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Professor Katrina A Jolliffe


Contact Details

Professor of Chemistry and Head of School
Room 515
School of Chemistry, Building F11
The University of Sydney, NSW, 2006, Australia
E: kate.jolliffe@sydney.edu.au
T: +61-2-9351-2297
F: +61-2-9351-3329

Career Profile

  • BSc(Hons), University of New South Wales, 1993
  • PhD, University of New South Wales, 1997
  • Postdoctoral Fellow, Universiteit Twente, The Netherlands 1996-1998
  • Temporary Lecturer, University of Nottingham, UK, 1998-2000
  • Research Fellow, Australian National University, 2000-2002
  • QEII Fellow, University of Sydney, 2002- 2007
  • Senior Lecturer, University of Sydney, 2007
  • Associate Professor, University of Sydney, 2008
  • Professor, University of Sydney, 2009 -

Recent Achievements

  • 2012: Elected a Fellow of the Royal Society of Chemistry
  • 2007: NSW and ACT Young Tall Poppy Science award
  • 2006: Biota award for Medicinal Chemistry
  • 2004: RACI Organic Division Lectureship for Recently Appointed Staff

Areas of Interest

  • Synthetic organic chemistry
  • Cyclic Peptide Synthesis
  • Molecular recognition and Sensing
  • Molecular self-assembly
  • Design and synthesis of new antifungal agents

Details of Research

Synthesis of Natural and Novel Cyclic Peptides

Naturally occurring cyclic peptides exhibit a wide range of biological activities and are often more resistant to enzymatic hydrolysis than their linear counterparts. Additionally, the restricted conformational flexibility of cyclic peptides allows them to present functional groups in a spatially well-defined manner and this is of use in the study and mimicry of protein folding and in the determination of the active conformations of peptides. However, the head-to-tail cyclisation of linear peptides is often a slow and low-yielding reaction. We have developed a new method for the efficient head-to-tail synthesis of small cyclic peptides and examined its use in a number of model systems. Our methodology has been employed in the synthesis of the naturally occurring cyclic peptides mahafacyclin B and axinellin A and we are currently investigating the scope of our cyclisation method and its application in the synthesis of both naturally occurring and novel cyclic peptides.

Rigidified Cyclic Peptides as Supramolecular Scaffolds

The introduction of aromatic subunits into a cyclic peptide backbone greatly reduces the conformational flexibility of these already constrained molecules and allows functional groups to be arranged in a convergent and preorganised manner suitable for binding of a guest molecule. We have used analogues of the naturally occurring Lissoclinum family of cyclic peptides, which incorporate oxazole subunits in the macrocyclic ring, to provide rigid scaffolds for the positioning of molecular receptor groups. These cyclic peptides are further rigidified by the presence of a network of bifurcated hydrogen bonds and their synthesis from amino acid building blocks allows a wide range of functional groups to be appended to the scaffold. Compounds bearing dipicolylamino zinc(II) complexes have been used to bind biologically relevant anions (e.g. pyrophosphate ions) in aqueous solution with high affinity and good selectivity. We are currently investigating how the selectivity of these receptors for target anions can be improved and looking at the attachment of alternative binding sites to the cyclic peptide scaffolds .

Development of New Antifungal Drugs

Invasive fungal infections are a serious and escalating health issue, especially in immuno-compromised hosts. Current drugs are limited in safety and/or efficacy and resistant fungi are an emerging problem. New antifungal drugs with novel modes of action are urgently needed. In collaboration with Prof. Tania Sorrell and coworkers (USyd, Westmead), we have designed and synthesised several classes of new antifungal agents. These compounds are showing great promise as antifungal drugs, with the best compounds having activity comparable to that of the current ‘gold standard’ for antifungal therapy, Amphotericin B. Current research is focussed on determining the mode of action of these compounds, which in two of the compound classes may be related to inhibition of the fungal virulence factor, phospholipase B, and in further developing classes of compounds with broad spectrum antifungal activity.

Molecular Self-Assembly

The design of molecules capable of self-assembly to form novel multicomponent supramolecular structures remains a significant challenge for synthetic chemists. Despite intense interest in the field, the assembly of synthetic structures which replicate the complexity and control apparent in the larger self-assembled biological structures is yet to be achieved. An understanding of the interactions between molecules is required to enable molecular building blocks capable of forming such structures to be designed. We are investigating the self-assembly of molecular aggregates (e.g. capsules) using both hydrogen bonding and metal-ligand interactions as the glue to hold our molecular subunits together.

