamate receptors and resultant Ca+2 influx overload will lead to neuron cell death. This is known to cause many contemporary neurodegenerative disorders such as Alzheimer’s, Huntington’s, etc. The focus of my project is the biologically active natural product alotamide A, which exhibits activation of Ca+2 influx in mouse cerebrocortical neurons. The goal of this inquiry is to develop a synthetic pathway to non-natural, simplified analogues of alotamide A using established synthetic procedures in order to better understand the effects of excitotoxicity. Retrosynthetically, we have chosen to break alotamide A into a tri-peptide based, thiazoline containing northern fragment and an aliphatic southern fragment. The northern fragment will be joined together using peptide coupling reactions while the southern fragment will be cyclized under ring-closing metathesis conditions. In the initial phase of the work three undefined stereocenters will be removed from the natural southern fragment in order to ease its synthetic preparation and begin structure-activity analysis.
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Mentor and/or Co-Author : Joshua Glenn Pierce
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