Dr Brendan Wilkinson

Lecturer in Organic Chemistry - School of Science and Technology

Brendan Wilkinson

Phone: +61 6773 5653

Email: brendan.wilkinson@une.edu.au

Biography

  • BSc (Hons) Griffith University 2003.
  • PhD Griffith University 2007.
  • EPSRC Post-doctoral research associate, University of Oxford 2007-09.
  • Post-doctoral research associate, The University of Sydney, 2009-12
  • Discovery Early Career Research Fellow, Monash University, 2013-2016.
  • Lecturer in organic chemistry, The University of New England, 2016-present.

Memberships

Royal Australian Chemical Society (MRACI, CCHEM)

Consultancy Interests

I am strongly committed to industry engagement. We have active collaborations within Axieo Australia toward the development of renewable surfactants for food and mining. Supervision of a industry sponsored PhD student is evidence of this commitment.

Teaching Areas

Organic chemistry, bioorganic and medicinal chemistry

Research Interests

1. Carbohydrate biomaterials

  • Synthesis and biomedical applications of photo-switchable carbohydrate-based surfactants and hydrogels.
  • Glycopeptide dendrimers and PDIs as therapeutic and antifreeze agents.

2. Organic synthesis and functional supramolecular materials

  • Dynamic combinatorial chemistry as a tool for the discovery of new chiral catalysts.
  • Template-directed synthesis of cyclodextrin mimics for drug delivery.

3. Bioorganic and medicinal chemistry

  • Rational development of carbohydrate-based cryoprotectants.
  • Dynamic combinatorial chemistry as a tool for screening peptide based therapeutics.
  • Carbohydrate and glycopeptide-based vaccines for neglected tropical diseases.

Our group is interested in the design and synthesis of responsive carbohydrate biomaterials and their biomedical applications. Current areas of research include redox- and photo-responsive sugar surfactants and hydrogels as intelligent drug delivery vectors, self-assembled nanomaterials including glycodendrimers and biofunctionalised perylene diimide dyes as potential therapeutic agents, vaccines and antifreeze agents. We are also interested in developing adaptable carbohydrate and glycopeptide macrocycles as potential drug carriers. Our group collaborates with a number of prominent researchers, including Prof. Robert Ben (Ottawa), Prof. Charl Faul (Bristol), Assoc. Prof. Helen Blanchard (Griffith) and Prof. Vipul Bansal (RMIT).

Recent grants

ARC Discovery Early Career Research Award (DECRA, DE130101673) “Synthesis of biomimetic carbohydrate receptors using dynamic combinatorial chemistry”

Publications

Selected Recent Publications:

