Making Headway!

This last week has been filled with new experiences and exciting lab results, but as a result I have neglected my blogging duties. Don't worry folks, to repay for my delay I will be sure to make this post especially long and detailed. Haha! I'm only kidding. I will do the best to recap the week in a short yet descriptive manner.

My time spent in the lab was filled with new experiences. Last Monday, I worked in another lab and assisted a graduate student in completing an esterification reaction. For past blog followers, this was the esterification of hibiscus acid that I mentioned before. The synthesis was exciting and fairly straight forward. My tortoise shell goggles made their feature debut along with a brand new lab coat and some fancy blue nitrile gloves. After looking at nuclear magnetic resonance readings we decided we had made the product; unfortunately, we also discovered an impurity. The graduate student told me he would work on some purification ideas and get back to me. He found a way to get rid of the impurity, but he accidentally undid our reaction in the process. Luckily, we had plenty of starting material, and Ed, the graduate student I worked with, offered to redo the reaction over the weekend. Although I would have enjoyed delving into some more organic chemistry, I had already made plans for the weekend.

The time had come to delve even deeper into the south! My roommate Austin is from a suburb of Birmingham, Alabama so she was kind enough to take us with her to visit her family. Austin's family owned a boat a little over halfway between Nashville and her home. We met Austin's dad at the lake and he was kind enough to take us out for the day. It was a blast! We went tubing, laid out on the dock, and felt the wind whip through our hair as we cruised around the lake. The lake itself was gorgeous. There were tons of homes with eye catching architecture planted all around the lake and deep green trees covered the shoreline. We were so fortunate that the weather was nice while we were there. The whole way driving to the lake, Austin had to battle against a torrential rain storm, but about fifteen minutes out from the lake everything stopped. Not only was it not raining when we arrived, it didn't rain the whole time we were there! Are we lucky, or what? To top it all off, we spent the night at Austin's home and her mother made us a gourmet dinner with peach cobbler for dessert. It was like a little piece of heaven! I cannot thank Austin's family enough for all their hospitality.

Sadly, the weekend did have to come to an end, but so far this week in lab has been very productive. I finished the ORD and ECD measurements of one of the compounds and I will begin VCD measurements tomorrow!

I would like to wish a Happy Father's Day to all the dad's out there! I hope everyone is enjoying the weather back home. I hear the the sun has been shining in Colorado. I look forward to sharing with you all again soon!

Getting My Hands Dirty

They have actually allowed me to touch a couple of the instruments! On Friday I conducted an ECD scan and some ORD measurements on a compound called hibiscus acid disodium salt. This compound is very similar to the compound that I will be doing my project on this summer. Both molecules have two carboxylic acid groups. In the disodium salt molecule, the hydrogens on the carboxylic acids have each been replaced with a sodium molecule. In the molecule I am studying I will conduct an esterification to convert the hydrogens into methyl groups. The figure below shows the compound I will be working on this summer. The boxed hydrogens are the ones that are being replaced. (I copied the image from a Science Direct article called Chiral gamma-butyrolactones related to optically active 2-hydroxycitric acids) The purpose of this esterification is to protect the the molecule from undergoing reactions with any of the solvents used that would result in configurational changes.

Tomorrow, I will begin my hands-on experience with the VCD instrument. Liquid Nitrogen here I come! The photo above, taken by my mentor at the conference, displays the VCD instrument. The white cylinder contained within the plastic box is a dewar. (I'm sorry that it is kind of difficult to see.) Liquid nitrogen is poured into that dewar and used to cool the detector for up to 12 hours. On Tuesday, I will be going to Dr. Rizzo's lab to work with one of his post doctors. With the post doctor's close supervision, I will be conducting the esterification reaction. From what I understand the esterification is a fairly standard procedure, but one of the compounds being used is highly flammable and a scratch in the glass could potentially cause the compound to spark. Who ever said science wasn't exciting!

