Nicholas Reid Awarded NSF Summer Research Experience for Undergraduates


Nicholas J. Reid stands beside his work station in Dr. Roger Laine's lab.

LSU Biological Sciences undergraduate student, Nicholas J. Reid gained acceptance to the prestigious NSF Summer Research Experience for Undergraduates (REU): Integrative Biology at UC Berkeley, from Molecules to Ecosystems. This 10-week program has only a 4% acceptance rate and is designed to expose participating students to core Molecular, Cell, Developmental, Evolutionary, and Ecosystem Biology.

According to the National Science Foundation (NSF), participants will work under the direct guidance of a UC-Berkeley faculty mentor and will gain first-hand research experience and training in state-of-the-art research facilities while working on individual projects. Professional development workshops and interactions with faculty, postdoctoral fellows, graduate students and UC-Berkeley undergrads will familiarize participants with the graduate school experience, including the application process, what to expect in graduate school and the career possibilities it opens up.

In the course of the program students will prepare a short scientific paper on their project. During the last week, a mini-symposium will permit the participants to share their accomplishments.

Reid is an undergraduate student whose interest in carbohydrate chemistry led him to work in Dr. Roger Laine's and Dr. Justin Ragain's labs for the past four semesters while majoring in Biochemistry.

According to Dr. Laine, Reid’s project in his lab was extracting, isolating and purifying Betulin from birch bark powder for the purpose of finding an inexpensive oxidation to Betulinic Acid, an antimelanoma drug and potent anxiolytic. There was both a primary and secondary alcohol group in Betulin, and the goal of Reid’s work was to find a method for inexpensive selective oxidation of the primary alcohol to betulinic acid.

Birch bark is about 20% betulin, a rich source for betulinic acid if an inexpensive oxidation were developed.  An oxidation of both the primary and secondary hydroxyls is easy, but reduction of ketone gives 2 epimers, difficult to separate. Protection, deprotection of the secondary hydroxyl is too expensive. Laine directed Reid to look into carbohydrate chemistry methods where the uronic acids are made to find potential oxidation methods. 

Reid started out with an interesting observation from the literature that sucrose was used to reduce manganese resulting in oxidation of the primary alcohols, so he did a number of experiments with sugars first to see if he could effect a primary oxidation with this simple method. He used GC/MS of the derivatized products to look for yields. 

Laine said, “Reid was an extremely active researcher in the lab, always excited, wanting discussions, meanwhile making the highest grade in his first Organic Chemistry, and maintaining a high average with heavy load. He is one of the brightest students I have had in the lab, and worked with me for three semesters.”

Eventually Reid explored a number of methods to make betulinic acid, and in the fall of 2016, Laine directed him to a postdoc researcher who was doing oxidations to synthesize nootkatone in his lab. Reid and the researcher eventually decided that modification of a method using TEMPO was the best method to make the acid. 

This semester, Reid, having become interested in carbohydrate chemistry from working in Laine's lab, moved to Justin Ragain's lab in Chemistry where he is making protected sugars to assemble into oligosaccharides. 

According to Laine, “This guy will have a great future, voracious reader, thinker, ambitious, hard working, attentive. When scientists come to visit, I often invite him to the get-togethers to give him a broad exposure.”

Roger Laine’s lab has projects ranging from biology to mass spectrometry methods development. He is a carbohydrate biochemist by training with a major focus on using mass spectrometry as a tool. He has also been involved with a number of start-up companies, and most work in his lab is now focused on patentable practical research. Laine exposed Reid to a lot of the tools and techniques in use by the Laine’s four startups, preparing him well for a seemingly bright future in biochemical research.