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Riboswitches are elements found in the 5’ untranslated region (5’ UTR) of primarily bacterial mRNAs that bind specific intracellular metabolites called ligands. These ligand-riboswitch interactions function to promote gene expression (upregulation) or inhibit gene expression (downregulation) as a result of the subsequent conformational changes the riboswitch undergoes. RNA molecules have in recent years been gaining attention as antibiotic targets due to the rising crisis in antibiotic resistance. The xpt riboswitch is a guanine response riboswitch involved in purine biosynthesis and transport pathways, which inhibits purine gene expression in the presence of bound guanine. Previous preliminary work in the Jain lab has shown that guanosine, an analog of guanine, inhibits gene expression with greater efficiency than the natural ligand when bound to the xpt riboswitch. This study focuses on using the guanosine structure as a scaffold for exogenous active antibacterial compounds starting with N2-acetyl-6-hydroxylaminoguanosine (SK4). By introducing potential hydrogen bond donors and acceptors at the C2 and C6 positions of the purine ring we hope to achieve high binding affinity with efficient in vivo activity at the xpt purine riboswitch.
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Gindinova, Katherina, "Synthesis of Potential Antibacterial Compounds Using Guanosine as a Structural Scaffold" (2016). Senior Projects Spring 2016. 19.