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associate Professor Richard J Payne


Contact Details

Associate Professor and Second Year Coordinator
Room 545
School of Chemistry, Building F11
The University of Sydney, NSW, 2006, Australia
E: richard.payne@sydney.edu.au
T: +61-2-9351-5877
F: +61-2-9351-3329
W: http://sydney.edu.au/science/chemistry/~payne

Career Profile

  • BSc (Hons, First Class) University of Canterbury, Christchurch, New Zealand. (1998-2001)
  • Research Associate, University of Canterbury, Christchurch, New Zealand. (2001-2002)
  • PhD (Gates Scholar), University of Cambridge (Downing College), Cambridge, UK. (2003-2006)
  • Postdoctoral Research Associate, University of Cambridge, Cambridge, UK. (2006)
  • Postdoctoral Research Associate (Lindemann Fellow), The Scripps Research Institute, La Jolla, California, USA. (2006-2008)
  • Royal Australian Chemical Institute Biota Medal for Medicinal Chemistry, 2008
  • Lecturer, The University of Sydney, (2008 - 2010)
  • Senior Lecturer, The University of Sydney (2011 - 2012)
  • Associate Professor, The University of Sydney (2013 - present).

Recent Achievements

  • 2010: New South Wales Young Tall Poppy Award
  • 2011: RACI's 2011 Rennie Memorial Medal
  • 2012: 2012 RACI Organic Chemistry Division Athel Beckwith lectureship.

Areas of Interest

Research in my group is focussed on utilising the tools of chemistry to address problems of biochemical and medicinal significance. Projects are multidisciplinary in nature, involving a combination of solution- and solid-phase organic synthesis, computer-aided drug discovery, compound screening technologies. Current projects include:

  • Rational design, synthesis and evaluation of new anti-infectives. More specifically, we are developing inhibitors that target novel pathways operating in pathogenic bacteria e.g. Mycobacterium tuberculosis (cause of TB) and parasitic organisms e.g. Plasmodium falciparum (cause of malaria).
  • Total synthesis of glycopeptides and glycoproteins of therapeutic interest.
  • Development of glycopeptide-based cancer vaccines.

For current research activities and opportunities please visit our home page: http://www.chem.usyd.edu.au/~payne

Publications (2009 - 2013)

  1. 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

  2. Tan, JHY; Ludeman, JP; Wedderburn, J; Canals, M; Hall, P; Butler, SJ; Taleski, D; Christopoulos, A; Hickey, MJ; Payne, RJ and Stone, MJ. Tyrosine sulfation of chemokine receptor CCR2 enhances interactions with both monomeric and dimeric forms of the chemokine monocyte chemoattractant protein-1 (MCP-1). Journal of Biological Chemistry, 288 (14), 10024-10034, 2013. DOI: 10.1074/jbc.M112.447359

  3. Malins, LR; Cergol, KM and Payne, RJ. Peptide ligation-desulfurization chemistry at arginine. ChemBioChem Communications, 14 (5), 559-563, 2013. DOI: 10.1002/cbic.201300049

  4. Payne, RJ. Total synthesis of erythropoietin through the development and exploitation of enabling synthetic technologies. Angewandte Chemie International Edition, 52 (2), 505-507, 2013. DOI: 10.1002/anie.201207906

  5. Wilkinson, BL; Day, S; Chapman, R; Perrier, S; Apostolopoulos, V and Payne, RJ. Synthesis and immunological evaluation of self-assembling and self-adjuvanting tricomponent glycopeptide cancer-vaccine candidates. Chemistry: A European Journal, 18 (51), 16540-16548, 2012. DOI: 10.1002/chem.201202629

  6. Bakmiwewa, SM; Fatokun, AA; Tran, A; Payne, RJ; Hunt, NH and Ball, HJ. Identification of selective inhibitors of indoleamine 2,3-dioxygenase 2. Bioorganic & Medicinal Chemistry Letters, 22 (24), 7641-7646, 2012. DOI: 10.1016/j.bmcl.2012.10.010

