Guijun Wang, Ph.D.

 

Research interests: Organic Synthesis, Medicinal Chemistry, Carbohydrate Chemistry, Supramolecular Chemistry.

B.S.,   Tsinghua University, Beijing, 1990

M.S.,  Tsinghua University, Beijing, 1993

Ph.D., Michigan State University, 1999

Postdoctoral Associate, Yale University, 2002

Assistant Professor, University of New Orleans, 2002

Associate Professor, University of New Orleans, 2006

 

 

 

 

 

 

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 aeruginosa. 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 this new amino acid 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. Biocompatible functional small molecule hydrogelators derived from carbohydrates and amino acids are of great interest because of the potential applications in drug delivery, tissue engineering, etc. 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.

                            

  

Publications

Research at the University of New Orleans (Wang as corresponding author):

  1. Cheuk, S.; Goyal, N.; Wang, G. “D-Glucosamine derived low molecular weight organogelators: Design, synthesis and characterizations” J. Org. Chem. 2009, manuscript submitted.
  2. Wang, G.; Goyal, N.; Hopkinson, B. “Synthesis and evaluation of aeruginosin analogs as thrombin inhibitors with modification at the P1 position.” Bioorg. Med. Chem. Lett. 2009, 19, 3798-3803.
  3. Wang, G.; Cheuk, S.; Yang, H.; Goyal, N.; Reddy, P. V. N. “Synthesis and characterization of a series of monosaccharide derived carbamates as low molecular hydrogelators.”  Langmuir, 2009, 25, 8696-8705 .
  4. Cheuk, S.; Stevens, E.; Wang, G. “Synthesis and structural analysis of a series of D-glucose derivatives as low molecular weight gelators”   Carbohyd. Res. 2009, 344, 417-425.
  5. Wang, G.; Goyal, N.  “Aeruginosin analogs and other compounds with rigid bicyclic structure as potential antithrombotic agents” Curr. Med. Chem. Cardiovascular Agents.  2009, in press.
  6. Wang, G.; Ella-Menye, J. R.; St. Martin, M.; Yang, H.; Williams, K.  “Regio and stereo selective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions.”  Org.  Lett. 2008, 10, 4203-4206.
  7.  Nie, X.; Wang, G. “Total synthesis of Aeruginosin 298-A analog.” Tetrahedron, 2008, 64, 5784-5793.
  8. Ella-Menye, J.-R.; Nie, X; Wang, G. “Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from D-mannose.” Carbohyd. Res. 2008, 343, 1743-1753.
  9. Wang, G. “Synthesis and antibacterial properties of oxazolidinone and oxazinanones.”  Curr. Med. Chem. Anti-infective Agents. 2008, 7, 32-49.
  10. Ella-Menye, J.-R. Wang, G. “New synthetic methods to chiral 2-oxazolidinones and  1,3-oxazinan-2-ones.” Tetrahedron, 2007, 63, 10034-10041.
  11. Nie, X; Wang, G. “Synthesis and self-assembling properties of diacetylene containing glycolipids.”  J. Org. Chem. 2006, 71, 4734-4741.
  12. Wang, G.; Ella-Menye, J.-R.; Sharma, V.  “Design and synthesis of novel chiral 1,3-oxazinan-2-ones as antibacterial agents.” Bioorg. Med. Chem. Lett. 2006, 16, 2177-2181.
  13. Wang, G.; Sharma, V.; Cheuk, S.; Williams, K.; Dakessian, L.; Thorton, Z. “Synthesis and characterization of glucose lipids as hydrogelators” Carbohyd. Res. 2006, 341, 705-716.
  14. Nie, X.; Wang, G. “Synthesis of a ring oxygenated variant of the 2-carboxy-6-hydroxyoctahydroindole core of Aeruginosin-298 from glucose.” J. Org. Chem. 2005, 70, 8687-8692.
  15. Ella-Menye, J.-R.; Sharma, V.; Wang, G. “A new synthesis of chiral 1,3-oxazinan-2-ones from carbohydrate derivatives.” J. Org. Chem. 2005, 70, 463-469.
  16. Wang, G. “Liposome as drug delivery vehicles.” Book chapter in Delivery issues in drug discovery edited by Binghe Wang, Teruna Siahaan and Rick Soltero. Publisher, John Wiley & Sons, 2005, 411-434.

