The University of Western Australia

UWA Staff Profile

Ipsum Lorem

Keith Stubbs

Assoc/Prof Keith Stubbs

Associate Professor
Molecular Sciences, School of

Contact details
School of Molecular Sciences
The University of Western Australia (M313)
35 Stirling Highway
6488 2725 (office) / 6488 4479 (lab)
+61 8 6488 1005
Room 414, Bayliss Building, Perth campus
BSc PhD W.Aust.
Dr Keith Stubbs completed his undergraduate and PhD studies at UWA, followed by a two year post-doctoral position at Simon Fraser University in Vancouver, Canada. He is now a principal investigator of a research laboratory in the School of Molecular Sciences at UWA. He has held various prestigious research fellowships over his career and he is currently an Associate Professor and Senior Research Fellow.
Key research
Carbohydrates are present in every living system from prokaryotes to eukaryotes and traditionally, have been known for their role in the structural integrity of plants and as energy sources. Recently, however, carbohydrates have been shown to be involved in a variety of fundamental biological processes such as protein folding and trafficking, as well as cellular signaling and recognition. As we gain greater understanding into the roles that carbohydrates play at the cellular level, scientists are faced with new challenges. On the chemistry side, unique carbohydrate-based tools need to be developed and in turn used to investigate the specific roles that a single mono- or polysaccharide plays in the dynamics of the cell in order to keep up with the biochemical discovery of new glycan structures and the enzymes that regulate them. My research aims are to address the development of such tools which involves synthetic, medicinal and biochemical approaches.
Very brief overviews of current research areas are outlined below.
Developing tools to study carbohydrate-processing enzymes in human health and disease: Various human diseases are caused by improper function of a specific carbohydrate-processing enzyme. We aim to develop tools to study these enzymes and then use the information gathered to produce therapeutics. This is done through the use of synthetic and medicinal chemistry approaches. We have numerous collaborators in Canada and the UK working with us on these projects.
Investigations into human milk oligosaccharides: One class of carbohydrates is those found in human breast milk and are termed human milk oligosaccharides (HMOs). These compounds are critical for infant health as they provide nutrition for bifidobacteria (found in the human intestinal tract) which provide great benefits to infants such as nutrients, prevention of pathogenic bacterial growth and suppression of inflammatory and allergic responses. To date though, limited chemical tools have been generated to study these fundamentally important molecules. We have several collaborators in Japan working with us on this project.
Antimicrobial resistance: As the threat of antibiotic resistance grows with each passing year new therapeutic targets are required. We have numerous targets and approaches to developing new therapeutics. This is done through the use of synthetic and medicinal chemistry approaches. We have numerous collaborators in Australia and Canada working with us on these projects.
Investigations into the mechanism and biochemistry of carbohydrate-processing enzymes involved in plant cell wall degradation: Of increasing interest is how bacteria utilise plant-based materials and their direct importance to humans, as we are only able to utilise these carbohydrates for metabolism due to the action of unique enzymes produced by the bacteria living in our gastrointestinal tract. We have numerous collaborators in Canada and the UK working with us on these projects.
Herbicide resistance: The development and use of herbicides in agriculture has improved crop yields worldwide, but like antimicrobial resistance, herbicide resistance is also highly prevalent and is threatening food production. In collaboration with Professor Joshua Mylne (UWA) we have discovered new compounds with herbicidal potency and methods to assess the ability of these compounds to act as herbicides in the field. This project offers exciting opportunities in synthetic organic and medicinal chemistry.
Microfluidics: The development of new methodology in organic chemistry is always required to improve reaction yields and discover new reactions. In collaboration with Professor Colin Raston we have a microfluidic platform that can be utilized to explore new chemical reactions and also develop methodology to improve on existing methodologies. This project offers exciting opportunities in general synthetic organic chemistry.
The laboratory is always very welcoming for people interested in chemistry and/or biochemistry. If you have any interests in these areas please feel free to contact me by email and I am happy to discuss the exciting opportunities available.
Book Chapters

(4) Travis Coyle, Mark B. Richardson, Mitchell Hattie, Keith A. Stubbs, General Preparation of Imidazole-1-sulfonate Esters, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 2, CRC Press, 2014.

(3) Keith A. Stubbs, David J. Vocadlo, Functional proteomic profiling of glycan processing enzymes. Methods in Enzymology, 2006, 415, 253.

(2) Keith A. Stubbs, Robert V. Stick, Contribution for Electronic Encyclopedia of Reagents for Organic Synthesis; Silver Trifluoromethanesulfonate, Wiley Interscience, London, 2004.

(1) Keith A. Stubbs, Robert V. Stick, Contribution for Electronic Encyclopedia of Reagents for Organic Synthesis; Iodine Monochloride, Wiley Interscience, London, 2004.

Journal Articles

(97) Corral, M.G., Leroux, J., Tresch, S., Newton, T., Stubbs, K.A.* and Mylne, J.S., A herbicide structure-activity analysis of the antimalarial lead compound MMV007978 against Arabidopsis thaliana. Accepted to Pest Management Science, 2018.