  7. Manos-Turvey, A; Cergol, KM; Salam, NK; Bulloch, EMM; Chi, G; Pang, A; Britton, WJ; West, NP; Baker, EN; Lott, JS and Payne, RJ. Synthesis and evaluation of M. tuberculosis salicylate synthase (MbtI) inhibitors designed to probe plasticity in the active site. Organic & Biomolecular Chemistry, 10 (46), 9223-9236, 2012. DOI: 10.1039/c2ob26736e

  8. 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

  9. Andrews, DU; Heazlewood, BR; Maccarone, AT; Conroy, T; Payne, RJ; Jordan, MJT and Kables, SH. Photo-tautomerization of acetaldehyde to vinyl alcohol: A potential route to tropospheric acids. Science, 337 (6099), 1203-1206, 2012. DOI: 10.1126/science.1220712

  10. Duncan, RC; Mohlin, F; Taleski, D; Coetzer, TH; Huntington, JA; Payne, RJ; Blom, AM; Pike, RN and Wijeyewickrema, LC. Identification of a catalytic exosite for complement component C4 on the serine protease domain of C1s. The Journal of Immunology, 189 (5), 2365-2373, 2012. DOI: 10.4049/jimmunol.1201085

  11. Maghzal, GJ; Cergol, K; Suarna, C; Newington, D; Kettle, AJ; Payne, RJ; Stocker, R, et al. In vivo detection of myeloperoxidase activity by LC/MS analysis of 2-chloro-ethidium, a novel product formed from the reaction of hydroethidine with hypochlorous acid and chloramines. Free Radical Biology and Medicine, 53 (1), s223-s224, 2012. DOI: 10.1016/j.freeradbiomed.2012.08.469

  12. Chi, G; Manos-Turvey, A; O'Connor, PD; Johnston, JM; Evans, GL; Baker, EN; Payne, RJ; Lott, JS and Bullock, EMM. Implications of binding mode and active site flexibility for inhibitor potency against the salicylate synthase from Mycobacterium tuberculosis. Biochemistry, 51 (24), 4868-4879, 2012. DOI: 10.1021/bi3002067

  13. Malins, LR and Payne, RJ. Synthesis and utility of β-selenol-phenylalanine for native chemical ligation − deselenization chemistry. Organic Letters, 14 (12), 3142-3145, 2012. DOI: 10.1021/ol3012265

  14. Tran, AT; West, NP; Britton, WJ and Payne, RJ. Elucidation of Mycobacterium tuberculosis type II dehydroquinase inhibitors using a fragment elaboration strategy. ChemMedChem, 7 (6), 1031-1043, 2012. DOI: 10.1002/cmdc.201100606

  15. Tan, JHY; Canals, M; Ludeman, JP; Wedderburn, J; Boston, C; Butler, SJ; Carrick, AM; Parody, TR; Taleski, D; Christopoulos, A; Payne, RJ and Stone, MJ. Design and receptor interactions of obligate dimeric mutant of chemokine monocyte chemattractant protein-1 (MCP-1). Journal of Biological Chemistry, 287 (18), 14692-14702, 2012. DOI: 10.1074/jbc.M111.334201

  16. Wilkinson, BL; Stone, RS; Capicciotti, CJ; Thaysen-Andersen, M; Matthews, JM; Packer, NH; Ben, RN and Payne, RJ. Total synthesis of homogeneous antifreeze glycopeptides and glycoproteins. Angewandte Chemie International Edition, 51 (15), 3606-3610, 2012. DOI: 10.1002/anie.201108682

  17. Hsieh, YSY; Wilkinson, B; O'Connell, MR; Mackay, JP; Matthews, JM and Payne, RJ. Synthesis of the bacteriocin glycopeptide sublancin 168 and S-glycosylated variants. Organic Letters, 14 (7), 1910-1913, 2012. DOI: 10.1021/ol300557g