Publications from postdoctoral and PhD work:

  1. Hollingsworth, R. I.; Wang, G.  “Antibacterials, oxazolidinones.” Kirk-Othmer Encyclopedia of Chemical Technology Review article, 2003.
  2. Wang, G.; Hamilton, A. D.  “Low molecular weight organogelators for water.”  Chem. Comm. 2003, 311-312.
  3. Hollingsworth, R. I.; Wang, G.  “General three carbon chiral synthons from carbohydrates - chiral pool and chiral auxiliary approaches.” ACS symposium series 841, 2002, 85-102. Carbohydrate Synthons in Natural Products Chemistry Edited by Witczak, Z. J and Tatsuta, K.
  4. Wang, G.; Hamilton, A. D.  “Functionalized bisurea derivatives as organic gelators.”  Chem. Eur. J. 2002, 8, 1954-1961.
  5. Wang, G.; Hollingsworth, R. I.  “Offsetting the tubule-forming tendency of chiral diacetylene- containing lipids: planar strips, ribbons and vesicles from a diacetyleneic lipid analog of a thermophilic bacterium.” Adv. Materials 2000, 12, 871-874.
  6. Hollingsworth, R.I.; Wang, G.  “Toward a carbohydrate-based chemistry: progress in the development of general-purpose chiral synthons from carbohydrates.” Chem. Rev. 2000, 100, 4267-4282.
  7. Hollingsworth, R. I.; Wang, G.  “Optically-active three-carbon synthons: another milestone in the creation of a general carbohydrate chiral technology platform.” Chim. Oggi 2000, 18, 40-42.
  8. Wang, G.; Hollingsworth, R. I. “A simple three-step method for preparing homochiral 5-trityloxymethyl-2-oxazolidinones from optically active 3-hydroxy-g-butyrolactones.” Tetrahedron Asymmetry 2000, 11, 4429-4432.
  9. Wang, G.; Hollingsworth, R. I.  “The direct conversion of (S)-3-hydroxy-g-butyrolactone to chiral 3-carbon building blocks.” J. Org. Chem. 1999, 64, 1036-1038.
  10. Wang, G.; Hollingsworth, R. I.  “Synthesis and properties of chiral self-assembling lamellar polydiacetylene systems with very high long-range order.” Langmuir 1999, 15, 3062-3069.
  11. Wang, G.; Hollingsworth, R. I.  “Synthesis and properties of a bipolar, bis-phosphatidyl ethanolamine that forms stable 2-dimensional self-assembled bilayer systems and liposomes.” J. Org. Chem. 1999, 64, 4140-4147.
  12. Wang, G.; Hollingsworth, R. I.  “Synthetic routes to L-carnitine and L-gamma-amino-beta-hydroxybutyric acid from (S)-3-hydroxybutyrolactone by functional group priorities switching.” Tetrahedron Asymmetry 1999, 10, 1895-1901.
  13. Wang, G.; Hollingsworth, R. I.  “Easily accessible uniform wide-diameter helical, cylindrical and nested diacetylene superstructures that can be metallized and oriented in magnetic Fields.” Langmuir 1999, 15, 6135-6138.
  14. Guo, Z.; Wang, G.; Tang Y.; Song, X.  “A crown ether bearing fulgide: the regulation of photochromism by supramolecular effects.” Liebigs Ann. 1997, 941-942.
  15. Wang, G.; Guo, Z.  “The measurement of quantum efficiency of cinamate’s photobromination.” Univ. Chem. (Chinese) 1996, 11, 42-47. 
  16. Guo, Z.; Wang, G.; Tang Y.; Song, X.  “Photokinetic study on the photochromic reaction of aberchrome 540TM on chemical actinometry.”  J. Photochem. Photobiol. A. 1995, 88, 31-34.
  17. Wang, G.  “Study on thermochemical properties of crown-ether and europium (III) host guest complexes.” J. Tsinghua Univ. (Sci & Tech), 1995, 35, 26-30 (Chinese).
  18. Wang, G.; Guo, Z.; Zhang, F.; Zhao, F.; Tang, Y.; Song, X.  “A study on fluorescence characteristics of complexes formed by 4¢-substituted benzo-15-crown-5 and europium (III).”  Chinese J. Chem. Phys, 1995, 8, 331-335 (Chinese).
  19. Wang, G.; Guo, Z.; Zhao, F.  “A convenient synthetic method for 2,5-dimethyfuran.” Chem. Reagents (Chinese) 1995, 17, 182.
  20. Li, Y.; Wang, G.  “ESR study on copper (II) complexes of bis (4¢-benzo-15-crown-5).” Chinese. J. Chem. 1992, 10, 304-308.

