Dr. Stephen Starnes
Texas A&M University-Commerce
Commerce, Texas 75429
Phone: 903-886-5389 Fax: 903-468-6020
Post doc, Molecular Recognition, The Scripps Research Institute,
La Jolla, California, 1998-2000
Ph.D., Organic Chemistry, Texas Tech University,
Lubbock, Texas, 1998
B.S., Chemistry, Texas Tech University, 1993
CHEM 107 - Survey of General Chemistry
CHEM 108 - Survey of Organic and Biochemistry
CHEM 201 - Organic Problem Solving I
CHEM 211 - Organic Chemistry
CHEM 212 - Organic Chemistry
CHEM 513 - Organic Mechanisms and Structure
Chem 1411, 1412- US-General/Quant Chemistry I & II
Chem 515- Organic synthesis
Chem 527- Chemical and Biochemical Characteristic Methods I
Chem 529- Chemistry Workshop
Synthesis and characterization of phthalocyanine compounds designed to self-assemble as discrete dimers. Investigation of their molecular recognition properties.
Synthesis of porphyrin-resorcinarene hybrids for molecular recognition, catalysis and energy transfer applications.
Graduate Research (May 1993-1998)
Asymmetric synthesis of conformationally constrained cysteine analogs.
Analysis of the conformational potential energy surface of unnatural amino acids as a function of their substituents using ab initio computational techniques.
Synthesis of unnatural amino acids and examination of their tautomerism, conformation, and aggregation in solution using spectroscopic techniques.
Awards, Honors & Scholarship
• Paul W. Barrus Distinguished Faculty Award for Teaching, Texas A&M University-Commerce, 2012
• Donald C. Roush Excellence in Teaching Award, New Mexico State University, 2004
• Patricia Christmore Faculty Teaching Award, New Mexico State University, 2003-2004
• Song Prize, award for best dissertation, Texas Tech University, 1998
• Outstanding Doctoral Teaching Assistant Award, Texas Tech, 1996-1997
Undergraduate Honors Thesis
Masters Theses Directed
2. MariJo Wienkers, "Meso Substituted Metallated Porphyrin Based Receptors for Anion Recognition," June 28, 2004.
3. Josmalen Ramos, “Synthesis and Characterization of Face-To-Face Porphyrin in Anion Recognition, ” summer 2009.
4. Lakshmi Koya, “Porphyrin-Proline Hybrids: Hosts for Chiral Guest Recognition,” November 3, 2011.
5. Himajarani Surapaneni, “4-Hydroxy proline-porphyrin hybrids: chiral porphyrins for anion recognition”, November 4, 2011.
6. Prathima Kavuri, “1,2-Diamine and 1,2-Amine Alcohol-Porphyrin Hybrids: Chiral Recognition for Anion Recognition,” March 30, 2012.
7. Lin Chen, “Chiral Nitrogen Heterocyclic Porphyrin Compounds for Chiral Recognition,” August 2012.
8. Karthik Akinapelli, “Synthesis of Chiral Porphyrins and Structural Studies of their Host:Guest Complexes,” September 14, 2012.
9. Vijay Nandipati, “3-Aminopyrrolidine-Porphyrin Receptors: Chiral Porphyrins for Anion Recognition,” Masters candidate, defended October 19, 2012.
10. Anusha Bomiddi, “Synthesis and Study of Enhanced Shape Selective Anion Hosts,” Masters candidate, defended October 24, 2012.
11. MingHsun Yang, “Proline Sulfonamide-Porphyrin Derivatives: 19F-NMR and UV Detection of Chiral Recognition for Anions and Amines,” Masters candidate, defended November 1, 2012.
Awards Received by my Research Students
2.Joey Ramos, graduate 1st place overall winner in the Masters student division at the 2008 Pathways symposium.
3.Jeffery Sun, Discipline winner, undergraduate, 2nd place in the physical sciences at the 2010 Pathways symposium.
4.Jeffery Sun selected to present a poster over his research in Austin, February 14, 2011 at the Undergraduate Research Day at the Capitol: Transforming Texas Through Undergraduate Research.
