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Daniel C. Whitehead

Photo of Dan WhiteheadAssistant Professor
Organic Chemistry

Phone: (864) 656-5765
Office: 467 Hunter
E-mail: dwhiteh@clemson.edu

Research Interests | Publications

Dr. Whitehead received his B.S. (2002) and M.S. (2003) degrees in chemistry from Furman University, working in the labs of Professor Larry Trzupek.   He earned his Ph. D. (2009) from Michigan State University under the mentorship of Professor Babak Borhan.  His doctoral research focused on the development of novel asymmetric olefin halogenation reactions culminating in the development of an asymmetric chlorolactonization protocol.  He was a postdoctoral fellow (2009-2011) at North Carolina State University in the labs of Professor Christian Melander.  His postdoctoral studies focused on the development of novel therapeutics including anti-biofilm agents, osteoclastogenesis inhibitors, and nanoparticle-drug conjugates for the treatment of HIV infections.  Dr. Whitehead joined the Clemson University Chemistry Department in 2011.  In 2016, Dr. Whitehead assumed the role of Chemistry Undergraduate Program Coordinator.

Research Interests

The Whitehead group leverages synthetic organic chemistry to explore three focus areas:  1.) new reaction methodology, 2.) materials chemistry, and 3.) bio-organic chemistry.  The Whitehead group is always looking for motivated graduate students and undergraduate researchers.  Please contact Dr. Whitehead by email if you are interested.

New Reaction Methodology

Our group actively explores the development of new reaction methodology, focusing mainly on new oxidation methods.  Early efforts centered on the exploration of oxidations mediated by heterogeneous catalysts comprised of vanadium (V) oxide1-3 and related polyoxovanadates.4,5  Additionally, an NSF-sponsored project (CHE-1664920) is focused on the development of novel peptide-based iodoarene catalysts for the development of enantioselective hypervalent iodine catalysts.6  Other projects that are underway include the investigation of chiral boronate esters as chiral control elements in the Diels-Alder cycloaddition and the exploration of novel cycloaddition chemistry between electron-rich alkynes and azodicarboxylates to generate hitherto rarely accessible heterocycles.

Materials Chemistry

Our efforts in  materials chemistry are focused on two specific areas.  First, in collaborative efforts with bioengineers at Clemson, we have developed a series of biodegradable, functional nanoparticles that are capable of capturing VOC pollutants associated with industrial waste streams.7,8  We are currently studying the application of related functional micro and nanomaterials for the remediation of other important environmental contaminants including organophosphorus pesticides, flame retardants, and chemical warfare agents.

Secondly, in collaboration with Clemson Bioengineers and chemists at the College of Charleston, we are stuying the development of novel biodegradable polymeric materials that are X-ray opaque, and thus compatible with medical imaging techniques like X-ray and CT.9-11  We are currently exploring the development of X-ray imagable, injectable nanoparticles for various biomedical applications.

Bio-organic Chemistry

Bio-organic research efforts in the Whitehead group have focused two separate projects.  First, as a part of a collaborative team of parasitologists and chemists at Clemson, Brigham Young University, and the University of Wisconsin, our group has been investigating a novel drug delivery strategy for the development of potent anti-trypanosomal drugs, for the potential treatment of neglected tropical diseases such as African Sleeping Sickness.12-14 

In a second project, the Whitehead group collaborates with a diverse group of scientists at Clemson, the University of North Carolina at Chapel Hill, and the University of Florida to study the development of small molecule inhibitors of the polysaccharide metabolism  of prominent gastrointestinal microbes resident in the human gut.  The successful development of potent inhibitors of these microbial metabolic processes may have therapeutic potential for a variety of human diseases associated with undesirable changes in the gastrointestinal microbiota.

Outreach

Dr. Whitehead is passionate about scientific outreach.  In 2009, he co-founded a science outreach program to facilitate laboratory exercises for area homeschool students.15  He routinely collaborates with an area Montessori pre-primary and primary school to conduct hands-on science experiments and demonstrations.

 

 

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Whitehead Group Publications (;denotes undergraduate co-author):

1.  Drew, E.T.; Yang, Y.; Russo, J.A.; Campbell, M.L.; Rackley, S.A.; Hudson, J.; Schmuki, P.; Whitehead, D.C. "Evaluation of nanostructured vanadium(V) oxide in catalytic oxidations" Catal. Sci. Technol. 2013, 3, 2610-2613.

