Steven M. Graham

CHE 1310 Honors General Chemistry I: Introduction to Physical Chemistry
CHE 1321L Honors General Chemistry Lab II: Introduction to Chemical Instrumentation

CHE 1120 Introduction to General and Organic Chemistry II
CHE 1130 Introduction to General and Organic Chemistry III
CHE 1122R Introduction to General and Organic Chemistry II Recitation
CHE 1132R Introduction to General and Organic Chemistry III Recitation

CHE 2230 Organic Chemistry I
CHE 2240 Organic Chemistry II
CHE 2241L Laboratory for Organic Chemistry II

CHE 3260 Advanced Undergraduate Organic Chemistry

CHE 224 Organic Mechanisms Graduate
CHE 227 Organic Spectroscopy Graduate

What do biology, engineering, and architecture have in common? Central to each field is the idea that structure determines function. What a molecule, device, or building can accomplish (function) is determined by how it is put together (structure). In chemistry, structure is more than just knowing which atoms are connected to which other atoms; molecules are inherently “floppy” can assume variety arrangements, or conformations.

Conformational Analysis of Nucleosides, Nucleotides, and cADPR:
Calcium ions (Ca2+) play a major role in regulating diverse biological processes. Much of our work is directed to the synthesis and conformational analysis of the calcium-release agent cyclic adenosine diphosphoribose, or cADPR, as well as the canonical nucleosides and nucleotides found in DNA and RNA. We use a combination of synthesis, NMR spectroscopy, and computational chemistry (ab initio and molecular mechanics) to elucidate the solution structures.
 

Prof. Graham's research page

"Variable-Temperature NMR Spectroscopy, Conformational Analysis, and Thermodynamic Parameters of cADPR Agonists and Antagonists", J. Org. Chem., 2018, 83 (5), 2554–2569.  Saatori, S.-M.; Perez, T.J.; Graham, S.M.

"A variable temperature 600 MHz NMR study of cADPR: structure, conformational analysis, and thermodynamics of the conformational equilibria", Carbohydrate Research, 2018, 455, 71-80.  Javornik, U.; Plazec, J.; Wang, B.; Graham, S.M.

Saatori, S.-M.; Perez, T.J.; Graham, S.M."Variable-Temperature NMR Spectroscopy, Conformational Analysis, and Thermodynamic Parameters of cADPR Agonists and Antagonists," J. Org. Chem., 2018, 83 (5), 2554–2569. 

Javornik, U.; Plazec, J.; Wang, B.; Graham, S.M. "A variable temperature 600 MHz NMR study of cADPR: structure, conformational analysis, and thermodynamics of the conformational equilibria," Carbohydrate Research, 2018, 455, 71-80.  

Hu, B.; Amin, R.; Kumar, S.; Kunaparaju, N.; Graham, S. M.; Barletta, M. A.; William, Z. S. Bioassay-Guided Isolation of the Antidiabetic Active Principle from Salvia Miltiorrhiza and Its Stimulatory Effects on Glucose Uptake Using 3T3-L1 Adipocytes. Med. Chem. Los Angel. CA U. S. 2014, 4, 592–597, 6 pp.

Patel, Pallav D.; Patel, Maulik R.; Kocsis, Bela; Kocsis, Erika; Graham, Steven M.; Warren, Andrew R.; Nicholson, Stacia M.; Billack, Blase; Fronczek, Frank R.; Talele, Tanaji T. “Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles.” European Journal of Medicinal Chemistry. 2010, 45(6), 2214-2222. 

Graham, S.M., Macaya, D.M., Sengupta, R.N., Turner, K.B. “cADPR Analogs: Effect of an Adenosine 2’- or 3’-Methoxy Group on Conformation”. Org. Letters. 2004, 6, 233-236. 

Graham, S.M., Pope, S.C. "The NMR Solution Structure of the Calcium Release Agent Cyclic Adenosine 5’-Diphosphate Ribose (cADPR)”. Nucleosides, Nucleotides, and Nucleic Acids. 2001, 20, 169-183. 

Graham, S.M., Pope, S.C. "Selective Phosphitylation of the Primary Hydroxyl Group in Unprotected Carbohydrates and Nucleosides". Org. Letters. 1999, 1, 733-736. 

Graham, S.M., Ohrtman, L.M. "Boron-Containing Nucleosides. 1. Synthesis of Novel Heterocycle 2-Benzyl-1,4-dihydro-1-hydroxythieno[3,2-c]-[1,5,2]diazaborin-3(2 H)-one: A Thieno-fused 4-Borauracil". J. Het. Chem. 1998, 35, 887 

Graham, S.M.; Prestwich, G.D. "Synthesis and Inhibitory Properties of a Series of Pheromone Substrate Analogues for the Epoxide Hydrase of the Gypsy Moth, Lymantria dispar". J. Org. Chem. 1994, 59, 2956-2966. 

Graham, S. M.; Prestwich, G.D. "Tissue Distribution and Substrate Specificity of an Epoxide Hydrase in the Gypsy Moth, Lymantria dispar". Experientia. 1992, 48, 19-21. 

Graham, S. M.; Prestwich, G.D. Condensation and commentary of A.M. MacMillan and G.L. Verdine, "Synthesis of Functionally Tethered Oligodeoxynucleotides by the Convertible Nucleoside Approach". Chemtracts: Organic Chemistry. 1991, 4, 316-319.  

Prestwich, G.D.; Graham, S. McG.; König, W. "Enantioselective Opening of (+)‑ and (‑)‑Disparlure by Epoxide Hydrase in Gypsy Moth Antennae". J. Chem. Soc., Chem. Comm. 1989, 575‑577. 

Prestwich, G.D.; Graham, S. McG.; Kuo, J.‑W.; Vogt, R.G. "Tritium‑labeled Enantiomers of Disparlure: Synthesis and in vitro Metabolism". J. Am. Chem. Soc. 1989, 111, 636‑642. 

Prestwich, G.D.; Graham, S. McG.; Handley, M.; Latli, B.; Streinz, L.; Tasayco J., M.L. "Enzymatic Processing of Pheromones and Pheromone Analogues". Experientia. 1989, 45, 263‑270. 

Prestwich, G.D.; Vogt, R.G.; Ding, Y.‑S.; Graham, S. McG.; Streinz, L.; Sun, W.‑C.; Tasayco J., M.L.; Webster, F.X. "Disruption of Pheromone Binding and Catabolism: Enzyme Inhibitors and Receptor Affinity Labels". In Endocrinological Frontiers of Physiological Insect Ecology; Sehnal, F.; Zabza, A.; Denlinger, D.L., Eds.; Wroclaw Technical University Press: Wroclaw, Poland, 1988; pp 983‑995.