(96) Moroz, O.V., Sobala, L., Blagova, E., Coyle, T., Wei, P., Morkeberg Krogh, K.B.R., Stubbs, K.A., Wilson, K.S. and Davies, G.J., Structure of a Talaromyces pinophilus GH62 Arabinofuranosidase in complex with AraDNJ at 1.25 Å resolution. Accepted to Acta Crystallography Section F. Structural Biology Communications, 2018.

(95) Ficko-Blean, E., Préchoux, A., Thomas, F., Rochat, T., Larocque, R., Zhu, Y., Stam, M., Génicot, S., Jam, M., Calteau, A., Viart, B., Ropartz, D., Pérez-Pascual, D., Correc, G., Matard-Mann, M., Stubbs, K.A., Rogniaux, H., Jeudy, A., Barbeyron, T., Médigue, C., Czjzek, M., Vallenet, D., McBride, M.J., Duchaud, E. and Michel, G., Carrageenan catabolism is encoded by a complex regulon in marine heterotrophic bacteria. Nature Communications, 2017, 8, 1685.

(94) Corral, M.G., Leroux, J., Tresch, S., Newton, T., Stubbs, K.A.* and Mylne, J.S., Exploiting the evolutionary relationship between malarial parasites and plants to develop new herbicides. Angewandte Chemie International Edition, 2017, 56, 9881.

(93) Debowski, A.W., Walton, S.M., Chua, E.G., Tay, A.C., Liao, T., Lamichhane, B., Himbeck, R., Stubbs, K.A., Marshall, B.J., Fulurija, A. and Benghezal, M., Helicobacter pylori gene silencing in vivo demonstrates urease is essential for chronic infection. PLoS Pathogens, 2017, 13, e1006464.

(92) Yap, H., Muria-Gonzalez, M.J., Kong, B., Stubbs, K.A., Tan, C., Ng, S., Tan, N., Solomon, P.S., Fung, S. and Chooi, Y., Heterologous expression of cytotoxic sesquiterpenoids from the medicinal mushroom Lignosus rhinocerotis in yeast. Microbial Cell Factories, 2017, 16, 103.

(91) Britton J, Stubbs K.A., Weiss G.A. and Raston C.L., Vortex Fluidic Chemical Transformations. Chemistry - A European Journal, 2017, 23, 13270.

(90) Sato, M., Liebschner, D., Yamada, Y., Matsugaki, N., Arakawa, T., Wills, S.S., Hattie, M., Stubbs, K.A., Ito, T., Senda, T., Ashida, H. and Fushinobu, S., The first crystal structure of a family 129 glycoside hydrolase from a probiotic bacterium reveals critical residues and metal cofactors. Journal of Biological Chemistry, 2017, 292, 12126.

(89) Hong, L., Yang, T., Liao, T., Debowski, A.W., Nilsson, H., Dell, A., Stubbs, K.A., Marshall, B.J. and Benghezal, M., Insights from the Redefinition of Helicobacter pylori Lipopolysaccharide O-antigen and Core-oligosaccharide Domains. Microbial Cell, 2017, 4, 175.

(88) Vadlamani, G., Stubbs, K.A., Desire, J., Bleriot, Y., Vocadlo, D.J. and Mark, B.L., Conformational flexibility of the glycosidase NagZ allows it to bind structurally diverse inhibitors to suppress b-lactam antibiotic resistance. Protein Science, 2017, 26, 1161.

(87) Hong, L., Yang, T., Liao, T., Debowski, A.W., Nilsson, H., Fulurija, A., Haslam, S.M., Mulloy, B., Dell, A., Stubbs, K.A., Marshall, B.J. and Benghezal, M., The Redefinition of Helicobacter pylori Lipopolysaccharide O-antigen and Core-oligosacharide Domains. PLoS Pathogens, 2017, 13, e1006280.

(86) Coyle, T., Debowski, A.W., Varrot, A. and Stubbs, K.A.*, Exploiting sp2-hybridization in the development of potent 1,5-a-L-arabinanase inhibitors. ChemBioChem, 2017, 18, 974.

(85) Corral, M.G., Leroux, J., Stubbs, K.A. and Mylne, J.S., Herbicidal properties of antimalarial drugs. Scientific Reports, 2017, 7, 45871.

(84) Yamada, C., Gotoh, A., Sakanaka, M., Hattie, M. Stubbs, K.A., Katayama-Ikegami, A.,Hirose, J., Kurihara, S., Arakawa, T., Kitaoka, M., Okuda, S., Katayama, T. and Fushinobu, S., Evolutionary insight into symbiosis between Bifidobacterium longum and breast-fed infants gained by molecular analysis of lacto-N-biosidase. Cell Chemical Biology, 2017, 24, 515.

(83) Bartley, S.N., Mowlaboccus, S., Mullally, C., Stubbs, K.A., Vrielink, A., Maiden, M.C.J., Harrison, O.B., Perkins, T.T. and Kahler, C.M., Acquisition of the capsule locus by horizontal gene transfer in Neisseria meningitidis is often accompanied by the loss of UDP-GalNAc synthesis. Scientific Reports, 2017, 7, 44442.

