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.

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. 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. 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. 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. 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. 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. 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