  1. Adam, M. K.; Hu, Y.; Poisson, G. S.; Pottage, M. J.; Ben, R. N.; Wilkinson, B. L. Carbohydr. Res. 2017, 439, 1-8.
  2. Hu, Y.; Zou, W.; Julita, V.; Ramanathan, R.; Tabor, R. F.; Nixon-Luke, R.; Bryant, G.; Bansal, V.; Wilkinson, B. L. Chem. Sci. 2016, 7, 6628-6634.
  3. Adam, M. K.; Poisson, J.; Hu, Y.; Prasannakumar, G.; Pottage, M. J.; Ben, R. N.; Wilkinson, B. L. RSC Adv. 2016, 6, 39240-39244.
  4. Hu, Y.; Marlow, J. B.; Ramanathan, R.; Zou, W.; Tiew, H. G.; Pottage, M. J.; Bansal, V.; Tabor, R. F.; Wilkinson, B. L. Synthesis and Properties of Photoswitchable Carbohydrate Fluorosurfactants, Aust. J. Chem. 2015, 68, 1880-1884.
  5. Suthagar, K.; Watson, J. A.; Wilkinson, B. L.; Fairbanks, A. J. Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis, Eur. J. Med. Chem. 2015, 102, 153-166.
  6. Reeks, T.; Jones, A., Brust, A., Sridharan, S., Corcilius, L., Wilkinson, B. L., Thaysen-Andersen, M., Payne, P. J., Kini, R. M., Daly, N. L., Alewood, P. F. A bifunctional O-glycosylated natriuretic peptide, TcNP-a, from the venom of Tropidechis carinatus has a defined alpha helix, Angew. Chem. Int. Ed. 2015, 54, 4828-4831.
  7. Hu, Y., Tabor, R. F., Wilkinson, B. L. Sweetness and Light – design and application of photoswitchable glycoconjugates, Org. Biomol. Chem. 2015, 13, 2216-2225.
  8. Ludeman, J. P., Nazari-Robati, M., Wilkinson, B. L., Huang, C., Payne, R. J., Stone, M. J., Phosphate Modulates Receptor Sulfotyrosine Recognition by the Chemokine Monocyte Chemoattractant Protein-1 (MCP-1/CCL2), Org. Biomol. Chem. 2015, 13, 2162-2169.
  9. Tabor, R. F., Pottage, M. J., Garvey, C. J., Wilkinson, B. L. Light-induced structural evolution of carbohydrate-based surfactant micelles, Chem. Commun. 2015, 51, 5509-5512.
  10. Tabor, R. F., Tan, D. D., Han, S. S., Young, S. A., Seeger, Z. L. E., Pottage, M. J., Garvey, C. J., Wilkinson, B. L. Reversible pH- and photo-controllable carbohydrate-based surfactants, Chem. Eur. J. 2014, 20, 13881-13884.
  11. McDonald, D. M., Wilkinson, B. L., Corcilius, L., Thaysen-Andersen, M., Byrne, S. N., Payne. R. J. Synthesis and immunological evaluation of self-adjuvanting MUC1-macrophage activating lipopeptide 2 conjugate vaccine candidates. Chem. Commun. 2014, 50, 10273-10276.
  12. Huma, Z. E., Ludeman, J. P., Wilkinson, B. L., Payne, R. J., Stone, M. J. NMR characterization of cooperativity: Fast ligand binding coupled to slow protein dimerization. Chem. Sci. 2014, 5, 2783-2788.
  13. Hsieh, Y.S.Y., Wijeyewickrema, L. C., Wilkinson, B. L., Pike, R. N., Payne, R. J. Total synthesis of homogeneous variants of hirudin P6: A post-translationally modified anti-thrombotic leech-derived protein. Angew.Chem. Int. Ed. 2014, 53 (15), 3947-3951.
  14. Al Sheikha, D., Wilkinson, B. L., Santhakumar, G., Thaysen-Andersen, M., Payne, R. J. Synthesis of homogeneous MUC1 oligomers via a bi-directional ligation strategy. Org. Biomol. Chem. 2013, 11, 6090-6096.
  15. Roche, M., Halimi, S., Duncan, R.,Wilkinson, B. L. et. al. A common mechanism of clinical HIV-1 resistance to the CCR5 antagonist maraviroc despite divergent resistance levels and lack of common gp120 resistance mutations. Retrovirology 2013, 10 (43), 1-20.
  16. Wilkinson, B. L. 1-(Acyloxy)benzotriazoles: Useful Reagents for the Regioselective Acylation of Diols. Aust. J. Chem. 2013, 66 (8), 910-912.