(82) Anandan, A., Evans, G.L., Condic-Jurkic, C., O’Mara, M.L., John, C.M., Phillips, N.J., Jarvis, G.A., Wills, S.S., Stubbs, K.A., Moraes, I., Kahler, C.M. and Vrielink, A., Structure of a lipid A phosphoethanolamine transferase suggests how conformational changes govern substrate binding. Proceedings of the National Academy of Sciences USA, 2017, 114, 2218.

(81) Hong L., Debowski, A.W., Liao, T., Tang, H., Nilsson, H., Marshall, B.J., Stubbs, K.A. and Benghezal, M., Understanding protein glycosylation pathways in bacteria. Future Microbiology, 2017, 12, 59.

(80) Hamou-Segarra, M., Zamorano, L., Vadlamani, G., Chu, M., Sánchez-Diener, I., Juan, C., Blazquez, J., Hattie, M., Stubbs, K.A., Mark, B. and Oliver, A., Synergistic activity of fosfomycin, β-lactams and peptidoglycan recycling inhibition against P. aeruginosa. Journal of Antimicrobial Chemotherapy, 2017, 72, 448.

(79) Ho, L.A., Raston, C.L. and Stubbs, K.A.*, Transition metal free cross coupling reactions in dynamic thin films in accessing pyrimidine and quinoxaline analogues. European Journal of Organic Chemistry, 2016, 5957.

(78) Perley-Robertson, G.E., Yadav, A., Winogrodzki, J., Stubbs, K.A., Mark, B.L. and Vocadlo, D.J., A Fluorescent Transport Assay Enables Study of AmpG Permeases Involved in Peptidoglycan Recycling and Antibiotic Resistance. ACS Chemical Biology, 2016, 11, 2626.

(77) Hemsworth, G.R., Thompson, A.J., Stepper, J. Sobala, L.F., Coyle, T., Larsbrink, J., Spadiut, O., Goddard-Borger, E.D.. Stubbs, K.A., Brumer, H. and Davies, G.J., Structural Dissection of the Bacteroides ovatus xyloglucan PUL. Open Biology, 2016, 6, 160142.

(76) Hattie, M., Cekic, N., Debowski, A.W., Vocadlo, D.J. and Stubbs, K.A.*, Modifying the phenyl group of PUGNAc: Reactivity tuning to deliver selective inhibitors for N-acetyl-D-glucosaminidases. Organic and Biomolecular Chemistry, 2016, 14, 3193.

(75) Cekic, N., Heinonen, J.E., Stubbs, K.A., Roth, C., He, Y., Bennet, A.J., McEachern, E.J., Davies, G.J. and Vocadlo, D.J., Analysis of transition state mimicry by tight binding aminothiazoline inhibitors provides insight into catalysis by human O-GlcNAcase. Chemical Science, 2016, 7, 3742.

(74) Hong, L., Liao, T., Debowski, A.W., Tang, H., Nilsson, H., Stubbs, K.A., Marshall, B.J. and Benghezal, M., Lipopolysaccharide Structure and Biosynthesis in Helicobacter pylori. Helicobacter, 2016, 21, 445.

(73) Harrison, F., McAuliffe, R., Romero, J., Stubbs, K.A. and Oldham, C.E., Fluorescence application to hydrocarbon monitoring in North West Shelf marine waters. APPEA Journal, 1. 345.

(72) Debowski, A.W., Sehnal, M., Liao, T., Stubbs, K.A., Marshall, B.J., Benghezal, M., Expansion of the tetracycline dependent regulation toolbox for Helicobacter pylori. Applied and Environmental Microbiology, 2015, 81, 7969. SPOTLIGHT ARTICLE

(71) Hattie, M., Ito, T., Debowski, A.W., Arakawa, T., Katayama, T., Yamamoto, K., Fushinobu, S. and Stubbs, K.A.*, Gaining insight into the catalysis by GH20 lacto-N-biosidase using small molecule inhibitors and structural analysis. Chemical Communications, 2015, 51, 15008.

(70) Kampmann, S.S., Skelton, B.W., Yeoh, G.C., Abraham, L.J, Lengkeek, N.A., Stubbs, K.A., Heath, C.H. and Stewart, S.G., The synthesis and fluorescence profile of novel thalidomide analogues. Tetrahedron, 2015, 71, 8140.

(69) Watson, M.E., Diepeveen, L.A., Stubbs, K.A. and Yeoh, G.C., Glycosylation-related diagnostic and therapeutic drug target markers in hepatocellular carcinoma. Journal of Gastrointestinal and Liver Diseases, 2015, 24, 349.

(68) Coyle, T., Brumer, H. and Stubbs, K.A.*, An improved preparation of some aryl α-L-arabinofuranosides for use as chromogenic substrates for α-L-arabinofuranosidases. Canadian Journal of Chemistry, 2015, 93, 1176.

(67) Gandy, M.N., Raston, C.L., and Stubbs, K.A.*, Photoredox catalysis under shear using thin film vortex microfluidics. Chemical Communications, 2015, 51, 11041.

