End of the summer

I can’t believe that the summer research has come to an end! So far, I have successfully synthesized and identified our products of interest in the lab, and they were sent for biological testing. Byproducts were also identified, which provides further insights for the reaction mechanisms. The new reaction has worked out well, with some preliminary yet promising results. The next step would be further purification of the products to confirm our hypothesis. If everything works out well in the end, it will be a first-time synthetic route for a natural molecule that has its biological activities confirmed in literature.

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Natural Products Synthesis (3)

Research in science has not always been easy. For four weeks, we have been trying to identify our hypothesized product in our new reaction pathway, but all the effort seems to be futile. It turns out that our one step reaction has yield more than 10 byproducts, which is unexpected. That also causes great challenge in separating and finding the molecules we want among endless byproducts. Given the scale of the reaction, numerous products are yielded in the order of milligrams, and the identification of molecules is a real challenge.

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Natural Products Synthesis (2)

The most important part of our research in week 3-4 lies in the successful synthesis of prenylated methyl-p-benzoquinone products with pure NMR spectra obtained for publication. This involved prolonged reaction monitoring, doing overnight NMR experiment, and a little bit of luck. Luckily our experimental data confirmed our research hypothesis and the synthesized products are on their way to a lab in Germany for further biological testing!

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Natural Product Synthesis (1)

The first two weeks in the lab began with setting up the lab and making necessary stock solutions and solvent systems for organic synthesis. The goal for this summer is to continue to investigate the reaction mechanisms of p-methylbenzoquinone and prenyl bromide, a novel one-step synthesis to attach the prenyl side chain onto the quinone molecule. Through extensive literature research, we have confirmed that our concise synthetic methods that have developed over the last two years are not reported in any peer-reviewed journals. In addition, we have yielded two regioisomers on para and meta positions, with meta isomer being the first-time synthetic product. Although the reaction mechanisms are still elusive at this time (and will be unexplainable in a long future), we have confirmed the identity of the molecules through rigorous analytical methods.

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Concise Synthesis and Biological Testing of Natural Products with Potential Anticancer Activity

Natural products are organic compounds that are generated by living organisms as secondary metabolites and may function as defense chemicals. A wide range of natural products have been identified to have significant inhibitory activity vs. certain enzymes. Our products of interest are derivatives of quinones. Modified quinones are a group of molecules found naturally in plants and often exhibit a wide array of biological activities including inhibitory response linked to cancer cell death. However, as they are only generated by organisms in very small amount, the extraction of the molecules from a natural source for biological assays is infeasible. Thus, the research question I hope to answer is how to design and execute novel and innovative synthetic methodologies to produce quinone derivatives in sufficient quantities to test their anticancer activities.

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