Rwanda Day 2011, Chicago
Elbert L. Fausett Distinguished Professor of Chemistry
- Robert A. Welch Foundation Postdoctoral Fellow, Rice University
- Ph.D., University of Arkansas
- B.S., Ouachita Baptist University
Prospecting for Pheremones Via Green Solventless Extraction Techniques
African Elephant (Loxodonta africana)
Collaboration with Dr. Bruce Schulte, Western Kentucky University
Ring-Tailed Lemur (Lemur catta)
Collaboration with Dr. Christine Drea, Duke University
Maned Wolf (Chrysocyon brachyurus)
Collaboration with Dr. Nucharin Songasen, Smithsonian's Conservation Research Center, and Little Rock Zoo
Milne-Edwards Sifaka (Propithecus edwardsi)
Collaboration with Dr. Pat Wright, Stony Brook University, Dr. Toni Lyn Morelli, University of California-Berkeley, and Dr. Andrew Hayes, Agri-Science Queensland, Brisbane, Australia
Binturong (Arctictis binturong)
Collaboration with Dr. Christine Drea, Duke University
Kakapo (Strigops habroptilus)
Collaboration with Dr. Dianne Brunton and Anna Gsell, Massey University, Auckland, NZ, & Dr. Dave Greenwood, University of Auckland
Polar Bear (Ursusmaritimus)
Collaboration with Dr. Megan Owen, San Diego Zoo
Bornean Orang-utan (Pongo pygmaeus)
Collaboration with Melanie Bond, Center for Great Apes, Wauchula, FL , and Dr. Graham L. Banes, Max Planck Institute for Evolutionary Anthropology, Leipzig, Germany; CAS-MPG Partner Institute for Computational Biology, Shanghai, PRC; School of Veterinary
Medicine, University of Wisconsin-Madison; Henry Vilas Zoo, Madison, WI 53715
"Our understanding of mammalian pheromones is limited, owing to the complexity of mammalian life and the mammalian brain. Mammals integrate information received by their various senses, and this enormously complicates efforts to understand any specific
signal. In addition, interpreting the reaction to a signal can be difficult. The reactions of mammals are not automatic, and their behavior is not necessarily reproducible. Sometimes a pheromone produces no obvious response in a mammal. Perhaps the animal
has ignored the signal, or perhaps it has learned something for future use. In general, behavioral studies on mammalian pheromones are much more extensive than chemical research." ---William C. Agosta. 1994 Using Chemicals to Communicate. Journal of Chemical Education.
Adventures with Undergraduates and Other Mammals
I am a synthetic
organic chemist who often masquerades as a chemical ecologist. The synthetic
organic chemistry brain cells are focused these days largely on three projects:
(1) the development of green chemistry experiments for the
introductory organic chemistry lab. We are particularly interested in
solventless reactions and reactions in or on water; (2) the enantioselective preparation of metabolites of the
anti-coagulation drug, warfarin (Coumadin) to be used as standards in LC-MS as
part of a study of human warfarin metabolism by Professor Grover Paul Miller in the Department of
Biochemistry and Molecular Biology at the University of Arkansas for Medical
Sciences; (3) using the Suzuki reaction of bromine-substituted isatins with
various boronic acids, followed by N-acetylation
and ring opening with methyl esters of amino acids or small peptides to provide
glyoxylamide peptidomimetics to be tested as potential antibacterials. This is in collaboration with Professors
David Black and Naresh Kumar of the School of Chemistry, University of New
South Wales (Australia).
ecology brain cells are involved primarily with a study of chemical
communication, primarily among mammals.