(66) Gandy, M.N., Corral, M.G., Mylne, J.S. and Stubbs, K.A.*, An interactive database to explore herbicide physicochemical properties. Organic and Biomolecular Chemistry, 2015, 13, 5586. (Cover Issue)

(65) Gandy, M.N., Byrne, L. and Stubbs, K.A.*, A Simple and Robust Preparation of N-Acetylindoxyls: Precursors for Indigogenic Substrates. Organic and Biomolecular Chemistry, 2015, 13, 905.

(64) Eggers, P.K., Eroglu, E., Becker, T., Chen, X., Vimalanathan, K., Stubbs, K.A., Smith, S.M. and Raston, C.L., Nitrate uptake by p-phosphonic acid or p-(trimethylammonium)methyl calix[8]arene stabilized laminar materials. RSC Advances, 2014, 4, 48348.

(63) Piek, S., Wang, Z., Ganguly, J., Lakey, A.M., Bartley, S.N., Mowlaboccus, S., Anandan, A., Stubbs, K.A., Scanlon, M.J., Vrielink, A., Azadi, P., Carlson, R.W. and Kahler, C.M., The Role of Oxidoreductases in Determining the Function of the Neisserial Lipid A Phosphoethanolamine Transferase Required for Resistance to Polymyxin. PloS One. 2014, 9, e106513.

(62) Singh, A.K., Pluvinage, B., Higgins, M.A., Dalia, A.B., Woodiga, S., Flynn, M., Lloyd, A.R., Weiser, J.N. Stubbs, K.A., Boraston, A.B. and King, S.J., Unraveling the multiple functions of the architecturally intricate Streptococcus pneumoniae β-galactosidase, BgaA, PLoS Pathogens, 2014, 10, e1004364.

(61) Yasmin, L., Eggers, P.K., Skelton, B.W., Stubbs, K.A., and Raston, C.L., Thin film microfluidic synthesis of fluorescent highly substituted pyridines. Green Chemistry. 2014, 16, 3450.

(60) Gandy, M.N., Raston, C.L., and Stubbs, K.A.*, Towards Aryl C-N bond formation in dynamic thin films. Organic and Biomolecular Chemistry, 2014, 12, 4594.

(59) Stubbs, K.A.*, Activity-Based Proteomic Probes for Carbohydrate-Processing Enzymes: Current Trends and Future Outlook. Carbohydrate Research, 2014, 390, 9. TOP 25 HOTTEST ARTICLE FOR 2014.

(58) Yasmin, L. Stubbs, K.A., and Raston, C.L., Vortex fluidic promoted Diels-Alder reaction in an aqueous medium. Tetrahedron Letters, 2014, 55, 2246.

(57) Clayton, E., Hattie, M. Debowski, A.W. and Stubbs, K.A.*, The Synthesis of Carbohydrate-Based Natural Products from Leonurus japonicus and their biological evaluation as anti-oxidants. The Australian Journal of Chemistry, 2014, 67, 1461-1470.

(56) Kim, R.Q., Offen, W.A., Davies, G.J., and Stubbs, K.A., Structural Enzymology of H. pylori Methylthioadenosine Nucleosidase in the Futalosine Pathway. Acta Crystrallography Section D. Biological Chemistry, 2014, D70, 177.

(55) Yasmin, L., Coyle, T., Stubbs, K.A., and Raston, C.L., Stereospecific synthesis of resorcin[4]arenes and pyrogallol[4]arenes in dynamic thin films. Chemical Communications, 2013, 49, 10932.

(54) Pluvinage, B., Stubbs, K.A., Hattie, M. Vocadlo, D.J., and Boraston, A.B., Inhibition of the family 20 glycoside hydrolase catalytic modules in the Streptococcus pneumoniae exo-beta-D-N-acetylglucosaminidase, StrH. Organic and Biomolecular Chemistry, 2013, 11, 7907.

(53) Yasmin, L., Chen, X., Stubbs, K.A., and Raston, C.L., Optimising a vortex fluidic device for controlling chemical reactivity and selectivity. Nature Scientific Reports, 2013, 3, 2282.

(52) Stubbs, K.A.*, Bacik, J., Perley-Robertson, G.E., Whitworth, G.E., Gloster, T.M. Vocadlo, D.J., and Mark, B.L., The Development of Selective Inhibitors of NagZ: Increased Susceptibility of Gram-negative Bacteria to beta-lactams. ChemBioChem, 2013, 14, 1973.

(51) James, E., Eggers, P.K., Harvey, A.R., Dunlop, S.A., Fitzgerald, M., Stubbs, K.A., and Raston, C.L., Antioxidant phospholipid calix[4]arene mimics as micellular delivery systems. Organic and Biomolecular Chemistry, 2013, 11, 6108.

(50) Wanty, C., Anandan, A., Piek, S., Walshe, J., Ganguly, J., Carlson, R.W., Stubbs, K.A., Kahler, C.M., and Vrielink, A. The structure of the Neisserial Lipooligosaccharide phosphoethanolamine transferase A (LptA) required for resistance to polymyxin. The Journal of Molecular Biology, 2013, 425, 3389.