  18. Graham, ME; Stone, RS; Robinson, PJ and Payne, RJ. Synthesis and protein binding studies of a peptide fragment of clathrin assembly protein AP180 bearing an O-linked beta-N-acetylglucosaminyl-6-phosphate modification. Organic & Biomolecular Chemistry, 10 (13), 2545-2551, 2012. DOI: 10.1039/c2ob07139h

  19. Hsieh, YSY; Taleski, D; Wilkinson, BL; Wijeyewickrema, LC; Adams, TE; Pike, RN and Payne, RJ. Effect of O-glycosylation and tyrosine sulfation of leech-derived peptides on binding and inhibitory activity against thrombin. Chemical Communications, 48 (10), 1547-1549, 2012. DOI: 10.1039/c1cc14773k

  20. Thaysen-Andersen, M; Wilkinson, BL; Payne, RJ and Packer, NH. Site-specific characterisation of densely O-glycosylated mucin-type peptides using electron transfer dissociation ESI-MS/MS. Electrophoresis, 32 (24), 3536-3545, 2011. DOI: 10.1002/elps.201100294

  21. Conroy, T; Guo, JT; Linington, RG; Hunt, NH and Payne, RJ. Total synthesis, stereochemical assignment, and antimalarial activity of gallinamide A. Chemistry: A European Journal, 17 (48), 13544-13552, 2011. DOI: 10.1002/chem.201102538

  22. Thomas, GL; Hsieh, YSY; Chun, CKY; Cai, Z-L; Reimers, JR and Payne, RJ. Peptide ligations accelerated by N-terminal aspartate and glutamate residues. Organic Letters, 13 (18), 4770-4773, 2011. DOI: 10.1021/ol2017356

  23. Taleski, D; Butler, SJ; Stone, MJ and Payne, RJ. Divergent and site-selective solid-phase synthesis of sulfopeptides. Chem. Asian J., 6 (6), 1316-1320, 2011.DOI: 10.1002/asia.201100232

  24. West, NP; Cergol, KM; Xue, M; Randall, EJ; Britton, WJ and Payne, RJ. Inhibitors of an essential mycobacterial cell wall lipase (Rv3802c) as tuberculosis drug leads. Chemical Communications, 47 (18), 5166-5168, 2011. DOI: 10.1039/c0cc05635a

  25. Wilkinson, BL; Chun, CKY and Payne, RJ. Synthesis of MUC1 glycopeptide thioesters and ligation via direct aminolysis. Peptide Science, 96 (2), 137-146, 2011. DOI: 10.1002/bip.21471

  26. 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

  27. Zhu, JZ; Millard, CJ; Ludeman, JP; Simpson, LS; Clayton, DJ; Payne, RJ; Widlanski, TS and Stone, MJ. Tyrosine sulfation influences the chemokine binding selectivity of peptides derived from chemokine receptor CCR3. Biochemistry, 50 (9), 1524-1534, 2011. DOI: 10.1021/bi101240v

  28. Chim, N; Habel, JE; Johnston, JM; Krieger, I; Miallau, L; Sankaranarayanan, R; Morse, RP; Bruning, J; Swanson, S; Kim, H; Kim, C-Y; Li, H; Bulloch, EM; Payne, RJ; Manos-Turvey, A; Hung, L-W; Baker, EN; Lott, JS; James, MNG; Terwilliger, TC; Eisenberg, DS; Sacchettini, JC and Goulding, CW. The TB structural genomics consortium: A decade of progress. Tuberculosis, 91 (2), 155-172, 2011. DOI: 10.1016/j.tube.2010.11.009

  29. Wilkinson, BL; Day, S; Malins, LR; Apostolopoulos, V and Payne, R. Self-adjuvanting multicomponent cancer vaccine candidates combining per-glycosylated MUC1 glycopeptides and the toll-like receptor 2 agonist Pam3CysSer. Angew. Chem. Int. Ed., 50 (7), 1635-1639, 2011. DOI: 10.1002/anie.201006115