  17. Wilkinson, B. L., Day, S., Chapman, R., Perrier, S., Apostolopoulos, V., Payne, R. J. Synthesis and immunological evaluation of self-assembling and self-adjuvanting tricomponent glycopeptide cancer-vaccine candidates. Chem. Eur. J. 2012, 18 (51), 16540-16548.
  18. Hsieh, Y. S. Y., Taleski, D., Wilkinson, B. L., Wijeyewickrema, L. C., Adams, T. E., Pike, R. N., Payne, R. J. Role of O-Glycosylation and Tyrosine Sulfation on Leech-Derived Peptides for Binding and Inhibitory Activity against Thrombin. Chem. Commun. 2012, 48, 1547-1549.
  19. Hsieh, Y.S.Y., Wilkinson, B. L., O'Connell, M. R., MacKay, J. P., Matthews, J. M., Payne, R. J. Synthesis of the bacteriocin glycopeptide sublancin 168 and S-glycosylated variants. Org. Lett. 2012, 14 (7), 1910-1913.
  20. Moeker, J., Teruya, K., Rossit, S., Wilkinson, B. L., Lopez, M., Bornaghi, L. F., Innocenti, A., Supuran, C. T., Poulsen, S. –A. Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases. Bioorg. Med. Chem. 2012, 20 (7), 2392-2404.
  21. Wilkinson, B. L. Stone, R. S., Capicciotti, C. J. Thaysen-Andersen, M., Matthews, J. M., Packer, N. H., Ben, R. N., Payne, R. J.  Total synthesis of homogeneous antifreeze glycopeptides and glycoproteins. Angew. Chem. 2012, 51 (15), 3606-3610.
  22. Wilkinson, B. L., Day, S., Malins, L., Apostolopoulos, V., Payne, R. J.Self-adjuvanting Multi-component Cancer Vaccine Candidates Combining Per-glycosylated MUC1 Glycopeptides and the Toll-like Receptor 2 Agonist Pam3CysSer. Angew. Chem. Int. Ed. 2011, 50, 1635-1639.
  23. Thaysen-Anderson, M., Wilkinson, B. L., Payne, R. J., Packer, N. Site-specific Characterisation of Densely Glycosylated Mucin-type Peptides using Electron Transfer Dissociation ESI-MS/MS. Electrophoresis 2011, 32, 3536–3545.
  24. Barker, M. K., Wilkinson, B. L., Faridmoayer, A., Scaman, C. H., Fairbanks, A. J., Rose, D. R. Protein Expres. Purif. 2011, 79, 96-101.
  25. Wilkinson, B. L., Chun, C. K. Y., Payne, R. J.; Synthesis of MUC1 thioesters and ligation by direct aminolysis. Biopolymers: Pept. Sci. 2011, 96 (2), 137-146.
  26. Wilkinson, B. L., Malins, L. R., Chun, C. K., Payne R. J. Synthesis of MUC1-lipopeptide chimeras. Chem Commun. 2010, 46 (34), 6249-6251.
  27. Wilkinson, B.L.; Bornaghi, L.F. Lopez, M.; Healy, P.C.; Poulsen, S.-A.; Houston, T.A. Synthesis of N-Propargyl Azasugar Scaffolds for Compound Library Generation using Click Chemistry. Aust. J. Chem. 2010, 63, 821-829.
  28. van Dijkum, E.; Danac, R.; Hughes, D.; Wilkinson, B. L.; Fairbanks, A. J. Synthesis of glucose derivatives modified at the 4-OH position as potential chain-terminators of cellulose biosynthesis; herbicidal activity of simple monosaccharide derivatives. Org. Biomol. Chem. 2009, 7, 1097-1105.
  29. Yeoh, K. K.; Butters, T. D.; Wilkinson, B. L.; Fairbanks, A. J. Probing Replacement of Pyrophosphate via Click Chemistry; Synthesis of UDP-Sugar Analogues as Potential Glycosyl Transferase Inhibitors. Carbohydr. Res.2009, 344, 586-591.
  30. Ayers, B.; Wilkinson, B. L.; Sim, E.; Long, H.; Fairbanks, A. J. Stereoselective synthesis of beta-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis. Carbohydr. Res. 2009, 344, 739-746.
  31. Wilkinson, B. L.; Long, H.; Sim, E.; Fairbanks, A. J. Synthesis of Arabino Glycosyl Triazoles as Potential Inhibitors of Mycobacterial Cell Wall Biosynthesis. Bioorg. Med. Chem. Lett. 2008, 18 (23), 6265-6267.