(49) Smith, N.E., Tie, W.J., Flematti, G.R., Stubbs, K.A., Corry, B., Attwood, P.V. and Vrielink, A. Mechanism of the Dehydrogenase Reaction of DmpFG and Analysis of Inter-Subunit Channeling Efficiency and Thermodynamic Parameters in the Overall Reaction. The International Journal of Biochemistry & Cell Biology, 2013, 45, 1878.

(48) Clemons, T.D., Fitzgerald, M., Dunlop, S.A., Harvey, A.R., Iyer, K.S and Stubbs, K.A.* An improved methodology for the spectrophotometric determination of chondroitinase ABC activity. New Journal of Chemistry, 2013, 37, 1944.

(47) Ito, T., Katayama, T., Hattie, M., Sakurama, H., Wada, J., Suzuki, R., Ashida, H., Wakagi, T., Yamamoto, K., Stubbs, K.A., and Fushinobu S. Crystal structures of a glycoside hydrolase family 20 lacto-N-biosidase from Bifidobacterium bifidum. Accepted to The Journal of Biological Chemistry, 2013, 288, 11795.

(46) Bacik, J., Whitworth, G.E., Stubbs, K.A., Vocadlo, D.J., and Mark, B.L. Active site plasticity within the glycoside hydrolase NagZ underlies a dynamic mechanism of substrate distortion. Chemistry and Biology, 2012, 19, 1471.

(45) Macauley, M.S., Chan, J., Zandberg, W.F., He, Y., Whitworth, G.E., Stubbs, K.A., Yuzwa, S.A., Bennet, A.J., Varki, A., Davies, G.J., and Vocadlo, D.J. Metabolism of vertebrate amino sugars with N-glycolyl groups: intracellular O-GlcNGc, UDP-GlcNGc, and the biochemical and structural rationale for the substrate tolerance of O-GlcNAcase. Journal of Biological Chemistry, 2012, 287, 28882.

(44) Eggers, P.K., Becker, T., Melvin, M.K., Boulos, R., James, E., Morellini, N., Harvey, A.R., Dunlop, S.A., Fitzgerald, M., Stubbs, K.A., and Raston, C.L. Composite fluorescent vesicles based on ionic and cationic amphiphilic calix[4]arenes. RSC Advances, 2012, 2, 6250.

(43) Hattie, M., Debowski, A.W., and Stubbs, K.A.* Development of Tools to Study Lacto-N-biosidase: An Important Enzyme Involved in the Breakdown of Human Milk Oligosaccharides. ChemBioChem, 2012, 13, 1128.

(42) Martin, A.D., Houlihan, E., Morellini, N., Eggers, P.K., James, E., Stubbs, K.A., Harvey, A.R., Fitzgerald, M., Dunlop, S.A. and Raston, C.L. Synthesis and toxicology of p-phosphonic acid calixarenes and O-alkylated analogues as potential calixarene-based phospholipids. ChemPlusChem, 2012, 77, 308.

(41) Sumida, T., Stubbs, K.A.*, Ito, M. and Yokoyama, S. Gaining insight into the inhibition of glycoside hydrolase family 20 exo-beta-N-acetylhexosaminidases using a structural approach. Organic and Biomolecular Chemistry, 2012, 10, 2607.

(40) Yeung S.Y., Kampmann, S. Stubbs, K.A., Skelton, B.J., Kaskow, B.J., Abraham, L. and Stewart, S.G. Novel Thalidomide Analogues with Potent NFKB and TNF expression Inhibition. MedChemComm, 2011, 2, 1073.

(39) Clemons, T.D., Evans, C.W. Zdyrko, B., Luzinov, I., Fitzgerald, M., Dunlop, S.A., Harvey, A.R., Iyer, K.S. and Stubbs, K.A.* A general Multifunctional nanoadditives for thermodynamic and kinetic stabilization of enzymes. Nanoscale, 2011, 3, 4085.

(38) Paterson, S.M., Clark, J., Stubbs, K.A.*, Chirila, T.V., and Baker, M.V. Carbohydrate-based crosslinking agents: Potential uses in hydrogels. The Journal of Polymer Science Part A: Polymer Chemistry, 2011, 49, 4312.

(37) Moréra, S., Vigouroux, A., and Stubbs, K.A.* A potential fortuitous binding of inhibitors of inverting family GH9 beta-glycosidase derived from isofagomine. Organic and Biomolecular Chemistry, 2011, 9, 5945.

(36) Martin, A.D., Boulos, R.A., Stubbs, K.A., Raston, C.L. Phosphonated calix[4]arene-based amphiphiles as scaffolds for fluorescent nano-fibres. Chemical Communications, 2011, 47, 7329.

(35) Gandy, M.N., Debowski, A.W., and Stubbs, K.A.* A general method for affinity-based proteomic profiling of exo-alpha-glycosidases. Chemical Communications, 2011, 47, 5037.