  30. 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

  31. Tran, AT; Cergol, KM; West, NP; Randall, EJ; Britton, WJ; Bokkhari, SAI; Ibrahim, M; Lapthorn, AJ and Payne, RJ. Synthesis and evaluation of potent ene-yne inhibitors of type II dehydroquinases as tuberculois drug leads. ChemMedChem, 6 (2), 262-265, 2011. DOI: 10.1002/cmdc.201000399

  32. Conroy, T; Guo, JT; Hunt, NH and Payne, RJ. Total synthesis and antimalarial activity of symplostin 4. Organic Letters, 12 (23), 5576-5579, 2010. DOI: 10.1021/ol1024663

  33. Tran, AT; Cergol, KM; Britton, WJ; Bokhari, SAI; Ibrahim, M; Lapthorn, AJ and Payne, RJ. Rapid assembly of potent type II dehydroquinase inhibitors via “click” chemistry. Medicinal Chemistry Communcations, 1 (4), 271-275, 2010. DOI: 10.1039/c0md00097c

  34. Holt, DJ; Payne, RJ; Chow, WY and Abell, C. Fluorosurfactants for microdroplets: Interfacial tension analysis. Journal of Colloid and Interface Science, 350 (1), 205-211, 2010. DOI: 10.1016/j.jcis.2010.06.036

  35. Wilkinson, BL; Malins, LR; Chun, CKY and Payne, RJ. Synthesis of MUC1-lipopeptide chimeras. Chem. Commun., 46 (34), 6249-6251, 2010. DOI: 10.1039/c0cc01360a

  36. 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

  37. Payne, RJ; Bulloch, EMM; Kerbarh, O and Abell, C.Inhibition of chorismate-utilising enzymes by 2-amino-4-carboxypyridine and 4-carboxypyridone and 5-carboxypyridone analogues. Organic & Biomolecular Chemistry, 8 (15), 3534-3542, 2010. DOI: 10.1039/c004062b

  38. Manos-Turvey, A; Bulloch, EMM; Rutledge, PJ; Baker, EN; Lott, JS and Payne, RJ. Inhibition studies of Mycobacterium tuberculosis salicylate synthase (Mbtl). ChemMedChem, 5 (7), 1067-1079, 2010. DOI: 10.1002/cmdc.201000137

  39. 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

  40. Payne, RJ and Wong, C-H. Advances in chemical ligation strategies for the synthesis of glycopeptides and glycoproteins. Chem. Commun., 46 (1), 21-43, 2010. DOI: 10.1039/b913845e

  41. Thordarson, P and Payne, RJ. The inaugural Australian workshop on bioconjugate chemistry, UNSW 2008. Foreward in: Aust. J. Chem., 62 (10), 1318-1319, 2009. DOI: 10.1071/CH09412

  42. Chun, CKY and Payne, RJ. Synthesis of MUC1 peptide and glycopeptide dendrimers. Australian Journal of Chemistry, 62 (10), 1339-1343, 2009. (invited submission for feature edition on Bioconjugate Chemistry). DOI: 10.1071/CH09282

  43. 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

  44. Payne, RJ; Bulloch, EMM; Toscano, MM; Jones, MA; Kerbarh, O and Abell, C. Synthesis and evaluation of 2,5-dihydrochorismate analogues as inhibitors of the chorismate-utilising enzymes. Organic & Biomolecular Chemistry, 7 (11), 2421-2429, 2009. DOI: 10.1039/b901694e

  45. 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

  46. Thomas, GL and Payne, RJ. Phosphate-assisted ligation. Chem. Commun., (28), 4260-4262, 2009. DOI: 10.1039/b906492c Highlighted in meet our authors section: http://www.rsc.org/Publishing/Journals/cc/People/authors/Richard_Payne.asp