  32. Poulsen S. A.; Wilkinson B. L.; Innocenti A.; Vullo D.; Supuran C. T. Carbonic anhydrase inhibitors: Selective inhibition of the extracellular, tumor-associated isoforms IX and XII over isozymes I and II with glycosyl-thioureido-sulfonamides. Bioorg. Med. Chem. Lett.2008, 18 (16), 4624-7.
  33. Wilkinson, B. L.; Fairbanks, A. J. One-pot synthesis of carbohydrate thionolactones from 1-thiosugars. Tetrahedron Lett. 2008, 49, 4941-4943.
  34. Wilkinson, B. L.; Innocenti A.; Vullo, D; Supuran C. T.; Poulsen, S. –A.; Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides. J. Med. Chem. 2008, 51 (6), 1945-1953.
  35. Wilkinson, B. L., Bornaghi, L. F., Houston, T. A., Innocenti, A., Vullo, D., Supuran, C. T., Poulsen, S. -A. Carbonic anhydrase inhibitors: Inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides. J. Med. Chem. 2007, 50 (7),1651-1657.
  36. Wilkinson, B. L., Bornaghi, L. F., Houston, T. A., Innocenti, A., Vullo, D., Supuran, C. T., Poulsen, S. –A. Inhibition of membrane-associated carbonic anhydrase isozymes IX, XII and XIV with a library of glycoconjugate benzenesulfonamides. Bioorg. Med. Chem. Lett. 2007, 17 (4), 987-992.
  37. Wilkinson, B. L.; Bornaghi, L. F.; Wright, A. D.; Houston, T. A.; Poulsen, S. –A. Antimycobacterial activity of a bis-sulfonamide. Bioorg. Med. Chem. Lett. 2007, 17 (5), 1355-1357.
  38. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Supuran, C. T.; and Poulsen, S. –A. A novel class of carbonic anhydrase inhibitor: glycoconjugate benzene sulfonamides prepared by “click-tailing” J. Med. Chem. 2006, 49 (22), 6539-6548.
  39. Wilkinson, B. L.; Bornaghi, L. F.; Poulsen, S. –A.; Houston, T. A. Synthetic utility of glycosyl triazoles in carbohydrate chemistry Tetrahedron 2006, 62 (34), 8115–8125.
  40. Wilkinson, B. L. B., L.F.; Houston, T. A.; Poulsen, S. -A.; White, A. R. 4-Hydroxymethyl-1-(2',3',4',6'-tetra-O-acetyl-ß-D-glucopyranosyl)-1,2,3-triazole. Acta Crystallographica, Section E: Structure Reports Online 2006, E62, o5065-o5067.
  41. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Poulsen, S. -A, Healy, P. C.   Methyl 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β -D-glucopyranuronate at room temperature.    Acta Crystallographica, Section E: Structure Reports Online 2005, E61(3), o738-o740.
  42. Bornaghi, L. F.; Wilkinson, B.  L.; Kiefel, M. J.; Poulsen, S. -A.   Synthesis of cyclic oligomers of a modified sugar amino acid utilising dynamic combinatorial chemistry. Tetraherdon Lett. 2004, 45 (50), 9281-9284.
  43. Houston, T. A., Wilkinson, B. L., Blanchfield, J. T. Boric acid-catalyzed chemoselective esterification of α -hydroxycarboxylic acids. Org. Lett. 2004, 6 (5), 679-681.

Patents and book chapters:

  1. Wilkinson, B. L.; Day, S.; Apostolopoulos, V.; Payne, R. J. “Glycopeptide cancer vaccine candidates”, 2011, Australian Patent no. 2010905492.
  2. Wilkinson, B. L.; Bornaghi, L. F.; Poulsen S. –A.; Click Chemistry in Carbohydrate Based Drug Development and Glycobiology. Glycobiology Research Trends, 2009, Kaplan, S. P. (Ed.) Nova Science publishers, New York, 127-172.
  3. Wilkinson, B. L.; Bornaghi, L. F.; Poulsen S. –A.; Chapter IV - Click Chemistry in Carbohydrate Based Drug Development and Glycobiology, in Drug Design Research Perspectives, 2007, Kaplan, S. P. (Ed.) Nova Science publishers, New York, 57-102.

Research Supervision Experience

Currently supervising three PhD students.