(34) Bacik, J.P., Whitworth, G.E., Stubbs, K.A., Yadav, A.K., Martin, D.R., Bailey-Elkin, B.A., Vocadlo, D.J., and Mark, B.L. Molecular Basis of 1,6-Anhydro Bond Cleavage and Phosphoryl Transfer by Pseudomonas aeruginosa 1,6-Anhydro-N-acetylmuramic Acid Kinase. Journal of Biological Chemistry, 2011, 286, 12283.

(33) He, Y., Bubb, A.K., Stubbs, K.A., Gloster, T.M., and Davies, G.J. Inhibition of bacterial O-GlcNAcase by lactone and lactam derivatives: structural, kinetic and thermodynamic analyses. Amino Acids. 2011, 40, 829.

(32) Gandy, M.N., Piggott, M.J. and Stubbs, K.A.*, An Expeditious Synthesis of Iminosugars. The Australian Journal of Chemistry, 2010, 63, 1409. (Cover Issue)

(31) Tognetti, V.B., Van Aken, O., Morreel, K., Vandenbroucke, K., van de Cotte, B., De Clercq, I., Chiwocha, S., Fenske, R., Prinsen, E., Boerjan, W., Gentye, B., Stubbs, K.A., Inze, D., and van Breusegem, F., Perturbation of indole-3-butyric acid homeostasis by the UDP-glucosyltransferase UGT74E2 modulates Arabidopsis architecture and water stress tolerance. The Plant Cell, 2010, 22, 2660.

(30) Macauley, M.S., He, Y., Gloster, T.G, Stubbs, K.A., Davies, G.J., and Vocadlo, D.J., Inhibition of OGA using a Potent and Cell Permeable Inhibitor of O-GlcNAcase does not Induce Insulin Resistance in 3T3-L1 Adipocytes. Chemistry and Biology. 2010, 17, 937.

(29) Stewart S.G., Braun C.J., Polomska M.E., Karimi M., Abraham L.J., Stubbs K.A., Efforts toward elucidating Thalidomide's molecular target: an expedient synthesis of the first Thalidomide biotin analogue. Organic and Biomolecular Chemistry, 2010, 8, 4059.

(28) Goddard-Borger, E.D., and Stubbs, K.A.*, An Improved route to PUGNAc and its Galacto-configured Congener. The Journal of Organic Chemistry, 2010, 61, 3931.

(27) Gunasekara, S. Vrielink, A. and Stubbs, K.A.*, Preliminary Studies into the Inhibition of the Cholesterol alpha-glucosyltransferase from Helicobacter pylori Using Azasugars. Carbohydrate Research, 2010, 345, 960.

(26) He Y., Macauley M.S., Stubbs K.A., Vocadlo D.J., Davies G.J. Visualizing the reaction coordinate of an O-GlcNAc hydrolase. Journal of the American Chemical Society, 2010, 132, 1807.

(25) Pluvinage, B., Ghinet, M.G., Brzezinski, R., Boraston, A.B., and Stubbs, K.A.* Inhibition of the exo-beta-D-glucosaminidase CsxA by a glucosamine-configured castanospermine and an amino-australine analogue. Organic and Biomolecular Chemistry, 2009, 7, 4169.

(24) Stubbs, K.A.*, and Vocadlo, D.J. Affinity-based Proteomics Probes; Tools for studying Carbohydrate-processing Enzymes. Australian Journal of Chemistry, 2009, 62, 521.

(23) Balcewich, M., Stubbs, K.A., He, Y., James, T., Davies, G.J. Vocadlo D.J., and Mark B.L. Insight into a strategy for attenuating AmpC-mediated beta-lactam resistance: structural basis for selective inhibition of the glycoside hydrolase NagZ. Protein Science, 2009, 18, 1541.

(22) Asgarali, A., Stubbs, K.A., Oliver, A., Vocadlo D.J., and Mark B.L. Inactivation of the glycoside hydrolase NagZ attenuates anti-pseudomonal beta-lactam resistance in Pseudomonas aeruginosa. Antimicrobial Agents and Chemotherapy, 2009, 53, 2274.

(21) Stubbs, K.A.*, Macauley, M.S., Vocadlo, D.J. A selective inhibitor of human lysosomal beta-hexosaminidases: Gal-PUGNAc modulates levels of the ganglioside GM2 in neuroblastoma cells. Angewandte Chemie International Edition, 2009, 48, 1300.

(20) Scaffidi A., Stubbs K.A.*, Vocadlo D.J., Stick R.V. The Synthesis and Biological Evaluation of Some Carbocyclic Analogues of PUGNAc. Carbohydrate Research, 2008, 343, 2744.

(19) Yuzwa, S.A., Macauley M.S., Heinonen, J.E., Shan, X., Dennis R.J., Whitworth G.E., Stubbs K.A., McEachern E.J., Davies G.J., Vocadlo D.J. A potent mechanism-inspired O-GlcNAcase inhibitor that blocks phosphorylation of tau in vivo. Nature Chemical Biology, 2008, 4, 483.

