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.
The big topic of the last few years, the use of small organic molecules to catalyse enantioselective transformations. This lecture will start with proline before moving on to some of MacMillan's contributions to this field and, finally, finish with hydrogen bond catalysts and Brønsted acids.
Hemicellulose extraction from wood OSB strandsroryjara
Extraction of wood components from OSB strands using hot water. A composition of the liquid phase (extract) is given for different extraction conditions. Mechanical properties of OSB panels made with the extracted wood are compared with standard panels.
The big topic of the last few years, the use of small organic molecules to catalyse enantioselective transformations. This lecture will start with proline before moving on to some of MacMillan's contributions to this field and, finally, finish with hydrogen bond catalysts and Brønsted acids.
Hemicellulose extraction from wood OSB strandsroryjara
Extraction of wood components from OSB strands using hot water. A composition of the liquid phase (extract) is given for different extraction conditions. Mechanical properties of OSB panels made with the extracted wood are compared with standard panels.
Self explanatory really, this lecture looks at chiral auxiliaries. We will concentrate on oxazolidinones in alkylations, aldol reaction and the Diels-Alder reaction. There will be a couple examples of other auxiliaries.
A pharmaceutical Chemist shares a view of organic chemistry and his role preparing enantiomeric drugs for clinical trials. Dr. Welch is also on the Titan Explorer team looking for signs of life on other planets
BITS - Introduction to Mass Spec data generationBITS
This is the first presentation of the BITS training on 'Mass spec data processing'.
It reviews the basic concepts of mass spectrometry data generation.
Thanks to the Compomics Lab of the VIB for contribution.
Finishing oxidation by looking at the Baeyer-Villiger reaction and then turning our attention to reduction. Once again we will see the usual suspects with a who is who of hydride sources.
A look at epothilone A as it includes examples of many different forms of asymmetric synthesis. Also includes a little bit about ring-closing metathesis.
Gives an introduction to total synthesis and why we do it (which reminds me, I must add a picture of Everest, as I think the fact that 'it is there' is the main reason for most syntheses). Then to introduce the topic with a reasonably simple synthesis, we will look at an example of the synthesis of Tamiflu.
Palestra realizada pelo Instituto de Estudos Avançados da USP, Polo Ribeirão Preto. Mais informações: http://www.iearp.blogspot.com.br/2012/08/eletronica-organica-uma-nova-fronteira.html
Self explanatory really, this lecture looks at chiral auxiliaries. We will concentrate on oxazolidinones in alkylations, aldol reaction and the Diels-Alder reaction. There will be a couple examples of other auxiliaries.
A pharmaceutical Chemist shares a view of organic chemistry and his role preparing enantiomeric drugs for clinical trials. Dr. Welch is also on the Titan Explorer team looking for signs of life on other planets
BITS - Introduction to Mass Spec data generationBITS
This is the first presentation of the BITS training on 'Mass spec data processing'.
It reviews the basic concepts of mass spectrometry data generation.
Thanks to the Compomics Lab of the VIB for contribution.
Finishing oxidation by looking at the Baeyer-Villiger reaction and then turning our attention to reduction. Once again we will see the usual suspects with a who is who of hydride sources.
A look at epothilone A as it includes examples of many different forms of asymmetric synthesis. Also includes a little bit about ring-closing metathesis.
Gives an introduction to total synthesis and why we do it (which reminds me, I must add a picture of Everest, as I think the fact that 'it is there' is the main reason for most syntheses). Then to introduce the topic with a reasonably simple synthesis, we will look at an example of the synthesis of Tamiflu.
Palestra realizada pelo Instituto de Estudos Avançados da USP, Polo Ribeirão Preto. Mais informações: http://www.iearp.blogspot.com.br/2012/08/eletronica-organica-uma-nova-fronteira.html
This pocket guide is intended for physician's and medical professionals who are referring infants and toddlers, birth up to age 3, to early intervention services through Early On Michigan. For more information visit: 1800EarlyOn.org.
LICCs are local planning and advisory bodies for the local Early On system, established through the 56 ISDs in Michigan. LICCs mirror the mandated MICC in concept and allow for involvement of parents, agencies, organizations, and individuals necessary to develop and maintain a coordinated early intervention service system. The role of an LICC is to advise and assist the intermediate school district in matters related to Part C of the Individuals with Disabilities Education Act (IDEA), Early Intervention Program for Infants and Toddlers with Disabilities: Final Regulations. In Michigan we call this program Early On. LICC activities include: fostering interagency collaboration and information sharing, disseminating public awareness and other materials that help caregivers identify potential developmental delays and disabilities, promoting parent and family involvement in all community activities, and encouraging community efforts supporting inclusion of children with special needs and their families.
Early On Michigan Family Guidebook in Arabic. Early On provides early intervention services for children, ages birth up to age 3, with developmental delay(s) and/or disabilities, and their families.
This is a brief description with an illustrative animation intended to show how burning fossil fuels (using gasoline as an example) yields carbon dioxide that weighs more than the fuel itself.
published in the journal Molecules, 2012-04; This review presents findings that indicate honey may improve oxidative stress in chronic diseases, such as in the gastrointestinal tract (GIT), liver,
pancreas, kidney, reproductive organs and plasma/serum.
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