You Can’t Spell Funk without Fun!

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As Disney music fills the space of our lab, we (Andrew, Rowan, Tyler, and Kathryn) are hard at work in fume hoods. We want to do great chemistry but we also want to have great fun– because chemistry is fun! All four of us work in Dr. Funk’s lab (the funkiest lab around), however, there are three different projects going on. Kathryn and Andrew work on collecting kinetic data for the iron catalyst project. Rowan also works on the iron catalyst project but is specifically trying to synthesize lactones. Tyler is working on the design and synthesis of an organic linker that will ease the isolation of proteins modified with the GlcNAc functional group.

Meet the Squad

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My name is Kathryn Fodale, and I am a rising senior at Gettysburg College. I will graduate in 2016 with a BS in Chemistry. Working in the lab all summer is so fun! I love how hands-on it is and that I am on my feet all day. Reading and learning about things in the classroom are one thing but actually using your hands and seeing the work you do is incredible. I worked in Dr. Funk’s lab last summer and am super excited to have Andrew join in the iron catalyst project this summer.

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Hello! My name is Andrew Mahoney. I am a rising junior in the class of 2017, pursuing a Biochemistry and Molecular Biology degree with a double minor in Music and Neuroscience. This summer I am very excited to be in Dr. Funk’s research lab, working with Kathryn Fodale to develop new iron-based catalysts for oxidation-reduction reactions. This is my first summer doing research at Gettysburg. It has been a great experience so far, and I am very thankful that Dr. Funk and my labmates have been so supportive and put up with my shenanigans.

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Hello, my name is Rowan Meador. I am a rising senior at Gettysburg College and a Chemistry major and Math minor. I loved working in the lab the past summer, so getting the opportunity again was absolutely amazing. Being in lab is great because it is applying what was taught in lecture. This summer I am working on a different project than last summer, which I find neat because I will get exposed to more chemistry perspectives.

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Hey guys, my name is Tyler Sadka, a rising senior at Gettysburg College. I plan on graduating in May 2016 with a BS in Biochemistry and Molecular Biology and a minor in Business. I consider it a true privilege to be in Dr. Funk’s laboratory working on my own project in the company of Dr. Funk, Rowan, Andrew, and Kathryn, all very adept in chemistry. This is also my first summer doing chemistry research in Gettysburg, but so far, everything from the HHMI lunches to working up new reactions has been both an exciting and fulfilling experience.

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And finally Dr. Funk, the wonderful research advisor.

Iron Catalysis Kinetics (Kathryn Fodale and Andrew Mahoney)

We are continuing the research we worked on last year – developing iron-based catalysts that can do both oxidation and reduction reactions. Catalysts are important in chemistry because they increase the rate at which reactions occur, increase the yield of these reactions, and help to eliminate chemical waste. Catalysts that participate in oxidation and reduction reactions can be used in chemical manufacturing for both industrial and pharmaceutical purposes. However, the catalysts that are most commonly used now often contain heavy transition metals such as ruthenium, palladium, or rhodium. These metals, while great at what they do, are rare and therefore quite expensive. Because of this, it would be beneficial to develop cheaper, more sustainable alternatives, and as poor college students, we can relate to this goal. Another problem with using heavy metal-based catalysts is that they tend to be environmentally toxic. Because we are good chemists who care about our planet, our ultimate goal is to imitate the reactivity of these compounds but replace the heavy metals with iron, which is much friendlier to the environment and our wallets.

Last summer, our goal was to synthesize a bunch of different catalysts with slight structural modifications and test how well they catalyzed six different reactions. This summer we decided to go more in depth, and are studying the reactions more carefully. We are currently interested in the kinetics of each catalyst: how fast they are able to facilitate the conversion of one molecule into another. Because of this, our average day consists of hastily setting up a reaction (sometimes more than one!) in the morning. For the next hour, we scramble to fill up pipettes with cotton and silica gel (that stuff in shoe boxes that they tell you not to eat even though it looks delicious), take samples of our reaction every 15 minutes, and purify them by running each sample through the pipettes. After the first few hours of our day, things calm down a bit, as we then only take samples every thirty minutes, which gives us time to analyze our data, come up with plans for the next day, and clean up the silica gel that has inevitably spilled everywhere.

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Lactonization with Iron Catalyst (Rowan Meador)

Lactones, or cyclic esters, are found in beauty products, some antibiotics, and food additives, which means lactones are important industrially, since they are found in several everyday products. Lactones can made in a variety of different ways, and we are interested in the method that oxidizes diols with a precious metal catalyst. These precious metal catalysts are expensive and have a low natural abundance; therefore, if an iron catalyst could be used for this chemistry it would be a better alternative. This is because iron is the second most abundant metal in the earth’s crust, making it cheaper to access. Iron is also less toxic than the platinum group metals.

So far this summer, I have tested different iron catalysts in diol lactonizations. I am now focusing on optimizing the reaction conditions and testing several the catalysts ability to lactonize several different diols. I am also working on trying to make unsymmetrical diols to be tested as well.

Synthesis of an Organic Linker for Protein Isolation (Tyler Sadka)

The end goal of my project is to synthesize an organic linker that will bind and isolate proteins modified by O-GlcNAc, a post-translational modification on proteins involved in type II diabetes and Alzheimer’s disease. Bioorthogonal reactions currently employed for the detection and isolation of the O-GlcNAc-modified proteins include the Staudinger ligation and a [3+2] dipolar cycloaddition between alkynes and azides (sometimes referred to as “click chemistry”). While the click chemistry method often uses a copper catalyst, residual copper can hamper the detection process. Fortunately, this reaction can be done without the need of a catalyst by increasing the reactivity of the alkyne by straining it in an octane ring. This “copper-free click chemistry” is how I intend the linker to attach itself to the proteins via their GlcNAc modification. The linker will also be composed of two other components: an insoluble bead to bring the linker and proteins out of solution, and a coumarin core that will be used to separate the bead component from the rest of the linker using UV light.

The bead component has been purchased, and the coumarin core has been synthesized in three steps. For the past five weeks, I have been working on synthesizing the strained alkyne in the form of a BARAC (biarylazacyclooctyne). After performing the reaction a few times, and with help from Dr. Funk, I was successful in not only getting the reaction work, but also in making enough of the alkyne to experiment with coupling it to the coumarin core.

After coupling all three components, the linker will be sent to a branch of Novo Nordisk (located in Copenhagen, Denmark) to isolate GlcNacylated proteins from rat myoblasts. If the procedure is successful, I will continue looking in to more ways to increase the linker’s efficiency.

Summer Life on Campus

Living and working in Gettysburg during the summer is pretty sweet! We work 40 hours a week but then the rest of the time we have to ourselves, which is quite different from the school year. There is always something to do on campus– frisbee, $5 movies on Tuesday, game nights with friends, watching the sunsets on the battlefields, taking advantage of the volleyball court, and more! All in all we are having an amazing, chemistry-filled summer. Thanks for taking the time to read this post. Do great work!

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