Rutledge, Peter - University of Sydney

研究领域

Hydrocarbon Oxidation and C-H Activation: The conversion of simple hydrocarbons (alkanes, alkenes and aromatic compounds) to functionalised targets is of great interest in synthetic and medicinal chemistry, but many of these key transformations are inaccessible with current synthetic methods. Nature uses highly efficient enzyme systems to oxidise hydrocarbons in high yield with complete selectivity. We are working to develop new catalysts inspired by these biological systems, and to use them for the selective oxidation of hydrocarbon substrates: new reagents for synthesis and for the environment. We have synthesised a series of small-molecule systems that mimic the non-heme iron oxidase (NHIO) active site and are developing these as catalysts for biomimetic hydrocarbon oxidation and iron-mediated C-H activation. Antibiotics Chemistry: The rise and rise of the so-called 'Superbugs' is well documented in the media. Bacteria that are resistant to (i.e. not killed by) most current antibiotics are increasingly widespread, and the need for new drugs and new strategies to combat them grows ever more important. We are widely interested in antibiotics chemistry and antibiotic biosynthesis, and are pursuing a number of approaches to meet the challenges posed by antibiotic resistant bacteria. Current strategies include the synthesis of new cyclobutanone antibiotics and the design of antibiotics with novel 'double-punch' and 'resistance-activated' modes of action. Mercury Binding: Heavy metals like cadmium and mercury form some of the most toxic materials known. Yet some plants and microbes have developed strategies to live in locales prone to high levels of cadmium and mercury pollution, using sulfur-rich proteins to bind and the toxic metal ions and sequester them away from the rest of the cell's machinery. These proteins incorporate high numbers of cysteine residues, which makes them effective agents for heavy metal sequestration: the numerous sulfur atoms bind tightly to mercury, cadmium and other metal ions. Our approach uses thiol- and sulfide-rich peptides as agents for binding and sensing mercury. Nitrile Hydratase Mimics and Mechanism: Nitrile hydratase is an unusual metalloenzyme that brings about the selective conversion of nitriles to primary amides. Crystal structures of nitrile hydratases show a remarkable ligand environment in the active site. Two nitrogen atoms from main-chain amides bind to the metal (iron(III) or cobalt(III)), along with three sulfur atoms, each in a different oxidation state. And these five metal binding ligands are located in a short section of the primary sequence, spread across only six amino acids in one peptide chain. We are working to develop new peptide-based systems as bio-inspired catalysts for nitrile hydration, to study the unusual sulfur oxidation that occurs at the nitrile hydratase active site, and to elucidate a detailed mechanism for nitrile hydratase catalysis.