This weekend was jam packed with country music and free stuff. The CMA Country Music Festival was held in Nashville this weekend and it was quite the event. There are multiple stages where small name bands put on free concerts all day and at night if one had tickets they could attend the big name concerts held at LP Field. Us poor REU students decided to stick with the free concerts and the free goods. All day long local vendors set up stands down 2nd street handing out free samples. I received dog treats, Manwich sandwiches, and everything in between. I also saw Joe Nichols, a fairly big name country star that I like, play on one of the free stages. My boots made their premiere on Friday night, but I decided not to wear them on Saturday or Sunday. Partly because they still need to be broken in, but mostly because it was so warm! To try to combat the heat, the festival organizers placed mister statations throughout the town. Basically, you stand under a white tent and have mildly cold water lightly sprayed all over you for as long as you desire. It may not sound enticing now, but in ninety degree weather it feels like the only escape!

Well, tomorrow it's back to the grind. I'm looking forward to going over some calculaitons with my mentor and learning how to use the VCD instrument. It's going to be an exciting week. Hope everyone enjoys their weeks wherever they are. Happy birthday to all my family members! My mom's and my brother-in-law's birthday was last Monday, my twin cousins turned 20 today, my dad and both my sisters will be celebrating their birthdays tomorrow, and my nephew EJ will be turning 2 on Tuesday. There are a few more family birthdays in June, but I'll be sure to mention them as the arrive. I'm sorry I can't make all the celebrations and I love and miss you all!

Mission Completed!

That's right ladies and gents! I have officially found a pair of cowgirl boots. My friends Nichole and Mary rode with me through the rain and the traffic to get to our boot destination. The shopping excursion made for a hectic afternoon, but it was worth it! Both Nicole and I found boots that we liked for the low price of $43. I realize that spending $43 on a souvenir item seems a bit absurd, but, considering other boot prices, I feel like I made out like a bandit.

Although uncovering the perfect pair of boots was exciting, I was part of far more interesting activities this week. Today was the final day of the three day chirality workshop hosted by my mentor, Dr. Prasad Polavarapu. The focus of the conference was discussing the different instruments used to determine the absolute conformation of molecules: Optical Rotary Dispersion, Electronic Circular Dichroism, Vibrational Circular Dichroism, and Raman Optical Activity. There was also a presentation on the Chiral HPLC and Supercritical Fluid Chromatography instruments used at Vanderbilt for isolation of enantiomers. Given my background in HPLC, I was most intrigued by the HPLC demonstration. I never realized how much could be accomplished with an HPLC and I was given advice about how to better my own results. (Dale, I thought you would be glad to hear that the expert I spoke with here believes that the water pump on the instrument is most likely faulty. I will have to run some tests when I get home because I didn't get the chance before I left. Hopefully, I will be able to eliminate the drift in my chromatograms).

Due to my lack of knowledge about circular dichroism I found some of the lecture material a little difficult, but the instrument demonstrations were really impressive. Many people from industry attended the conference and told us a bit about how far their instruments had come. The Vibrational Circular Dichroism (VCD) instrument is fairly new to the market. The instrument we have in our lab was the second instrument ever made and it was installed in June of 1998. In 2005 the instrument was updated with the addition of a second photoelastic modulator. The instrument is now considered a Dual PEM VCD. PEM is simply an acronym for photoelastic modulator. Having two PEM's rather than one reduces the number of artifacts and the background noise. I feel very fortunate to have the opportunity to work with such advanced instruments and I am sure I am going to learn a lot.

I am also looking forward to learning about computational methods. An important facet of the conference was discussing the quantum mechanical calculations that are being used to predict molecule conformations. All spectra from the instruments measured are compared to computationally produced results in order to identify the absolute configuration. If the experimental and the computational results correspond well, a correct configuration has likely been uncovered. It is important to mention that one should never use just one method for measuring chirality, but instead use multiple instruments to increase the possibility for correct identification. This summer I will have the opportunity to be trained on two computer programs called Linux and Gauss View and I will be able to use the super computer on campus for calculations.

I truly feel blessed to be exposed to so many new things. Different comments made at the conference made me realize that Dr. Polavarapu is truly on the cutting edge of chirality studies. He also has connections with people from various industries and countries. Companies like Jasco, Biotools, Amgen, and Hinds Instruments were all represented at the conference and there were attendants from France, India, Poland, and Guatemala, just to name a few. Having Dr. Polavarapu as my mentor means that I will be working with the best! As I learn more about the instruments I will try to tell you all more. Some of the information is difficult to explain without diagrams, but I'll do my best. Maybe I can attach a diagram to my blog. I still haven't figured out all the fancy tricks. Either way, I'll keep you all updated. Thanks for reading!