               - Selected as a July 2013 "Hot" Article by reviewers and editors of Catal. Sci. & Technol.

2.  Campbell, M. L.; Rackley, S.A.; Giambalvo, L. N.; Whitehead, D. C. "Bromolactonization of Alkenoic Acids Mediated by V2O5 via Bromide to Bromenium in situ Oxidation" Tetrahedron Lett. 2014, 55, 5680.

3.  Campbell, M. L.; Rackley, S. A.; Giambalvo, L. N.; Whitehead, D. C. "Vanadium (V) oxide mediated bromolactonization of alkenoic acids" Tetrahedron, 2015, 71, 3895-3902.

4.  Campbell, M. L.; Sulejmanovic, D.; Schiller, J. B.; Turner, E. M.; Hwu, S. -J.; Whitehead, D. C. "Room-Temperature Catalytic Oxidation of Alcohols with the Polyoxovanadate Salt Cs5(V14As8O42Cl)" Catal. Sci. Technol.2016, 6, 3208-3213.

5.  Campbell, M. L.; Sulejmanovic, D.; Schiller, J. B.†; Turner, E. M. ; Hwu, S.-J.; Whitehead, D. C. "Alcohol oxidations using reduced polyoxovanadates" Helv. Chim. Acta, 2017, 100, e1600338.

6.  Lex, T. R.; Swasy, M. I.; Whitehead, D. C. "Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations" J. Org. Chem. 2015, 80, 12234-12243.

7.  Campbell, M. L.; Guerra, F. D.;  Alexis, F.;  Whitehead, D. C. "Target-Specific Capture of Environmentally Relevant Gaseous Molecules with Functional Nanoparticles", Chem. Eur. J2015, 21, 14834-14842.

8.  Guerra, F. D.; Smith Jr, G. D.; Alexis, F.; Whitehead, D. C. "A survey of VOC emissions from rendering plants" Aerosol Air Qual. Res. 2017, 17,209-217.

9.  Olsen, T. R.; Davis, L. L.; Nicolau, S. E.; Duncan, C. C.; Whitehead, D. C.; Van Horn, B. A.; Alexis, F. "Non-Invasive Deep Tissue Imaging of Polyesters Using XRay" Acta Biomater. 2015, 20,94-103.

10. Nicolau, S. E.†;  Davis, L. L.; Duncan, C. C.; Olsen, T. R.; Alexis, F. Whitehead, D. C.; Van Horn, B. A. "Oxime Graft Strategy for Iodinated Poly(epsilon-caprolactone) Xray Opaque Materials", J. Polym. Sci. A Polym. Chem. 2015, 53, 2421-2430.

11. Van Horn, B. A.; Davis, L. L.†; Nicolau, S. E.†; Burry, E. E.†; Bailey, V. O.†; Guerra, F. D.; Alexis, F.; Whitehead, D. C. "Synthesis and Conjugaton of a Triiodohydroxylamine for the Preparation of Highly X-ray Opaque Poly(epsilon-caprolactone) Materials" J. Polym. Sci. A Polym. Chem. 2017, 55, 787-793.

12. Joice, A. C.; Harris, M. T.; Kahney, E. W.; Dodson, H. C.; Maselli, A. G.; Whitehead, D. C.; Morris, J. C. "Exploring the mode of action of ebselen in Trypanosoma brucei hexokinase inhibition" Int. J. Parasitol. Drug Drug Resist. 2013, 3, 154-160.

          - Selected as "Editor's Choice".

13. Gordhan, H. M.; Patrick, S. L.; Swasy, M. I.; Hackler, A. L.†; Anayee, M. ; Golden, J. E.; Christensen, K. A.; Morris, J. C.; Whitehead, D. C. "Evaluation of substituted ebselen derivatives as potential tyrpanocidal agents" Bioorg. Med. Chem. Lett. 2017, 27, 537-541.

14. Gordhan, H. M.; Milanes, J. E.; Qiu, Y.; Golden, J. E.; Christensen, K. A.; Morris, J. C.; Whitehead, D. C. "A targeted delivery strategy for the development of potent trypanocides" Chem. Commun. 2017, 53, 8735-8738.

15. Hercules, D. A.; Parrish, C. A.; Whitehead, D. C. "Evaluating a college-prep laboratory exercise for teen-aged homeschool students in a university setting" J. Chem. Educ. 2016, 93, 870-873.

 

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