Publications (2009 to 2013)

  1. Chapman, R; Koh, ML; Warr, GG; Jolliffe, KA and Perrier, S. Structure elucidation and control of cyclic peptide-derived nanotube assemblies in solution. Chemical Science, 4 (6), 2581-2589, 2013. DOI: 10.1039/c3sc00064h

  2. Yuen, KY and Jolliffe, KA. Bis[zinc(II)dipicolylamino]-functionalised peptides as high affinity receptors for pyrophosphate ions in water. Chemical Communications, 49 (42), 4824-4826, 2013. DOI: 10.1039/c3cc40937f

  3. Collin, F; Thompson, RE; Jolliffe, KA; Payne, RJ and Maxwell, A. Fragments of the bacterial toxin microcin B17 as gyrase poisons. PLOS|ONE, 8 (4), e61459, 2013. DOI: 10.1371/journal.pone.0061459

  4. Liu, X; Ngo, HT; Ge, Z; Butler, SJ and Jolliffe, KA. Tuning colourimetric indicator displacement assays for naked-eye sensing of pyrophosphate in aqueous media. Chemical Science, 4 (4), 1680-1686, 2013. DOI: 10.1039/c3sc22233k

  5. Chapman, R; Jolliffe, KA and Perrier, S. Multi-shell soft nanotubes from cyclic peptide templates. Advanced Materials, 25 (8), 1170-1172, 2013. DOI: 10.1002/adma.201204094

  6. Sheridan, EJ; Austin, CJD; Aitken, JB; Vogt, S; Jolliffe, KA; Harris, HH and Rendina, LM. Synchrotron X-ray fluorescence studies of a bromine-labelled cyclic RGD peptide interacting with individual tumor cells. Journal of Synchrotron Radiation, 20 (2), 226-233, 2013. DOI: 10.1107/S0909049513001647

  7. Chapman, R; Warr, GG; Perrier, S and Jolliffe, KA. Water-soluble and pH-responsive polymeric nanotubes from cyclic peptide templates. Chemistry: A European Journal, 19 (6), 1955-1961, 2013. DOI: 10.1002/chem.201203602

  8. Dungan, VJ; Ngo, HT; Young, PG and Jolliffe, KA. High affinity sulfate binding in aqueous media by cyclic peptides with thiourea arms. Chemical Communications, 49 (3), 264-266, 2013. DOI: 10.1039/c2cc37686e

  9. Lee, M; Zali-Boeini, H; Li, F; Lindoy, LF and Jolliffe, KA. Synthesis of tris-(azacrown) ethers for carboxylic acid recognition. Tetrahedron, 69 (1), 38-42, 2013. DOI: 10.1016/j.tet.2012.10.067

  10. Butler, SJ and Jolliffe, KA. Selective pyrophosphate recognition by cyclic peptide receptors in physiological saline. Chemistry - An Asian Journal, 7 (11), 2621-2628, 2012. DOI: 10.1002/asia.201200627

  11. Thompson, RE; Payne, RJ and Jolliffe, KA. Total synthesis of cyclocitropside A and its conversion to cyclocitropsides B and C via asparagine deamidation. Organic Letters, 14 (19), 5110-5113, 2012. DOI: 10.1021/ol3023853

  12. Cochrane, JR; Yoon, DH; McErlean, CSP and Jolliffee, KA. A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues. Beilstein Journal of Organic Chemistry, (8), 1344-1351, 2012. DOI: 10.3762/bjoc.8.154

  13. Chapman, R; Danial, M; Koh, ML; Jolliffe, KA and Perrier, S. Design and properties of functional nanotubes from the self-assembly of cyclic peptide templates. Chemical Society Reviews, 41 (18), 6023-6041, 2012. DOI: 10.1039/c2cs35172b

  14. Heine, KB; Fairweather, KA; Heine, A; Clegg, JK; Jolliffe, KA; Gloe, K; Gloe, K; Bernhard, G and Henle, T. Unusual absence of head-to-tail chains in the crystal structure of glycyl-L-glutamyl-L-phosphoseryl-L-leucine. Journal of Chemical Crystallography, 42 (8), 839-845, 2012. DOI: 10.1007/s10870-012-0322-9

