A research collaboration between the Chemical and Pharmaceutical Science group and a group of students was published in the European Journal of Organic Chemistry.
Date: 7 October 2022
Dr Bhaven Patel, a reader in Organic Chemistry and course leader for Pharmaceutical Science, collaborated with Dr Kevin Devine and Dr Daniel Sykes, colleagues from the Chemical and Pharmaceutical Science group, to work with studentswith students to publish a piece entitled ‘Room Temperature DBN Initiated Phospha-Brook Rearrangement of α-Hydroxyphosphonates to Phosphates.’
The publication originated from an undergraduate research project by student Aleema Iqbal, who was trying to design anti-malarial drugs. During the project they observed an unexpected phospha-Brook rearrangement taking place.
In the summer of 2021, Muskaan Mahandru-Gill obtained an Undergraduate Research Bursary from the Royal Society of Chemistry to continue to develop this project further. She was able to optimise conditions and make a range of novel phosphates, which have been extensively studied as they play important roles in many physiological processes.
The project was completed this summer by Francesco Spiedo and Margarita Damai, who wanted to gain research experience. They were trained by Dr Bhaven Patel and took the lead in changing different variables to achieve the best results for the conversion taking place.
Margarita was exited for the opportunity to work on the project. "Getting involved in this project was a one-of-a-kind experience for me. I had no prior experience in a lab, but I was always keen to get involved. When I expressed my willingness to participate to Dr Patel, he kindly accepted to train and teach me the science behind the research mechanism. It was exciting to work in an advanced research laboratory, getting to use cutting-edge machinery and most importantly learn a range of new techniques."
Working on the project gave Francesco a glimpse of a future career in chemistry. "Working on this project with Dr. Bhaven Patel has given me the opportunity to have a hands on look on what my future career will look like. Working alongside a research pioneer has
also helped me develop a new set of skills at early stages of my studies. The chance to work unsupervised, independently in the lab and make decisions was a thrilling and totally novel experience for me."
Dr Patel underlined the importance of the project. “Organophosphates are very important in physiological processes. In this project we developed a new way to produce phosphate esters in excellent yields from α-hydroxyphosphonates using a phospha-Brook rearrangement. This reaction normally requires heating and the students have taken the lead to find conditions for the reaction to take place at room temperature using 1,5-diazabicyclo(4.3.0)non-5-ene (this has not been done before).”
He also emphasised the importance of involving students in research like this, “it was a wonderful opportunity for the students. They researched how the reaction took place and worked with the NMR technician to conduct mechanistic studies, using low temperature 31P-NMR. They were able to propose that the reaction took place via formation of a three membered oxaphosphirane intermediate. This was based on previous studies but this is the first time that that this was evidenced experimentally.”