These studies include the following animals (Biology collaborators): elephants (collaboration with Bruce
Schulte, Western Kentucky University); lemurs
(several types) (a. Christine Drea, Duke University; b. Toni Lyn
Morelli/Patricia Wright, SUNY-Stony Brook; Andrew Hayes, Department of
Agriculture, Fisheries and Forestry, Horticulture and Forestry Science,
Agri-Science Queensland, Brisbane, Queensland, Australia ); maned wolves (Nucharin Songsasen,
Center for Species Survival, Smithsonian Conservation Biology Institute); kakapo (Anna Gsell/Diane Brunton,
Massey University, Auckland, New Zealand); Dave Greenwood (Auckland University);
polar bears (Megan Owen, San Diego
Zoo); orang-utans; Melanie Bond (Center for Great
Apes, Wauchula, FL) and Graham L. Banes (Max Planck Institute for Evolutionary
Anthropology, Leipzig, Germany; CAS-MPG Partner Institute for
Computational Biology, Shanghai, PRC; School of Veterinary Medicine, University
of Wisconsin-Madison, WI; Henry Vilas Zoo, Madison, WI. Our chemical ecology analyses involve a solventless extraction technique
(solid phase dynamic extraction; SPDE) in conjunction with GC-MS.
Please see the list
of publications below, in which more information about our research can be
found. Regardless of the exact nature or goal of our research, a primary
objective is undergraduate education: teaching science by doing science. To
date, over 130 undergraduate collaborators have worked on our various research
projects full time in the summer and/or part time during the academic year.
Virtually all of these students have presented the results of their research
during at least one national scientific meeting and many have been co-authors
on a peer-reviewed scientific paper.
Summer Research Group 2010
Summer Research Group 2011
Summer Research Group 2012
Honors, Professional Societies, and Responsibilities
- Co-Chair of the 2014 Chemical Signals in Vertebrates conference in a joint meeting with the International Society of Chemical Ecology at the University of Illinois, July 2014.
- Organized and spoke at symposium entitled “Searching for Chemical Signals in Vertebrates: Extractions from Biological Media as a Prelude to GC-MS Analysis”; Chemical Signals in Vertebrates conference, Berlin, Germany, August, 2011.
- Attended CUR workshop “Gateways to Best Practices for Undergraduate Program Directors, June, 2011, Washington University.2010 Council on Undergraduate Research CUR Fellow Award
- 2008 Invited Speaker, Stanford University, William S. Johnson Symposium in Organic Chemistry
- 2007 Recipient Pfizer-St. Louis Green Chemistry Research and Education Grant
- One of six keynote speakers at Research Corporation workshop for chemistry and physics faculty, and administrators in Tucson. “Models of Academic Leadership”; August, 2004.
- 2003 U.S. Professor of the Year (for baccalaureate colleges), awarded by the Carnegie Foundation for the Advancement of Teaching, and the Council for Advancement and Support of Education (CASE)
- Recipient of the Faculty Appreciation Award by the Hendrix College Class of 2002 and the Class of 2003 for "excellence in instruction and concern for students’ welfare"
- Visiting Fellow, Research School of Chemistry, Australian National University, Canberra (with Professor Martin Banwell), June, 2000
- Awarded 1998 David W. Mellor Medal for Chemical Education by the University of New South Wales, Sydney, Australia, and delivered the Mellor Address
- 1993 Chair, Gordon Research Conference on Heterocyclic Compounds
- American Chemical Society
- Phi Beta Kappa
- Council on Undergraduate Research (CUR) (President, 1992-93)
- Founding Co-Editor, CUR Quarterly, 1993-1996
- Recipient, Camille and Henry Dreyfus Foundation Scholar/Fellow Program for Undergraduate Institutions (1989)
- Board Member, Riddle's Elephant Sanctuary
- Signal Officers Basic Training, U.S. Army, Fort Gordon, Georgia, 3 months, fall 1973 (4 years of Army ROTC, Ouachita Baptist University, 1965-1969; Honorable Discharge from U.S. Army Reserves as a Captain, 1977).
Grants and Proposals
- Tom Goodwin (PI); Co-PIs: Chris Marvin, & Andres Caro: “Acquisition of a 400 MHz NMR Spectrometer to Enhance Faculty and Undergraduate Research at Hendrix College,” NSF-MRI, $258,790, 2010.
