The Synthesis of DoubleBond Conjugated Hydroxamic Acids 异羟肟酸的共轭双键的合成.pptVIP

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The Synthesis of DoubleBond Conjugated Hydroxamic Acids 异羟肟酸的共轭双键的合成.ppt

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The Synthesis of DoubleBond Conjugated Hydroxamic Acids 异羟肟酸的共轭双键的合成

Synthesis, Characterization and Iron-Acquisition of Hydroxamic Acid Derivatives -Functional studies based on the subunits of amphiphilic siderophores Linda M. Johnson University of North Carolina at Chapel Hill Class of 2003 Dr. John T. Groves/ Minkui Luo Princeton University May 6, 2004 Mercer County Community College Iron – An Important Element 4th most abundant element in the world An important nutrient for the body. Helps with growth and development in the body, especially in children. Iron is forever cycled from a liver storehouse in a protein called ferritin. The Paradox of the Limited Abundance of Iron Siderophores Small weight compounds that have a high affinity for Fe (III). Help with Iron Transport. Three subunits of siderophore’s chelating groups. A Common Strategy of Bacteria --- Iron-Delivery Shuttle, Siderophore Water-phase Iron-acquisition Kinetic of Citrate-based Amphiphilic Siderophore Purpose of Experiment To examine and compare the structures of siderophores’ sub-units-hydroxamic acids. To understand how hydroxamic acids facilitate the iron chelating process of siderophores by measuring their iron-acquisition rate. ? Synthesis of N1-BOC propane diamine Synthesis of Compound II III Synthesized Boc-protected amine Use Flash Column Chromatography (FCC) to help separate compound. Perform Thin Layer Chromatography (TLC) to help locate the final product. Check purity of compound with 1H-NMR. Five substrates used to react with the amine: Acetyl Chloride Cinnamoyl Chloride Butyryl Chloride Crotonyl Chloride Hydrocinnamoyl Chloride Procedure of Analog Synthesis Performed test reactions with each halide. Check TLC and take 1H-NMR for each reaction. Once reaction is successful, upscale amount of material for future experiments. Reaction Between Amine and Acetyl Chloride Equation: Results: 1st attempt: No distillation or either substrate nor solvent. Some reaction occurred, but it was not complete, even after adding 10% base to hel