  15. Dong, Y; Loong, DTJ; Yuen, AKL; Black, RJ; O'Malley, S; Clegg, JK; Lindoy, LF and Jolliffe, KA. Molecular capsules and coordination polymers from a backbone-modified cyclic peptide bearing pyridyl arms. Supramolecular Chemistry, 24 (7), 508-519, 2012. DOI: 10.1080/10610278.2012.688128

  16. Jolliffe, KA. Pseudoprolines: Effective tools for the cyclisation of small peptides. Journal of Peptide Science, 18, Supplement 1, S31-S31, 2012. DOI: 10.1002/psc.2448

  17. Ngo, HT; Liu, X and Jolliffe, KA. Anion recognition and sensing with Zn(II)-dipicolylamine complexes. Chemical Society Reviews, 41 (14), 4928-4965, 2012. DOI: 10.1039/c2cs35087d

  18. Poon, CK; Chapman, R; Jolliffe, KA and Perrier, S. Pushing the limits of copper mediated azide-alkyne cycloaddition (CuAAC) to conjugate polymeric chains to cyclic peptides. Polymer Chemistry, 3 (7), 1820-1826, 2012. DOI: 10.1039/c2py00510g

  19. Young, PG; Clegg, JK and Jolliffe, KA. Neutral cryptand-like cyclic peptide-thiourea receptors for selective recognition of sulphate anions in aqueous solvents. Supramolecular Chemistry, 24 (2), 77-87, 2012. DOI: 10.1080/10610278.2011.622388

  20. Young, PG and Jolliffe, KA. Selective recognition of sulfate ions by tripodal cyclic peptides functionalised with (thio)urea binding sties. Organic & Biomolecular Chemistry, 10 (13), 2664-2672, 2012. DOI: 10.1039/c2ob06964d

  21. Davis, MR; Singh, EK; Wahyudi, H; Alexander, LD; Kunicki, JB; Nazarova, LA; Fairweather, KA; Giltrap, AM; Jolliffe, KA and McAlpine, SR. Synthesis of sansalvamide A peptidomimetics: triazole, oxazole, theazole, and pseudoproline containing compounds. Tetrahedron, 68 (4), 1029-1051, 2012. DOI: 10.1016/j.tet.2011.11.089

  22. Clegg, JK; Antonioli, B; Bray, DJ; Gloe, K; Gloe, K; Jolliffe, KA; Kataeva, ON; Meehan, GV and Wenzel, M. Liquid-liquid extraction studies with 4,4´-biphenylene-spaced bis-β-diketones. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 71 (3-4), 319-329, 2011. DOI: 10.1007/s10847-011-9954-1

  23. Zuo, X; Djordjevic, JT; Oei, JB; Desmarini, D; Schibeci, SD; Jolliffe, KA and Sorrell, TC. Miltefosine induces apoptosis-like cell death in yeast via Cox9p in cytochrome c oxidase. Molecular Pharmacology, 80 (3), 476-485, 2011. DOI: 10.1124/mol.111.072322

  24. Chapman, R; Jolliffe, KA and Perrier, S. Modular design for the controlled production of polymeric nanotubes from polymer/peptide conguates. Polymer Chemistry, 2 (9), 1956-1963, 2011. DOI: 10.1039/c1py00202c

  25. Shamsi, F; Coster, H and Jolliffe, KA. Characterization of peptide immobilization on an acetylene terminated surface via click chemistry. Surface Science, 605 (19-20), 1763-1770, 2011. DOI: 10.1016/j.susc.2011.05.027

  26. Dudek, M; Clegg, JK; Glasson, CRK; Kelly, N; Gloe, K; Gloe, K; Kelling, A; Buschmann, H-J; Jolliffe, KA; Lindoy, LF and Meehan, GV. Interaction of copper(II) with ditopic pyridyl-beta-diketone ligands: Dimeric, framework, and metallogel structures. Crystal Growth & Design, 11 (5), 1697-1704, 2011. DOI: 10.1021/cg101629w

  27. Clegg, JK; Li, F; Jolliffe, KA; Meehan, GV and Lindoy, LF. An expanded neutral M4L6 cage that encapsulates four tetrahydrofuran molecules. Chemical Communications, 47 (21), 6042-6044, 2011. DOI: 10.1039/c1cc11167a

  28. Dehn, S; Chapman, R; Jolliffe, KA and Perrier, S. Synthetic strategies for the design of peptide/polymer conjugates. Polymer Reviews, 51 (2), 214-234, 2011. DOI: 10.1080/15583724.2011.566404