5.Xiaowen Wu, Best graduate presentation in the College of Science, Agriculture and Engineering, 2012 Annual Research Symposium, Texas A&M-University Commerce.
6.Karthik Akinapelli, 3rd place in graduate presentation in the North Texas Life Science Research Symposium, UNT Health Science Center, Fort Worth, TX, Nov. 3, 2012.
Anion and molecular recognition
Design and synthesis of porphyrin based receptors
Design and synthesis of sensors for anions of biomedical and environmental relevance
Research is a necessary component for the training of any student in chemistry (or science in general). Research helps a student understand the content and relevance of lecture material, it provides them the necessary skills to succeed in a scientific career and it is one of the most effective means of engaging and retaining a student in a STEM field. Training students in the art of research should start as early as possible (their freshman year or even while in high school). I have had high school students conduct research in my labs as part of the ACS-SEED program. Each semester, there are typically 4-5 undergraduate students (freshman year and beyond) and 4-5 Masters thesis students under my research guidance. Chemistry majors can count 6 credits of research (Chem 418 or 497) towards their degree.
My research is primarily in the area of molecular recognition. The majority of the work centers on the utilization of porphyrins to develop synthetic hosts for chiral and non-chiral anionic and neutral guests. We also are working to better understand the nature of the halogen-bonding interaction. Our work is fundamental in nature aimed at understanding basic molecular and molecule-ion interactions. Most recently, much of our research efforts are aimed at developing chiral porphyrins. Although we utilize these compounds to study molecular recognition phenomena, the ultimate goal of these research efforts are diverse; the results of this research should aid in developing more selective catalysts for chiral and non-chiral reactions (since molecular recognition is at the heart of many catalytic reactions), developing new materials (many modern materials are constructed through self-assembly interactions which is a molecular recognition event). The work also contributes to a better understanding of biological interactions, much of which are molecular recognition events. The research in my group is multidisciplinary. Students in the group gain skills in synthetic organic chemistry, analytical chemistry, and computational chemistry.
Research students in my group are trained in moderately complex synthetic organic chemistry techniques and the use of instrumentation (NMR (1H-NMR, 13C-NMR including DEPT, 19F-NMR, 2D-NMR such as COSYand HETCOR), UV/Vis, fluorescence, and circular dichroism spectroscopy, HD-Mass Spectrometry and polarimetry) and computational chemistry (Spartan and Gaussian software packages on a Beowulf cluster). All research students in the group will be trained to use these instruments and will be expected to conduct their own experiments on the instruments.
Students in the group have ample opportunity to present their research. Each year the chemistry department provides for students to present at the regional meeting of the ACS, the annual Texas A&M System Pathways Symposium, the TAMU-C annual research symposium and the local ACS Meeting in Miniature symposium. We also aim to attend national meetings of the ACS as well as international conferences such as the International Conference on Porphyrins and Phthalocyanines, the International Symposium on Macrocyclic and Supramolecular Chemistry and the International Symposium on Chirality.
Biomedical applications of my research—A major research goal of my group is the development of synthetic receptors for anions such as phosphate derivatives (nucleotides, DNA, RNA for example), carboxylates, halides (chloride, fluoride), and amino acids (through carboxylate recognition). The development of receptors for these analytes has diagnostic applications in the monitoring of cellular processes. The group is also focused on the design of receptors that serve as carriers for the membrane transport of anions such as nucleotides and chloride. Receptors that function in this way could find therapeutic applications in the treatment of cystic fibrosis (a disease characterized by defective chloride channel proteins) and viral diseases (via the membrane transport of nucleotide antiviral agents). In general, we aim to contribute to a better understanding of biological molecular recognition events through the study of our synthetic systems.
Environmental applications—There are several anionic species of environmental concern such as radioactive pertechnetate, which is a by-product of the nuclear fuel cycle, and nitrate, which is present in large quantities in radioactive tank wastes and has been implicated in high incidences of lymphoma when present in large quantities in groundwater. My group is interested in the development of receptors that can detect the presence of these species and that can serve as extraction and transport agents for the removal of these and other anionic environmental contaminants.
