Synthesis of Amino Acid Surrogates Using Buchwald Hartwig Amination
Mahmuda Rahman, Chemistry, Gregory O'Brien, Independent Study, Christa Baker, Chemistry and Victoire G Karambizi, Biology
Faculty Mentor: Professor Sujit Suwal, Chemistry
Buchwald–Hartwig amination (BHA) is the palladium-catalyzed coupling of amines and aryl halides. The synthetic utility of BHA stems primarily due to the shortcomings of other aromatic C-N bond formation methods, that often suffer limited substrate scope and functional group tolerance. BHA is widely used in organic synthesis to create a variety of molecules that have medicinal and pharmaceutical essence. In this prospect, we explored BHA towards restructuring several heterocyclic halides into highly functionalized amino acid surrogates that could fuel syntheses of novel peptidomimetics having better pharmaceutical indices. Most importantly, these building blocks allow us to design conformationally constraint oligomers that are cell-permeable, proteolytically stable and potentially offer high-affinity protein ligands. To date, we are successful in synthesizing more than a dozen amino acid surrogates. Currently, we are optimizing solid phase syntheses of hybrid peptides/peptoids that contain surrogate amino acids. Also, we are exploring the MS-based sequencing method that can deconvolute subunits within the oligomers.
Rahman, Mahmuda; O'Brien, Gregory; Baker, Christa; and Grace-Karambizi, Victoire, "Synthesis of Amino Acid Surrogates Using Buchwald Hartwig Amination" (2020). Physical Geography and Sciences. 22nd Annual Student Research and Creativity Conference. SUNY Buffalo State.