  29. Butler, SJ and Jolliffe, KA. Synthesis of a family of cyclic peptide-based anion receptors. Organic & Biomolecular Chemistry, 9 (9), 3471-3483, 2011. DOI: 10.1039/c0ob01072c

  30. Kakwere, H; Payne, RJ; Jolliffe, KA and Perrier, S. Self-assembling macromolecular chimeras: Controlling fibrillization of a beta-sheet forming peptide by polymer conjugation. Soft Matter, 7 (8), 3754-3757, 2011. DOI: 10.1039/c0sm01237h

  31. Götzke, L; Gloe, K; Jolliffe, KA; Lindoy, LF; Heine, A; Doert, T; Jäger, A and Gloe, K. Nickel(II) and zinc(II) complexes of , N-substituted di(2-picolyl)amine derivatives: Synthetic and structural studies. Polyhedron, 30 (5), 708-714, 2011. DOI: 10.1016/j.poly.2010.12.005

  32. Shamsi, F; Coster, H; Jolliffe, KA and Chilcott, T. Characterization of the substructure and properties of immobilized peptides on silicon surface. Materials Chemistry and Physics, 126 (3), 955-961, 2011. DOI: 10.1016/j.matchemphys.2010.11.058

  33. Hunter, L; Jolliffe, KA; Jordan, MJT; Jensen, P and Macquart, RB. Synthesis and conformational analysis of α,β-difluoro-γ-amino acid derivatives. Chemistry: A European Journal, 17 (8), 2340-2343, 2011. DOI: 10.1002/chem.201003320

  34. Thompson, RE; Jolliffe, KA and Payne, RJ. Total synthesis of microcin B17 via a fragment condensation approach. Organic Letters, 13 (4), 680-683, 2011. DOI: 10.1021/ol102916b

  35. Butler, SJ; Jolliffe, KA; Lee, WYG; McDonough, MJ and Reynolds, AJ. Synthesis of backbone modified cyclic peptides bearing dipicolylamino sidearms. Tetrahedron, 67 (5), 1019-1029, 2011. DOI: 10.1016/j.tet.2010.11.100

  36. Young, PG; Clegg, JK; Bhadbhade, M and Jolliffe, KA. Hybrid cyclic peptide-thiourea cryptands for anion recognition. Chem. Commun., 47 (1), 463-465, 2011. DOI: 10.1039/c0cc02223c

  37. Chapman, R; Jolliffe, KA and Perrier, S. Synthesis of self-assembling cyclic peptide-polymer conjugates using click chemistry. Australian Journal of Chemistry, 63 (8), 1169-1172, 2010. DOI: 10.1071/CH10128

  38. Conroy, T; Jolliffe, KA and Payne, RJ. Synthesis of N-linked glycopeptides via solid-phase aspartylation. Organic & Biomolecular Chemistry, 8 (16), 3723-3733, 2010. 10.1039/c003673k

  39. Cochrane, JR; McErlean, CSP and Jolliffe, KA. Total synthesis and assignment of the side chain stereochemistry of LI-F04a: An antimicrobial cyclic depsipeptide. Organic Letters, 12 (15), 3394-3397, 2010. DOI: 10.1021/ol101254m

  40. Chen, SC-A; Biswas, C; Bartley, R; Widmer, F; Pantarat, N; Obando, D; Djordjevic, JT; Ellis, DH; Jolliffe, KA and Sorrell, TC. In vitro antifungal activities of bis(alkylpyridinium)alkane compounds against pathogenic yeasts and molds. Antimicrobial Agents and Chemotherapy, 54 (8), 3233-3240, 2010. DOI: 10.1128/AAC.00231-10

  41. Fairweather, KA; Sayyadi, N; Luck, IJ; Clegg, JK and Jolliffe, KA. Synthesis of all-L cyclic tetrapeptides using pseudoprolines as removable turn inducers. Organic Letters, 12 (14), 3136-3139, 2010. DOI: 10.1021/ol101018w

  42. Wong, MSY and Jolliffe, KA. Synthesis of cyclogossine B using a traceless pseudoproline turn-inducer. Aust. J. Chem., 63 (5), 797-801, 2010. DOI: 10.1071/CH09643