(18) Ficko-Blean E., Stubbs K.A., Berg O., Vocadlo D.J., Boraston A.B. Structural and mechanistic insight into the basis of mucopolysaccharidosis IIIB. Proceedings of the National Academy of Sciences USA, 2008, 105, 6560.

(17) Choudbar, N., Bhat, R. G., Stubbs, K.A., Yuzwa, S, Pinto, B.M. Synthesis of 2-Amido, 2-Amino, and 2-Azido derivatives of the nitrogen analogue of the naturally occurring glycosidase inhibitor salacinol and their inhibitory activities against O-GlcNAcase and NagZ enzymes. Carbohydrate Research, 2008, 343, 1766.

(16) Stubbs K.A., Scaffidi A., Debowski A.W., Mark B.L., Stick R.V., Vocadlo D.J. Synthesis and use of mechanism-based protein-profiling probes for retaining b-D-glucosaminidases facilitate identification of Pseudomonas aeruginosa NagZ. Journal of the American Chemical Society, 2008, 130, 327.

(15) Scaffidi A., Stubbs K.A.*, Dennis R.J., Taylor E.J., Davies G.J., Vocadlo D.J., Stick R.V. A 1-Acetamido Derivative of 6-Epivalienamine: An Inhibitor of a Diverse Group of beta-N-acetylglucosaminidases. Organic and Biomolecular Chemistry, 2007, 5, 3013.

(14) Stubbs K.A., Balcewich M., Mark B.L., Vocadlo D.J. Small molecule inhibitors of a glycoside hydrolase attenuate inducible AmpC mediated beta-lactam resistance. Journal of Biological Chemistry, 2007, 282, 21382.

(13) Scaffidi, A., Stick, R.V., Stubbs, K.A. Synthesis of Some Glycosylated Derivatives of 2-Deoxy-2-fluoro-beta-laminaribiosyl Fluoride: Another Success for Glycosynthases. Australian Journal of Chemistry, 2007, 60, 83.

(12) Whitworth G.E., Macauley M.S., Stubbs K.A., Dennis R.J., Davies G.J., Greig I.R., Vocadlo D.J. Analysis of PUGNAc and NAG-thiazoline as Transition State Analogues for Human O-GlcNAcase: Mechanistic and Structural Insights into Inhibitor Selectivity and Transition State Poise. Journal of the American Chemical Society, 2007, 129, 635.

(11) Dennis R.J., Taylor E.J., Macauley M.S., Stubbs K.A., Turkenburg J.P., Hart S.J., Black G.N., Vocadlo D.J., Davies G.J. Structure and mechanism of a bacterial beta-glucosaminidase having O-GlcNAcase activity. Nature Structural and Molecular Biology, 2006, 13, 365.

(10) Stubbs, K.A., Zhang N., Vocadlo, D.J. A rapid and divergent synthesis of 2-acyl derivatives of PUGNAc. Potent and selective inhibitors of O-GlcNAcase. Organic and Biomolecular Chemistry, 2006, 4, 839.

(9) Stubbs, K.A., Macauley, M.A., Vocadlo, D.J. A Simple and Concise Synthesis of Aryl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides. Carbohydrate Research, 2006, 341, 1764.

(8) Cetinbas, N., Macauley, M.A., Stubbs, K.A., Drapala, R., Vocadlo D.J. Identification of Asp174 and Asp175 as the key catalytic residues of human O-GlcNAcase by functional analysis of site-directed mutants. Biochemistry, 2006, 45, 3835.

(7) Macauley, M.A., Stubbs, K.A., Vocadlo, D.J. O-GlcNAcase catalyzes cleaveage of thioglycosides without general acid catalysis. Journal of the American Chemical Society, 2005, 127, 17202.

(6) Stick, R.V., Stubbs, K.A. The synthesis of a new class of potential inhibitor for glycoside hydrolases. Journal of Carbohydrate Chemistry, 2005, 24, 529.

(5) Stick, R.V., Stubbs, K.A. From glycoside hydrolases to thioglycoligases: the synthesis of thioglycosides. Tetrahedron:Asymmetry, 2005, 16, 321.

(4) Stick, R.V., Stubbs, K.A., Watts, A.G. Modifying the regioselectivity of glycosynthase reactions through the rational design of modified acceptors. Australian Journal of Chemistry, 2004, 57, 779.

(3) Stick, R.V., Stubbs, K.A., Watts, A.G. The fluorination (at C5) of some derivatives of D-glucose. Australian Journal of Chemistry, 2004, 57, 345.

(2) Stick, R.V., Stubbs, K.A., Tilbrook, D.M.G., Watts, A.G. A new catalyst for the reductive elimination of acylated glycosyl bromides to form glycals. Australian Journal of Chemistry, 2002, 55, 83.

(1) Stick, R.V., Stubbs, K.A., Tilbrook, D.M.G. An improved synthesis of (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsinyl-beta-D-riboside, a common marine arsenical. Australian Journal of Chemistry, 2001, 54, 181.

Conference papers

(4) Vocadlo, D., Yuzwa, S., Shan, X., Cekic, N., Deng, L., Heinonen, J., Stubbs, K., Gloster, T., and Zhu, Y., Metabolic inhibitors of glycosyltransferases as tools for glycobiology. Glycobiology, 2013, 23, 1340.