- Tom Goodwin: National Science Foundation Collaborative Research at Undergraduate Institutions (NSF C-RUI); with Bruce Schulte (Georgia Southern University) and Bets Rasmussen (Oregon Graduate Institute): “Development and Identity of Sexually Dimorphic
Signals and Responses by African Elephants,” 842,251, 2002-2006.
- Morelli, T. L., Hayes, R. A., Nahrung, H. F., Goodwin, T. E., Harelimana, I. H., Macdonald, L. J., & Wright, P. C. 2013. Relatedness communicated in lemur scent. Naturwissenschaften
- delBarco-Trillo, J., Harelimana, I. H., Goodwin, T. E., & Drea, C. M. 2013. Chemical differences between voided and bladder urine in the aye-aye (Daubentonia madagascariensis): Implications for olfactory communication studies. Am. J. Primatol. 75:695-702.
- Drea, C. M., Boulet, M., DelBarco-Trillo, J., Greene, L. K., Sacha, C. R., Goodwin, T. E., & Dubay, G. R. 2013. The ‘secret’ in secretions: Methodological considerations in deciphering primate olfactory communication. Am. J. Primatol. 75:621-642.
- “Hemiterpenoids and Pyrazines in the Odoriferous Urine of the Maned Wolf (Chrysocyon brachyurus,” T. E. Goodwin, N. Songsasen, L. J. Broederdorf, B. A. Burkert, C. J. Chen, S.R. Jackson, B. Keplinger, M. E. Rountree, Z. J. Waldrip, M. E. Weddell,
L. P. Desrochers, W. K. Baker Jr and J. P. F. G. Helsper, Chapter 13 in Chemical
Signals in Vertebrates 12, 2013 M. I. East and M. Dehnhard, Eds., Springer Press, NY, pp 171-184.
- Goodwin, T.E., Broederdorf, L.J., Burkert, B.A., Hirwa, H.H., Mark, D.B., Waldrip, Z.J., Kopper, R.A., Sutherland, M.V. , Freeman, E.W., Hollister-Smith, J.A., and Schulte, B.A. 2012. Chemical signals of elephant musth: Temporal aspects of microbially-mediated
modifications. J. Chem. Ecol. 38:81-87.
- Goodwin, T.E. 2012. The Art of Organic Synthesis: Green Chemists Find a Better Way, in Chemistry for Changing Times. J. W. Hill, T. W. McCreary, D. K. Kolb. 13th edition. New York: Pearson, p. 254.
- Delbarco-Trillo, J., Burkert, B. A., Goodwin, B. A., & Drea, C. M. 2011. Night and day: the comparative study of strepsirrhine primates reveals socioecological and phylogenetic patterns in olfactory signals. J. Evol. Biol. 24:82-98.
- Merte, C.E., Goodwin, T.E., & Schulte, B.A. 2010. Male and female developmental differences in chemosensory investigations by African elephants (Loxodonta africana) approaching waterholes. Behav. Ecol. Sociobiol. 64:401-408.
- Broederdorf, L.J., Meyer, J.M., Freeman, E.W., Goodwin, T.E., & Schulte, B.A. 2009. The elephants of Addo: An undergraduate research adventure. J. Eleph. Managers Assoc. 20:27-31.
- Meyer, J.M., Freeman, E.W., Goodwin, T.E., & Schulte, B.A. 2009. Monitoring African elephant chemical communication and hormone activity in Addo Elephant National Park, South Africa. J. Eleph. Managers Assoc. 20:32-36.
- Goodwin, T.E. The Garden of Green Organic Chemistry at Hendrix College. In Changing the Course of Chemistry:
Green Chemistry Education; Anastas, P.T., Levy, I.J., Parent, K.E., Eds.; ACS Symposium Series 1011; American Chemical Society: Washington, DC, 2009; pp 37-53.
- Goodwin, T.E. & Schulte, B.A. 2009. Prospecting for mammalian chemical signals via solventless extraction techniques: an elephantine task. ChemoSense, 11(2), 9-15.