Synthesis applications—Numerous reagents utilized in organic synthesis are anionic in nature. Additionally, and perhaps more importantly, numerous reactions proceed through anionic transition states. Receptors for anionic reagents, intermediates, and transition states could be used to direct the course of or catalyze reactions involving these species. My group is developing receptors that serve as supramolecular chiral auxiliaries and catalysts for asymmetric synthetic transformations such as Aldol and Michael type reactions.
- Wu, Xiaowen; Starnes, Stephen D. "L-Nipecotic Acid-Porphyrin Derivative: A Chiral Host with Introverted Functionality for Chiral Recognition," Org. Letters, 2012, 14, 14, 3652-3655.
- MariJo Wienkers, Josmalen Ramos, Hikma Jemal, Chaz Cardenas, Paul Wiget, Alfreda Nelson, Shiloh Free, Jun Wu, Rebecca Roach, Marius Vulcan, Kristopher Waynant, Kyle Fort, Anna Vladimirova, Jeffery Sun, Samuel Eli Hunt, Dmitry M. Rudkevich, Stephen D. Starnes “Enhanced Shape-Selective Recognition of Anion Guests through Complexation- Induced Organization of Porphyrin Hosts,” Org. Letters, 2012, 14, 6, 1370-1373.
- Whaley, W. L.; Rummel, J. D.; Zemenu, E.; Li, W.; Yang, P.; Rodgers, B. C.; Bailey, J.; Moody, C. L.; Huhman, D. V.; Maier, C. G.-A.; Sumner, L. W.; Starnes, S. D.. Isolation and characterization of osajin and pomiferin: Discovery laboratory exercises for organic chemistry. Chemical Educator, 2007, 12(3), 179-184.
Starnes, S.D.;Birney, D. M. "Parallel Combinatorial Esterification: An Experiment for the Second Semester Organic Chemistry Laboratory", accepted, Chemical Education Resources: Modular Laboratory Program in Chemistry.
Starnes, S. D.; Arungundram, S.; Saunders, C. H. "Anion Sensors Basedon b,b'-Disubstituted Porphyrin Derivatives,"Tetrahedron Letters, 2002, 43,7785.
Headley, A. D.; Starnes, S. D., "Conformational analysis of a-trifluoroalanine: a theoretical study," J. Mol. Struct. (THEOCHEM), 2001,572, 1-3, 89-95.
Starnes, S. D.; Rudkevich, D. M.; Rebek, J. Jr. "Cavitand-Porphyrins," J. Am. Chem. Soc. 2001, 123, 4659-4669.
Starnes, S.D.; Rudkevich, D.M.; Rebek, J., Jr. "A Cavitand-Porphyrin Hybrid," Org. Lett., 2000, 2, 1995-1998.
Headley, A.D.; Starnes, S.D. "Ab Initio Study of Anomeric Effect In 2,2-Difluoroglycine," J. Mol. Struct. (THEOCHEM), 2000, 507, 281-287.
Lutzen, A.; Starnes, S.D.; Rudkevich, D.M.; Rebek, J., Jr. "A Self-Assembled Phthalocyanine Dimer," Tetrahedron Lett., 2000, 41, 20,3777-3780.
Headley, A.D.; Starnes, S.D., "Theoretical Analysis of Fluoroglycine Conformers," J. Comput. Chem., 2000, 21, 6, 426-431.
Birney, D.M.; Starnes, S.D., "Parallel Combinatorial Esterification; A Simple Experiment for Use in the Second Semester Organic Chemistry Laboratory," J. Chem. Ed., 1999, 76, 11, 1560-1561.
Headley, A.D.; Starnes, S.D. "Association of p-Toluyldimethylglycine in Water," J. Phys. Org. Chem. 1999, 12, 290-292.
Headley, A.D.; Starnes, S.D., "Theoretical Studies of the Gas Phase Tautomerization of Sarcosine," J. Mol. Struct. (THEOCHEM), 1999, 467, 2, 95-101.