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Postgraduate Research @ Mayo Clinic Jacksonville

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Postgraduate Research @ Mayo Clinic Jacksonville

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Here is a brief overview of some of my work at Mayo Clinic Jacksonville, where I worked in the Organic Synthesis Core Facility for the little over two years between my undergraduate education and graduate school.

Here is a brief overview of some of my work at Mayo Clinic Jacksonville, where I worked in the Organic Synthesis Core Facility for the little over two years between my undergraduate education and graduate school.

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Postgraduate Research @ Mayo Clinic Jacksonville

  1. 1. Postgraduate Research Mayo Clinic Jacksonville Organic Synthesis Core Facility Jacksonville, FL Diagnostic Tools and Therapeutic Candidates for Muscular and Neurodegenerative Diseases Sean Owen Clancy, Ph.D. All material contained within is copyright © 2006 Sean Owen Clancy and / or the respective institutions.
  2. 2. Medicinal Chemistry O OCH3 O O Boc NH N H N N O N NH H H O • Caffeine Precursors & Derivatives for HPLC Standards • Modified Tryptophan Cbz OH HN HO N HO OH O N HO OH O C O • Inositol, Muscle and Nerve Boc N Research Tools N H OEt Si • Cytosine, Peptide Nucleic Acid O tBoc-Protected Monomers HO O HO OH • tBoc and Fmoc Chemistry with • D-Lyxose & Other Carbohydrate Derivatives Peptides and Peptide Nucleic Acids Mayo Clinic Jacksonville, Synthetic Organic Chemistry Core Facility, Neurochemistry Research
  3. 3. Mayo Clinic Research Organic Synthesis • Carbohydrate and inositol chemistry • Peptide nucleic acid (PNA) monomer synthesis and oligomer synthesis • Synthetic amino acids and proteins Characterization • NMR (proton and carbon) • FT-IR • GC/MS • Polarimetry Applications • Drug candidates for neurodegenerative and other diseases Mayo Clinic Jacksonville, Synthetic Organic Chemistry Core Facility, Neurochemistry Research
  4. 4. Mayo Clinic Research OMe O OH OCH3 OH O HO HO OH O CSA, DMF H3CO cat. camphorsulfonic acid H3CO HO O OMs OMs OH O O OH HO OH DMF, 60 deg C O OH OH O + O O O H3C S Cl NaH,PMB-Cl O O O O DMF, 0 deg C to r.t. O O OMs O OMs OH TEA, CH2Cl2 OPMB 0 deg C LAH, THF O 0 deg C to r.t. 24 h OH O O O H3CO BBr3, CH2Cl2 O HO O OMs Swern O O LiBH4 O OH O HO 0 deg C to r.t. O O oxidation THF HO OMs O OH O O O OH OPMB OPMB OPMB O Inositol chemistry • Used in muscle and nerve research. • Inositol starting material is a side product of rubber industry, so it can be acquired at a cheaper price from Malaysia. Mayo Clinic Jacksonville, Synthetic Organic Chemistry Core Facility, Neurochemistry Research
  5. 5. Mayo Clinic Research O i.) di-t-butyldicarbonate, CH2Cl2, 20 h, r.t. H NH2 Boc N H2N N OEt ii.) BrCH2O2Et, CH2Cl2, r.t. H Cbz Cbz HN NH2 O HN DCC / DhbtOH N O Cl N N DMF / DCM O N O N N H O CO2H N H Cbz HN i.) BrCH2CO2CH3 N ii.) NaOH (aq.) O N Cbz HN O C O N Boc N O N N OEt H CO2H Peptide nucleic acid monomer synthesis • Peptide nucleic acid monomers were commercially available, but it was determined that it would be more cost effective if I made them. We had to change the solid-state synthesis a little to accommodate a different protective group chemistry. • I wrote a protocol that was used to aid grant and patent progress for primary investigator, Elliott Richelson, M.D.. Mayo Clinic Jacksonville, Synthetic Organic Chemistry Core Facility, Neurochemistry Research
  6. 6. Knowledge, Skills, and Abilities Enhanced or Obtained via this Research • Design and synthesis of: small molecule organics, in the form of carbohydrates, peptides, peptide nucleic acid monomers and oligomers, inositols, synthetic amino acids, etc.. • Characterization of materials through a variety of techniques: NMR, gas chromatography- mass spectrometry, elemental analysis, absorption spectroscopy, Fourier transform infrared spectroscopy, etc.. • Purification of materials via: column chromatography, preparative thin layer chromatography, preparative high pressure chromatography, ambient pressure and vacuum distillation, reprecipitation, and recrystallization. • Structure-property / structure-function relationship studies. Mayo Clinic Jacksonville, Synthetic Organic Chemistry Core Facility, Neurochemistry Research
  7. 7. Acknowledgements Mayo Clinic Jacksonville Supervisor Research Group Abdul H. Fauq, Ph.D. Chewki Ziani-Cherif, Ph.D. Feng Hong, Ph.D. Collaborators Elliott Richelson, M.D. Terrone L. Rosenberry, Ph.D. Funding was provided by: • Mayo Foundation • National Institutes of Health • U.S. Public Health Service Mayo Clinic Jacksonville, Synthetic Organic Chemistry Core Facility, Neurochemistry Research

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