- McKenzie, L.C.; Huffman, L.M.; Hutchison, J.E.; Rogers, C.E.; Goodwin, T.E.; and Spessard, G.O. 2009.
Greener Solutions for the Organic Chemistry Teaching Lab: Exploring the Advantages of Alternative Reaction Media. J. Chem. Educ., 86,
- Loizi, H., Goodwin, T.E., Rasmussen, L.E.L., Whitehouse, A.M. & Schulte, B.A. 2009. Sexual dimorphism in the performance of chemosensory investigatory behaviours by African elephants (Loxodonta
africana). Behaviour, 146, 373-392.
- "Intrasexual chemical communication and social responses of captive female African elephants, Loxodonta
africana" Meyer, J.M.; Goodwin, T.E.; Schulte, B.A. Animal Behavior
2008, 76, 163-174.
- Castelda, S.M., Goodwin, T.E. & Schulte, B.A. 2008. Investigating chemical signals in African elephants for convergence with insects and similarities with Asian elephants. Pp. 81-91, in: Proceedings of the 2007 International Elephant
Conservation & Research Symposium, Orlando, FL.
- "Use of Automated Solid Phase Dynamic Extraction (SPDE)/GC-MS and Novel Macros in the Search for African Elephant Pheromones," T. E. Goodwin, P. A. Brown, M. S. Eggert, M. G. Evola, S. J. House, R. G. Morshedi, M. E. Weddell, C. J. Chen, S. R. Jackson,
Y. Aubut, J. Eggert, B. A. Schulte, L. E. L. Rasmussen, Chemical Signals in
Vertebrates 11 2007 J. Hurst, R. Beynon, T. Wyatt, & C. Roberts, Eds., Springer Press, NY, pp 25-35.
- "Honest Signalling through Chemicals by Elephants with Applications for Care and Conservation", Schulte, B. A.; Freeman, E. W.; Goodwin, T. E.; Hollister-Smith, J.; Rasmussen, L.E.L. Applied Animal Behaviour Science 2007, 102, 344-363.
- "Insect Pheromones and Precursors in Female African Elephant Urine", Goodwin, T. E.; Eggert, M. S.; House, S. J.; Weddell, M. E.; Schulte, B. A.; Rasmussen, L. E. L., Journal
of Chemical Ecology 2006, 32, 1849-1853.
- "Palladium-catalysed Cross-coupling and Related Reactions Involving Pyrroles" Banwell, M. G.; Goodwin, T. E.; Ng, S.; Smith, J. A.; Wong, D. J. European Journal of
Organic Chemistry 2006, 14, 3043-3060.
- "Male African elephants (Loxodonta
africana) can distinguish oestrous status via urinary signals", Bagley, K. R.; Goodwin, T. E.; Rasmussen, L. E. L.; Schulte, B. A. Animal
Behaviour 2006, 71, 1439-1445.
- "African Elephant Chemical Communication and Humans in Tanzania", Schulte, B. A.; Napora, E.; Vyas, D.K.; Goodwin, T. E.; Rasmussen, L. E. L. J. Elephant Managers Association 2006,
- "African elephant births and post-partum events in West Kilimanjaro, Tanzania", Vyas, D. K.; Goodwin, T. E.; Rasmussen, L.E.L.; Schulte, B. A. J. Elephant Managers Association 2006,
- "Elephant Death Possibly by Constipation", Vyas, D. K.; Goodwin, T. E.; Rasmussen, L.E.L.; Schulte, B. A. Pachyderm 2005, 39, 93-96.
- "Chemical Analysis of Preovulatory Female African Elephant Urine: A Search for Putative Pheromones", Goodwin, T. E.; Rasmussen, L. E.L.; Schulte, B. A.; Brown, P. A.; Davis, B. L.; Dill, W. M.; Dowdy, N. C.; Hicks, A. R.; Morshedi, R. G.; Mwanza, D.;
Loizi, H., Chemical Signals in Vertebrates 10 2005, R. T. Mason, M. P. LeMaster, and D. Muller-Schwarze, eds., Springer, NY, pp 128-139.
