The Pathway to BMOPP

Posted July 10th, 2011 at 8:38 pm.

Abstract: Hannah Gilbert

Mentor: Dr. Sharon Burgmayer

This research will deal mainly with pterin chemistry in relation to the molybdenum cofactor in molybdenum-containing enzymes. As molybdenum enzymes are required within every living organism and as there is little study in the field of molybdopterin chemistry, it is very relevant to investigate the character of molybdenum pterin dithiolene chemistry. The immediate goal will be to replenish a depleted supply of 6-chloro pterin. 6-chloro pterin is the starting material for 2-pivaloyl-6-chloro-pterin synthesis. “Piv-Cl-pterin” is used to make BMOPP, a main focus of molybdenum pterin dithiolene chemistry. Increasing the scale of the pterin reaction will be done by carefully adjusting a previously successful 4-step synthesis that uses more efficient starting materials. The first step, shown below, produces pterin from hydroxy-triaminopyrimidine. Step two adds a directing group that is critical in step three which utilizes the directing group for chlorination specifically at C6. There are significant challenges in synthesizing 6-chloro-pterin, particularly the complicated neutralization step four where most of the product can be lost while adjusting the pH due to insufficient precipitation. This step will be evaluated and closely examined to try to ensure a maximum yield of 6-chloro-pterin. While it is very difficult to evaluate the purity of pterin solids, the techniques used for characterization will include, but not be limited to, NMR and IR spectroscopy.


Filed under: 2011,Burgmayer, Dr. Sharon,Gilbert, Hannah by Michelle Han

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