Poster abstracts
Poster number 151 submitted by Melanie Clawson
Semi-enzymatic Synthesis of Pseudouridine
Melanie Clawson (Department of Biological Science, Southern Illinois University Edwardsville), Tristan Sanford (Department of Chemistry, Southern Illinois University Edwardsville), Andrew Riley (Department of Chemistry, Southern Illinois University Edwardsville), Kylie Raasch (Department of Chemistry, Southern Illinois University Edwardsville), Ridwan Oyebamiji (Department of Biological Science, Southern Illinois University Edwardsville), Mina Sumita (Department of Chemistry, Southern Illinois University Edwardsville)
Abstract:
Modifications of RNA molecules have a significant effect on their structure and function. One of the most common modifications is pseudoruidine (Ψ) which isomerizes from uridine. Recently, pseudouridine is in high demand due to the COVID-19 pandemic because a derivative of pseudouridine (N1-methylpseudouridine) has been used for the development of mRNA vaccines against SARS-CoV-2. However, organic synthesis of pseudouridine has been challenging because of the stereochemistry requirement and the sensitivity of reaction steps to moisture. Herein, a semi-enzymatic synthetic route is developed for the synthesis of pseudouridine using a reverse reaction catalyzed by a pseudouridine monophosphate glycosidase. This synthetic route has fewer steps and high yield production of pseudouridine
References:
Huang, S.; Mahanta, N.; Begley, T. P.; Ealick, S. E. Pseudouridine Monophosphate Glycosidase: A New Glycosidase Mechanism. Biochemistry 2012, 51 (45), 9245–9255.
Preumont, A.; Snoussi, K.; Stroobant, V.; Collet, J. F.; Van Schaftingen, E. Molecular Identification of Pseudouridine-Metabolizing Enzymes. J. Biol. Chem. 2008, 283 (37), 25238–25246.
Riley, A.T.; Sanford, T. C.; Woodard, A. M.; Clerc, E. P., Sumita, M. Semi-enzymatic Synthesis of Pseudouridine. Bioorg. Med. Chem. Lett. 2021, 44, 128105
Keywords: RNA modification, modified nucleotide synthesis, pseudouridine