P.S. Sorry for the lack of pictures. I forgot my camera cord at home, but luckily Lisa has offered to ship it to me! I'll try to post some pictures soon!

Enjoying the sites!

One of the great things about joining an REU program is that the majority of programs have special activities planned for you to do outside of the lab. This weekend we went on a five mile canoeing trip down the Duck River. It was gorgeous! The river is surrounded by trees and the water is cool, but not freezing. My roommate Austin and I rode in a boat together. We enjoyed all the sights, but we also plotted some fun of our own. We spent a large portion of the trip splashing our fellow program members and attempting to tip their canoes. As a result, we fell victim to being tipped twice ourselves. Unfortunately we did loose a thing or two to the 'river gods', but the laughs were worth it. Our group also enjoyed the opportunity to eat lunch on the beach, swim around in the water, and play on a rope swing.

Although the trip was tons of fun, all the splashing and boat flipping left me feeling rather exhausted. When we got back I took a nice long nap and woke up just in time to enjoy the night life of Nashville. A few of the girls and I went down to 2nd Avenue and saw all the sights. There were tons of bars with live music, various street performers, and lots of shops that are named after country icons. One woman we saw was playing spoons. I had always heard of such a talent when I was a child and was banging my spoon on the kitchen table, but I had never seen the act in real life. I can say without a doubt that this woman's spoon antics brought much more musical joy than my attempts as a child.

Even though we enjoyed the sites and getting a better feel for Nashville, we went to 2nd Avenue for a particular purpose: buying cowgirl boots! The CMA music festival is next weekend and a couple of us girls think it would be fun to have a pair of boots to wear. Unfortunately, we did not realize that authentic cowgirl boots cost about $100 dollars and that's only if they are on a really good sale. We have decided to refine our boot search and settle for boot knock offs. We are going to go to a nearby mall this afternoon to see what we can find. I'll be sure to keep you updated on the mission. Oh, and I'll try to let you know about the research some as well. I am going to a three day chirality workshop this week. I am really excited to learn all about the instruments and meet people from various colleges, labs, and industries.

Hit the ground running...

Or more jogging in my case. I began working in the lab this week and so far so good. On Tuesday we had orientation with our program coordinator. We were given tours of the mass spec and NMR facilities and we were given a lecture on lab safety. I have to admit that I was a little disappointed that they didn't present the well-known display "Mary didn't were her safety goggles...now she doesn't have to". I've always thought that one was a classic. One of my good friends suggested that I use that quote and draw an accompanying picture if I was ever at a total loss on a test. Luckily, I haven't had to pull that out of my bag of tricks just yet.

I started working in the lab on Wednesday. I say that I am traveling at a jogger's pace because as of know I am just familiarizing myself with some reading material. I am going to be doing a lot of work with a computer program called Linux this summer so I have spent the majority of my days reading over the manual and practicing the various command keys. This is certainly a new area of research for me and it is going to take some getting used to.

The drugs that we will be testing this summer have already been synthesized. My project will be focused on a compound called hibiscus acid. I am going to wait to stick my foot in my mouth and do some more research before I give you all more details about the compound. What I do know is that for one of the testing methods we will have to conduct an esterification reaction. Admittedly, my organic chemistry is a little rusty, but my understanding is I will be reacting the hibiscus acid with methanol in the presence of a catalyst like sulfuric acid. I think this is going to be my chance to make my goggles shine so I plan to make the most of it!

Other than that I will be working with the OCD, VCD, and ECD instruments. In all these acronyms CD stands for circular dichroism and the O stands for optical, V stands for vibrational, and E stands for electronic. Once again I need some more learning time before I explain all of these instruments to you, but what I do know is that one of them requires liquid nitrogen. Jarral, I wish you could see the size of the dewars (containers for liquid nitrogen) they have here. If I break one of those I will go down in Vanderbilt history! They will make a plaque that says "Emily Donahue-The Most Expensive Undergraduate We've Ever Employed". I am not sure that is the lasting mark I hope to make here.

Prasad, my mentor, is holding a chirality workshop on Monday-Wednesday next week that I will be attending. Once that is over, my jogging days will have ended. I am excited to dive in and start working on the project. I'll be sure to explain all the details once I figure them out myself.