Guijun WangAssociate Professor – Organic Chemistry
B.S., Tsinghua University 1990 Ph.D., Michigan State University 1999
phone: (504) 280-1258 office: CSB 341 |
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Research Interests Our main research interests are the synthesis of biologically interesting compounds, including the design and synthesis of chiral small molecules and the total synthesis of complex natural products. We are also interested in synthesizing and developing self-assembling supramolecular systems. Overviews of our current projects are shown below: I. Synthesis of Chiral Building Blocks and Medicinally Interesting Compounds Small chiral heterocycles containing N, O, S, etc. are important building blocks for biologically active compounds and drug candidates. For example, compounds 1-6 are important building blocks for synthesizing antibacterial agents, anticoagulants, and other biologically active compounds. We have developed efficient synthetic routes for these compounds starting from S-3-hydroxyl-g-butyrolactone (7), which is derived from starch or lactose. The two main goals for our current and future research are: 1) Exploration of new synthetic methods to chiral small molecules including heterocycles that are useful building blocks for biologically active compounds. 2) Design, synthesis, and evaluation of chiral drug like compound libraries for novel antimicrobial and anticancer agents.
II. Total Synthesis of Natural Products and Their Analogs Aeruginosins are serine protease inhibitors isolated from Microcystis aeruginoso. They are small linear peptides that contain a new bicyclic amino acid core structure containing 2-carboxy-6-hydroxyoctahydroindole (Choi). Aeruginosins are thrombin and factor VIIa inhibitors, and the Choi structure is important for their biological activity. In order to understand the structure-activity relationship and to discover novel thrombosis inhibitors, we have synthesized several analogs of aeruginosin 298-A using different P2 and P1 residues. The second class of compounds we are interested in are the cyclic glycopeptides, mannopeptimycins. Mannopeptimycins and their derivatives are novel antibacterial agents against multi-resistant Gram-positive bacteria. Currently, we are developing methods for the total synthesis of these cyclic glycopeptides.
III. Carbohydrate based self-assembling systems Carbohydrates contain all of the important elements needed to prepare highly functional and synthetically flexible compounds. The creation of novel functional biocompatible materials from naturally abundant carbohydrates is very important for the advancement of carbohydrate chemistry, material science, biotechnology, and the biomedical field. The formation of hydrogels or organogels by small molecules in aqueous or organic solvents can be used for preparing novel materials. In our research, novel carbohydrate based low molecular weight hydrogelators and other functional materials are synthesized and characterized. Their applications in enzyme immobilization and biosensors, as well as controlled release media, are being explored. These novel functional carbohydrate based organogelators are expected to be useful in forming matrices for macromolecule encapsulation and separation, biosensors, chemosensors, and drug delivery. Our research effort should also contribute significantly to biomaterials research in tissue engineering, drug delivery, and bimolecular recognition.
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Positions Available for PhD Graduate Students Multiple graduate assistant positions are available for the Spring and Fall 2012 semesters in the Wang group. The research projects include the synthesis of natural products and their analogs, synthetic methods development, and the study of carbohydrate bases self-assembling systems. Students must be a chemistry major and have an interest in synthetic organic chemistry and/or catalysis, medicinal, and material chemistry. Doctoral graduate assistants will be fully supported by either a TA or RA fellowship. For questions, please contact Dr. Wang at gwang2@uno.edu. Interested students can send application materials directly to Dr. Wang and/or apply through the departmental website: http://chem.uno.edu/ChemistryDepartmentfolder/Apply.html Selected Publications "Synthesis and structural analysis of a series of D-glucose derivatives as low molecular weight gelators” Cheuk, S.; Stevens, E.; Wang, G. Carbohyd. Res. 2009, 344, 417-425. "Regio and stereo selective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions.” Wang, G.; Ella-Menye, J. R.; St. Martin, M.; Yang, H.; Williams, K. Org. Lett. 2008, 10, 4203-4206. “Total synthesis of Aeruginosin 298-A analog.” Nie, X.; Wang, G. Tetrahedron, 2008, 64, 5784-5793. “Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from D-mannose.” Ella-Menye, J.-R.; Nie, X; Wang, G. Carbohyd. Res. 2008, 343, 1743-1753. “Synthesis and antibacterial properties of oxazolidinone and oxazinanones.” Wang, G. Curr. Med. Chem. Anti-infective Agents. 2008, 7, 32-49. “New synthetic methods to chiral 2-oxazolidinones and 1,3-oxazinan-2-ones.” Ella-Menye, J.-R. Wang, G. Tetrahedron, 2007, 63, 10034-10041. “Synthesis and self-assembling properties of diacetylene containing glycolipids.” Nie, X; Wang, G. J. Org. Chem. 2006, 71, 4734-4741. “Design and synthesis of novel chiral 1,3-oxazinan-2-ones as antibacterial agents.” Wang, G.; Ella-Menye, J.-R.; Sharma, V. Bioorg. Med. Chem. Lett. 2006, 16, 2177-2181. “Synthesis and characterization of glucose lipids as hydrogelators” Wang, G.; Sharma, V.; Cheuk, S.; Williams, K.; Dakessian, L.; Thorton, Z. Carbohyd. Res. 2006, 341, 705-716. “Synthesis of a ring oxygenated variant of the 2-carboxy-6-hydroxyoctahydroindole core of Aeruginosin-298 from glucose.” Nie, X.; Wang, G. J. Org. Chem. 2005, 70, 8687-8692. "A New Synthesis of Chiral 1,3-oxazinan-2-ones from Carbohydrate Derivatives," Ella-Menye, J.-R.; Sharma, V.; Wang, G. J. Org. Chem. 2005, 70, 463-469. |
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