- "Hormone Receptor Expression in Interdigital Glands of the Asian Elephant (Elephas maximus)", Lamps, L. W.; Smoller, B. R.; Goodwin, T. E.; Rasmussen, L. E. L., Zoo
Biology 2004, 23, 463-469.
- "An Asymptotic Approach to the Development of a Green Organic Chemistry Laboratory", Goodwin, T. E., J.
Chem. Educ. 2004, 81, 1187-1190.
- "Elephant Chemotactile Communication and Conservation", Schulte, B. A.; Loizi, H.; Bagley, K.; Gray, A.; Stanley, L.; Correll, M.; Goodwin, T. E.; Brown, P. A.; Davis, B. L.; Dill, W. M.; Dowdy, N. C.; Hicks, A. R.; Morshedi, R. G.; Mwanza, D.; Rasmussen,
L. E. L. J. Elephant Managers Assoc. 2004, 15, 16-23.
- "African Elephant Sesquiterpenes. II. Identification and Synthesis of New Derivatives of 2,3-Dihydrofarnesol", Goodwin, T. E.; Brown, F. D.; Counts, R. W.; Dowdy, N. C.; Fraley, P. L.; Hughes, R. A.; Liu, D. Z.; Mashburn, C. D.; Rankin, J. D.; Roberson,
R. S.; Wooley, K. D.; Rasmussen, E. L.; Riddle, S. W.; Riddle, H. S.; Schulz, S. J. Nat. Prod. 2002, 65, 1319-1322.
- "Initial Studies on the Source and Cyclic Release Pattern of (Z)-7-Dodecenyl Acetate, the Preovulatory Pheromone of Female Asian Elephants," L. E. L. Rasmussen and T. E. Goodwin, Chem. Senses 2000, 25, 603.
- "Characterization of Interdigital Glands in the Asian Elephant (Elephas maximus)", L. W. Lamps, B. R. Smoller, L.E.L. Rasmussen, B. E. Slade, G. Fritsch, and T. E. Goodwin Research in Veterinary Science 2001, 71, 197-200.
- "Unwinding of Unnatural Substrates by a DNA Helicase", A. J. Tackett, P. D. Morris, R. Dennis, T. E. Goodwin, K. D. Raney, Biochemistry 2001, 40, 543-548.
- "Enhanced Pneumocystis
carinii Activity of New Primaquine Analogs", T. E. Goodwin, C. J. Boylan, W. L. Current, J. C. Byrd, C. B. Edwards, D. A. Fuller, J. L. Green, C. D. Larocca, K. D. Raney, A. S. Ross, and W. A. Tucker, Bioorg. Med. Chem.
Letters 2000, 10, 2205-2208.
- "The First Disclosure and Preliminary Investigation of a Liquid Released from the Ears of African Elephants", H. S. Riddle, S. W. Riddle, L. E. L. Rasmussen, and T. E. Goodwin, Zoo Biology 2000, 19, 475-480.
- "Synthesis of
13C,2H3-Salmeterol: An Analytical Internal Standard for Pharmacokinetic Studies," T. E. Goodwin, X. Zhou, P. A. Haile, P. Breen, P. J. Anderson, F. C. Hiller, and C. M. Compadre Journal of Labelled Compounds and
Radiopharmaceuticals, 2000, 43, 65-75.
- "African Elephant Sesquiterpenes," T. E. Goodwin, L. E. L. Rasmussen, A. C. Guinn, S. S. McKelvey, R. Gunawardena, S. W. Riddle, and H. S. Riddle Journal of Natural
Products, 1999, 62, 1570-1572.
- "A Multistep Synthesis of 4-Nitro-1-Ethynylbenzene Involving Palladium-Catalyzed Carbon-Carbon Bond Formation, Conformational Analysis Using NMR Spectroscopy and Molecular Modeling, Acetal Hydrolysis, and Oxidative Decarbonylation," T. E. Goodwin, E.