  43. Kakwere, H; Chun, CKY; Jolliffe, KA; Payne, RJ and Perrier, S. Polymer-peptide chimeras for the multivalent display of immunogenic peptides. ChemComm., 46 (13), 2188-2190, 2010. DOI: 10.1039/b924112d

  44. Meng, Q; Clegg, JK; Jolliffe, KA; Lindoy, LF; Lan, M and Wei, G. A new nickel(II) coordination polymer derived from [Ni(N,N-ethylenebis(1,1,1-trifluoroacetylacetoneiminato)} and 1,4-diazabicyclo[2.2.2]octane. Inorganic Chemistry Communications, 13 (4), 558-562, 2010. DOI: 10.1016/j.inoche.2010.02.004

  45. Clegg, JK; Hayter, MJ; Jolliffe, KA; Lindoy, LF; McMurtrie, JC; Meehan, GV; Neville, SM; Parsons, S; Tasker, PA; Turner, P and White, FJ. New discrete and polymeric supramolecular architectures derived from dinuclear Co(II), Ni(II) and Cu(II) complexes of aryl-linked bis-beta-diketonato ligands and nitrogen bases: Synthetic, structural and high pressure studies. Dalton Transactions, 39 (11), 2804-2815, 2010. DOI: 10.1039/b920199h

  46. Black, RJG; Dungan, VJ; Li, RYT; Young, PG and Jolliffe, KA. A cyclooligomerisation approach to backbone-modified cyclic peptides bearing guanidinium arms. Synlett, (4), 551-554, 2010. DOI: 10.1055/s-0029-1219155

  47. Clegg, JK; Iremonger, SS; Hayter, MJ; Southon, PD; Macquart, RB; Duriska, MB; Jensen, P; Turner, P; Jolliffe, KA; Kepert, CJ; Meehan, GV and Lindoy, LF. Hierarchical self-assembly of a chiral metal-organic framework displaying pronounced porosity. Angew. Chem. Int. Ed., 49 (6), 1075-1078, 2010. DOI: 10.1002/anie.200905497

  48. Fairweather, KA; Sayyadi, N; Roussakis, C and Jolliffe, KA. Synthesis of the cyclic heptapeptide axinellin A. Tetrahedron, 66 (4), 935-939, 2010. DOI: 10.1016/j.tet.2009.11.090

  49. Antonioli, B; Büchner, B; Clegg, JK; Gloe, K; Gloe, K; Götzke, L; Heine, A; Jäger, A; Jolliffe, KA; Kataeva; O; Kataev; V; Klingeler, R; Krause, T; Lindoy, LF; Popa, A; Seichter, W and Wenzel, M. Interaction of an extended series of N-substituted di(2-picolyl)amine derivatives with copper(II). Synthetic, structural, magnetic, and solution studies. Dalton Transactions, (24), 4795-4805, 2009. DOI: 10.1039/b901832h

  50. Garner, J; Jolliffe, KA; Harding, MM and Payne, RJ. Synthesis of homogeneous antifreeze glycopeptides via a ligation-desulfurisation strategy. Chem. Commun., (45), 6925-6927, 2009. DOI: 10.1039/b918021d

  51. Obando, D; Pantarat, N; Handke, R; Koda, Y; Widmer, F; Djordjevic, JT; Ellis, DH; Sorrell, TC and Jolliffe, KA. Synthesis, antifungal, haemolytic and cytotoxic activities of a series of bis(alkylpyridinium)alkanes. Bioorganic & Medicinal Chemistry, 17 (17), 6329-6339, 2009. DOI: 10.1016/j.bmc.2009.07.037

  52. Clegg, JK; Cochrane, JR; Sayyadi, N; Skropeta, D; Turner, P and Jolliffe, KA. Solid-state and solution-phase conformations of pseudoproline-containing dipeptides. Australian Journal of Chemistry, 62 (7), 711-719, 2009. DOI: 10.1071/CH09151

  53. Conroy, T; Jolliffe, KA and Payne, RJ. Efficient use of the Dmab protecting group: applications for the solid-phase synthesis of N-linked glycopeptides. Organic & Biomolecular Chemistry, 7 (11), 2255-2258, 2009. DOI: 10.1039/b821051a

  54. Carolan, JV; Butler, SJ and Jolliffe, KA. Selective anion binding in water with use of a zinc(II) dipicolylamino functionalized diketopiperazine scaffold. Journal of Organic Chemistry, 74 (8), 2992-2996, 2009. DOI: 10.1021/jo802555u