List of Patents

  1. Wang, G. “Antibacterial Agents” US-2009-0048240-A1, 2009.
  2. Hollingsworth, R. I.; Wang, G.; Padmakumar, R.; Mao, J.; Zhang, H.; Dai, Z.; Puthuparampil, K. “Process for the Preparation of a Library of Oxazolidinones and Method of Use Thereof.” PCT Int. Appl. WO03106413 A, 2003.
  3. Hollingsworth, R. I.; Wang, G. “Unsaturated Side Chain Polyamide Polymers.” 2003, US6541401. 
  4. Hollingsworth, R. I.; Wang, G. “Process for the Preparation of 5-Hydroxymethyl 2-Oxazolidinone and Novel Intermediate.”  PCT Int. 2002, WO 0224669.
  5. Hollingsworth, R. I.; Wang, G. “5-Trityloxymethyl-oxazolidinones and Process for the Preparation Thereof .”  PCT Int. 2002, WO 0224670.
  6. Hollingsworth, R. I.; Wang, G. Ordered Polyacetylenes and Process for the Preparation Thereof. 2002, US 6388085.
  7. Hollingsworth, R. I.; Wang, G. Ordered Polyacetylenes and Process for the Preparation Thereof. 2002, US 6392110.
  8. Hollingsworth, R. I.; Wang, G. Ordered Polyacetylenes and Process for the Preparation Thereof. 2002, US 6392112.
  9. Hollingsworth, R. I.; Wang, G. Ordered Polyacetylenes and Process for the Preparation Thereof. 2002, US 6395868.
  10. Hollingsworth, R. I.; Wang, G. Ordered Polyacetylenes and Process for the Preparation Thereof. 2002, US 6399842.
  11. Hollingsworth, R. I.; Wang, G. “Ordered Polyacetylenes and Process for the Preparation Thereof.”  2001, 22 pp. US 6194529. 
  12. Hollingsworth, R. I.; Wang, G. “5-Trityloxymethyl-oxazolidinones and Process for the Preparation   Thereof.” 2001, 4 pp, US 6288239.
  13. Hollingsworth, R. I.; Wang, G. “Process for the Preparation of 5-Hydroxymethyl 2-Oxazolidinone and Novel Intermediate.” 2001, 4 pp, US 6288238.
  14. Hollingsworth, R.I.; Wang, G. “Ordered Diacetylene Compounds, Process for the Preparation Thereof, and Process for Manufacture of Films of Polymers Thereof.” PCT Int. Appl. 2000, 59 pp. WO 0056788.
  15. Hollingsworth, R. I.; Wang, G. “4-Cyano-3-hydroxy Butanoyl Hydrazines, Derivatives and Process for the Preparation Thereof.”  PCT Int. Appl. 2000, 23 pp. WO 0071503.
  16. Hollingsworth, R. I.; Wang, G. “Process for the Preparation of Chiral 4-Cyano-3-hydroxybutanoyl Hydrazides and Their Intermediates.” 2000, 9 pp. US 6114566. 
  17. Hollingsworth, R. I.; Wang, G. “Process for the Preparation of Protected 3-Amino-1, 2-dihydroxypropane Acetal and Derivatives Thereof.” 2000, 13 pp, US, 6040464.
  18. Hollingsworth, R. I.; Wang, G. “Process for the Preparation of Protected Dihydroxypropyl Trialkylammonium salts.” 2000, 9 pp, US 6084131.
  19. Hollingsworth, R. I.; Wang, G. “Process for the Preparation of Protected Dihydroxypropyl Trialkylammonium Salts and Derivatives.” PCT Int. Appl. 1999, 31 pp. WO 9962863.
  20. Hollingsworth, R. I.; Wang, G. “Process for the Preparation of Protected 3-Amino-1, 2-dihydroxypropane Acetal and Derivatives.”  PCT Int. Appl. 1999, 29 pp. WO 9962861.

 

Current group members:

Graduate students:
Kristopher Williams
Navneet Goyal
Michael St. Martin
Hao Yang
Bargav Bharatkumar Parikh
Sanjeeva Reddy Dodlapati

Undergraduate students:
Corey Hampton, Robert Skatenborghs

Former group members:

Postdoctoral associates:
Vibha Sharma
Xiaoping Nie
PVN Reddy

Ph.D. graduate students:
Jean Rene Ella-Menye (Ph.D. 2007)
Sherwin Cheuk (Ph.D. 2008)

Undergraduate students trained (from UNO unless otherwise mentioned):
Corey Hampton, Sherman Coleman (Dillard University, REU), Norshanda Calais ( Xavier Univeristy), Chien Tsao, Branden Hopkinson, Clarence Anglin, Jeffery Draggich, Jennifer Vu, Sean D. Giblin, Emmanuelle Sebha (University of Pasteur, France), Crystal Simons, Chloe Evans (Xavier University, REU student)
Zeus Thornton, Michael St. Martin, Lousi Dakessian, Kristopher Williams.

 

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