M. Hurst, and A. S. Ross J. Chem. Educ.1999, 76, 74-75.
- "Observations on the Stereochemistry of Reduction of 2,6-Dimethylcyclohexanones," T. E. Goodwin, J. M. Meacham, M. E. Smith Canadian J. Chem.1998, 76, 1308-1311.
- "A Simple Procedure for Solid Phase Synthesis of Peptide Nucleic Acids with N-Terminal Cysteine," T. E. Goodwin, R. D. Holland, J. O. Lay, Jr., and K. D. Raney Bioorg. Med. Chem. Lett.1998,
- "Synthesis of Conformationally Mobile Bicyclic Tetrahydro-1,2-Oxazines by Isomerization of Isoxazolidinylmethyl Tosylates," T. E. Goodwin, D. M. Cousins, S. D. Debenham, J. L. Green, M. L. Guyer, E. G. Jacobs, T. R. Hoye, D. O. Koltun, and J. R. Vyvyan J. Org. Chem. 1998, 63,
- "Synthesis of Highly Phenylated Poly(p-phenylene vinylenes) via a Chlorine Precursor Route," B. R. Hsieh, W. C. Wan, Y. Yu, Y. Gao, T. E. Goodwin, S. A. Gonzalez, and W. A. Feld Macromolecules
1998, 31, 631-636.
- "Synthesis of Two New Maytansinoid Model Compounds from Carbohydrate Precursors," T. E. Goodwin, K. R. Cousins, H. M. Crane, P. O. Eason, T. E. Freyaldenhoven, C. C. Harmon, B. K. King, C. D. Larocca, R. L. Lile, S. G. Orlicek, R. W. Pelton, O. L. Shedd,
J. S. Swanson, and J. W. Thompson J. Carbohydr. Chem.1998, 17, 323-339.
- "Crystal Structure of (4α,4aα,8aα)-(+)-Octahydro-2-(phenylmethyl)--2H-1,2-benzoxazin-4-ol, 4-Methylbenzenesulfonate (ester)," W. Cordes, J. L. Smith, M. C. Noble, T. E. Goodwin, D. M. Cousins, and E. G. Jacobs J. Chem. Cryst.1998, 28,
- "How to Get Started in Research," a booklet published by the Council on Undergraduate Research, 1995 (Co-authored and edited with B. Holmes, UNC-Asheville) [2nd Edition, 1999].
- "Notes from a Fledgling Elephant Researcher," T. E. Goodwin Journal of the Elephant Manager’s
Association 1997, 8, 42.
- Synthesis of Highly Phenylated Poly(p-phenylenevinylenes) via Halogen Precursor Route (HPR)," S. A. Gonzalez, T. E. Goodwin, W. A. Feld, and B. R. Hsieh Polymer Preprints 1997, 38, April Issue.
- "Stereoselectivity Reversals in Conjugate Additions to a 2,3-Dihydro-4H-pyran-4-one," T. E. Goodwin, N. M. Rothman, K. L. Salazar, S. L. Sorrels, and F. E. Evans J. Org. Chem.1992,
- "Preparation of an Aromatic Synthon for Maytansinoid Synthesis," T. E. Goodwin, S. G. Orlicek, N. R. Adams, L. A. Covey-Morrison, J. S. Jenkins, and G. L. Templeton J.
Org. Chem.1985, 50, 5889-5892.
- "Stereoselective addition of organocopper reagents to a novel carbohydrate-derived 2,3-dihydro-4H-pyran-4-one," T. E. Goodwin, C. M. Crowder, R. B.White, J. S. Swanson, F. E. Evans, and W. L. Meyer J. Org. Chem.1983, 48, 376-380.
- "Synthesis of (E)-1-aryl-2-methyl-3-alkyl-2-propen-1-ones via sulfoxide sulfenate ester rearrangements," T. E. Goodwin, D. G. Ratcliff, C. M. Crowder, and N. K. Seitzinger J. Org. Chem.1982, 47, 815-820.