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Yu, M., Nagalingam, G., Ellis, S., Martinez, E., Sintchenko, V., Spain, M., Rutledge, P., Todd, M., Triccas, J. (2016). Nontoxic metal-cyclam complexes, a new class of compounds with potency against drug-resistant Mycobacterium tuberculosis. Journal of Medicinal Chemistry, 59(12), 5917-5921. [More Information] Wong, J., Ast, S., Yu, M., Flehr, R., Counsell, A., Turner, P., Crisologo, P., Todd, M., Rutledge, P. (2016). Synthesis and evaluation of 1,8-disubstituted-cyclam/naphthalimide conjugates as probes for metal ions. ChemistryOpen, 5(4), 375-385. [More Information] Canning, J., Ast, S., Hossain, M., Chan, H., Rutledge, P., Jamalipour, A. (2015). Bend and twist intramolecular charge transfer and emission for selective metal ion sensing. Optical Materials Express, 5(11), 2675-2681. [More Information] Hossain, M., Canning, J., Ast, S., Cook, K., Rutledge, P., Jamalipour, A. (2015). Combined "dual" absorption and fluorescence smartphone spectrometers. Optics Letters, 40(8), 1737-1740. [More Information] Rutledge, P., Challis, G. (2015). Discovery of microbial natural products by activation of silent biosynthetic gene clusters. Nature Reviews Microbiology, 13(8), 509-523. [More Information] Hossain, M., Canning, J., Ast, S., Rutledge, P., Jamalipour, A. (2015). Early Warning Smartphone Diagnostics for Water Security and Analysis Using Real-Time pH Mapping. Photonic Sensors, 5(4), 289-297. [More Information] Yu, M., Wong, J., Tang, C., Turner, P., Todd, M., Rutledge, P. (2015). Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Bronsted acids. Beilstein Journal of Organic Chemistry, 11, 37-41. [More Information] Porter, D., Poon, B., Rutledge, P. (2015). Iron complexes of tetramine ligands catalyse allylic hydroxy-amination via a nitroso-ene mechanism. Beilstein Journal of Organic Chemistry, 11, 2549-2556. [More Information] Hossain, M., Canning, J., Ast, S., Rutledge, P., Yen, T., Jamalipour, A. (2015). Lab-in-a-phone: Smartphone-based portable fluorometer for pH measurements of environmental water. IEEE Sensors Journal, 15(9), 5095-5102. [More Information] Devi, P., Barry, S., Houlihan, K., Murphy, M., Turner, P., Jensen, P., Rutledge, P. (2015). Synthesis and structural characterisation of amides from picolinic acid and pyridine-2,6-dicarboxylic acid. Scientific Reports, 9, 1-6. [More Information] Ast, S., Kuke, S., Rutledge, P., Todd, M. (2015). Using click chemistry to tune the properties and the fluorescence response mechanism of structurally similar probes for metal ions. European Journal of Inorganic Chemistry, 2015 (1), 58-66. [More Information] Byrne, C., Houlihan, K., Devi, P., Jensen, P., Rutledge, P. (2014). Bio-inspired nitrile hydration by peptidic ligands based on L-cysteine, L-methionine or L-penicillamine and pyridine-2,6-dicarboxylic acid. Molecules, 19(12), 20751-20767. [More Information] Yu, M., Ast, S., Yu, Q., Lo, A., Flehr, R., Todd, M., Rutledge, P. (2014). Incorporating a piperidinyl group in the fluorophore extends the fluorescence lifetime of click-derived cyclam-naphthalimide conjugates. PloS One, 9(7), 1-12. [More Information] Yu, M., Ryan, T., Ellis, S., Bush, A., Triccas, J., Rutledge, P., Todd, M. (2014). Neuroprotective peptide-macrocycle conjugates reveal complex structure-activity relationships in their interactions with amyloid beta. Metallomics, 6(10), 1931-1940. [More Information] Ast, S., Rutledge, P., Todd, M. (2014). pH-Responsive quantum dots (RQDs) that combine a fluorescent nanoparticle with a pH-sensitive dye. Physical Chemistry Chemical Physics, 16(46), 25255-25257. [More Information] Ast, S., Rutledge, P., Todd, M. (2014). The properties and performance of a pH-responsive functionalised nanoparticle. Faraday Discussions, 175, 171-187. [More Information] Yu, M., Yu, Q., Rutledge, P., Todd, M. (2013). A fluorescent "allosteric scorpionand" complex visualizes a biological recognition event. ChemBioChem: a European journal of chemical biology, 14(2), 224-229. [More Information] Yu, M., Lim, N., Ellis, S., Nagase, H., Triccas, J., Rutledge, P., Todd, M. (2013). Incorporation of bulky and cationic cyclam-triazole moieties into marimastat can generate potent MMP inhibitory activity without inducing cytotoxicity. ChemistryOpen, 2(3), 99-105. [More Information] Dungan, V., Poon, B., Barrett, E., Rutledge, P. (2013). L-Proline derived mimics of the non-haem iron active site catalyse allylic oxidation in acetonitrile solutions. Tetrahedron Letters, 54(10), 1236-1238. [More Information] Cheung, S., McCarl, V., Holmes, A., Coleman, N., Rutledge, P. (2013). Substrate range and enantioselectivity of epoxidation reactions mediated by the ethene-oxidising Mycobacterium strain NBB4. Applied Microbiology and Biotechnology, 97(3), 1131-1140. [More Information]