(3) Gandy, M.N., Debowski, A.W., and Stubbs, K.A.* The development of tools for the affinity-based proteomic profiling of exo-alpha-glycosidase activity. Glycobiology, 2011, 21, 1517.

(2) Vocadlo, D., Yuzwa, S., Macauley, M.S., Henioen, J.E., Shan, X., Whitworth, G.E., Stubbs, K.A., Davies, G.J., Dennis, R., Modulators of intracellular glycosylation limit microtubule-associated protein tau phosphorylation in vivo. Biochemistry and Cell Biology-Biochimie et Biologie Cellulaire, 2010, 88, 412.

(1) Whitworth, G.E., Stubbs, K.A., Macauley, M.S., Dennis, R.J., Davies, G.J., Greig, I.R., and Vocadlo, D.J. Analysis of PUGNAc and NAG-thiazoline as Transition State Analogues for Human O-GlcNAcase: Mechanistic and Structural Insights into Inhibitor Selectivity and Transition State Poise. Biochemistry and Cell Biology-Biochimie et Biologie Cellulaire, 2008, 86, 201.

News and Views

(1) Coombe, D., Davis, C., Fincher, G., McConville, M., Packer, N., Stubbs, K.A., Williams, S., and Dell, A., Letter to the Glycoforum: Transforming Glycoscience: An Australian Perspective. Glycobiology, 2014, 24, 1-3.
Roles, responsibilities and expertise
2017-present - Member of School of Molecular Sciences Research Commitee
2015-Present - Editorial Advisory Board, Organic & Biomolecular Chemistry, Royal Society of Chemistry
Funding received
ARC Future Fellowship
ARC Discovery Grants
National Health and Medical Research Council Project Grants
Cancer Council WA
WA Medical and Health and Research Infrastructure Funds
Perpetual Funding
UWA Research Development Award
UWA Research Collaboration Awards
Bayer CropScience
Royal Australian Chemistry Institute
Royal Society of Chemistry
Australian Society of Biochemistry and Molecular Biology
Canadian Society of Biochemistry, Molecular and Cellular Biology
Society for Glycobiology
Honours and awards
2015 University of Western Australia Vice-Chancellor’s Mid-Career Research Award

2013 Royal Australian Chemical Institute Athel Beckwith Lectureship

2012 Royal Australian Chemical Institute Rennie Memorial Medalist

2012 Finalist in the Scopus Young Researcher Award (Life and Biological Sciences)

2011 Australian Institute of Policy and Science Young Tall Poppy for Western Australia

2011 Hoffmann-La Roche/Groupe Français des Glucides Travel Award

2008-2010 Michael Smith Foundation of Health Research Post-Doctoral Fellowship - Awarded to one of the best applicants in the Biomedical Sciences Section.

2007 Merck Frosst Biology Research Day Presentation Award - For the best presentation at Merck Frosst Biology Research Day

2007 Canadian Society of Biochemistry, Molecular and Cellular Biology - Awarded for being the best Post-Doctoral Fellow at the CSBMCB Symposium Meeting, 2007.

2007 Merck Frosst Travel Award – Awarded to give talks at universities in the eastern provinces of Canada.

2004 Australia New Zealand Glycoscience Group Travel Award - Awarded to attend the International Carbohydrate Symposium, Glasgow, Scotland.
Vocadlo, D., McEachern, E., Whitworth, G., Macauley, M., Heinonen, J., Stubbs, K., Li, T.-S., ‘Selective glycosidase inhibitors and uses thereof’, WO2008025170.
Vocadlo, D.J, McEachern, E.J, Stubbs, K., ‘Selective glycosidase inhibitors and uses thereof’, WO2010012106.
Vocadlo, D.J, McEachern, E.J, Stubbs, K., ‘Selective glycosidase inhibitors and uses thereof’, US20120095033.
Vocadlo, D., McEachern, E., Stubbs, K., Li, T.-S., Whitworth, G., Heinonen, J., Macauley, M., ‘Selective glycosidase inhibitors and uses thereof’, US20120316207.
Chemistry Program Honours Coordinator
CHEM1002 Chemistry-Structure and Reactivity
CHEM3004 Synthetic Applications
Useful links
Twitter: @kaschembio
Current projects
PhD & Honours Research Opportunities:





Prof. David Vocadlo, Simon Fraser University
Prof. Gideon Davies, University of York
Dr. Brian Mark, University of Manitoba
Dr. Alisdair Boraston, University of Victoria
Dr. Joshua Mylne, Univeristy of Western Australia
Prof. Colin Raston, Flinders University
Dr Sean Sweeney, University of York
Prof. Barry Marshall, Univeristy of Western Australia
A/Prof. Mohammed Benghezal, Univeristy of Western Australia
Prof. Alice Vrielink, Univeristy of Western Australia
A/Prof. Charlene Kahler, University of Western Australia

Research profile
Research profile and publications

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Last updated:
Tuesday, 3 November, 2015 2:39 PM