Ali Altamimi ‘22 has achieved a rare feat: he’s developed his own molecule. The chemistry major synthesized and studied a novel guanidine-based ligand, as outlined in his thesis, “The Synthesis and Characterization of a Novel Chiral Guanidine-Based Four-Coordinate Tripodal Ligand DPI3tren.” He even had the opportunity to present this work at the June 2022 Central Regional Meeting (CERM) of the American Chemical Society (ACS).
Altamimi was inspired to pursue this as a thesis topic while taking “Superlab” with Professor and Chair of Chemistry Robert Scarrow during the fall of his junior year. It builds on work that was begun in the thesis of Diana Striplet ‘20.
“[Striplet] proposed that a future target four coordinate tripodal ligand (FCTL) of this sort should be made chiral to adequately isolate it for further characterization,” Altamimi said. Essentially, Striplet had synthesized a complex compound, though she could not turn it into a crystal to further study and characterize it, a step Altamimi kept in mind when designing the ligand he worked on.
Altamimi explained that Scarrow’s mentorship was integral in helping him design the project. Scarrow advised Altamimi to synthesize a molecule based on a ligand that was previously synthesized in the Scarrow lab in 2010, DIG3tren. This ligand was of particular interest due to its unique properties, and thus was even more desirable for Altamimi to study.
“[DIG3tren] mimicked the biological active site of a metalloenzyme and notably had the ability to act as a hydrogen-bond donor—a property that nature often uses in its reactions that chemists are interested in leveraging in functional synthetic molecules,” Altamimi said.
Along the way, Scarrow offered troubleshooting and training, as Altamimi familiarized himself with nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography-mass spectrometry (LC-MS).
The Scarrow lab was not the first lab Altamimi joined at Haverford, but rather the fourth. However, he’s glad he took the time to both find out which fields interested him and also gain experience in different fields, and he recommends that students do the same and explore different research interests.
Altamimi has already begun the next step in his career; he’s working at QPS, analyzing oligonucleotide therapies for pharmaceutical clients. In fact, in this work he uses techniques (LC tandem MS and high-resolution MS) that build on the LC-MS techniques he experienced in the Scarrow lab. Eventually, he is interested in pursuing a Ph.D. in analytical chemistry.
What are the implications of your research?
My thesis reported an optimized protocol for this synthesis, which current students in the Scarrow lab can ideally use to obtain the ligand at scale and form a coordination complex with a transition metal of their choice. My thesis provides them with some analytical data that they can compare their products and potential side reactions against. More broadly, this research has endeavored to explore new guanidine-based ligands, which are not explored as much as amines in the literature.
What is your biggest takeaway from your thesis?
My biggest takeaway from the project was an increased appreciation for analytical chemistry techniques and equipment, especially LC-MS, which combines physical separation and mass analysis for the identification of diverse compounds. My current associate scientist job is almost exclusively based on this skill, and I am discovering that I can orient my graduate studies around biological or environmental applications of this technique.
“What They Learned” is a blog series exploring the thesis work of recent graduates.