Synthesis of Hydroxyarginine and Precursor Guanidinylating Agent

Andrew Beszhak, “Synthesis of Hydroxyarginine and Precursor Guanidinylating Agent”
Mentor: Alan Schwabacher, Chemistry & Biochemistry

Keto-hydroxyarginine is a precursor to Endurcididine, an oxidized arginine found in potent antibiotics. A The Mpp family of enzymes transforms these arginines into enduricididines. Enduricididine is a non-proteogenic amino acid, one that isn’t encoded directly by the genetic codes of any organism, rather one generated through post-translational modifications of mRNA molecules. This is to say, if you want to study it, you have to make it. Overall, investigating these reactions involving arginine, MppP, MppQ and MppR will allow for a formal understanding of the biosynthesis, kinetics and mechanism of these molecules, possibly resulting in applications in other antibiotic syntheses. Reagents, like Ethyl nitroacetate and Di-Boc Pyrazole are needed to synthesize precursors to the Mpp pathway. Unfortunately, these compounds are either not readily available, expensive, or both. For these reasons, the independent synthesis of these compounds is paramount.

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