UC Spark

Professor James Morriss Coxon

Chemistry
Phone: +64 3 364 2987 ext. 6872
 Office: Rutherford 640

Fields of Research

  • Chemistry of steroids and terpenoids
  • Chemistry of strained ring systems
  • Molecular recognition including experimental and computational methodology
  • Organic photochemistry
  • Organic reaction mechanisms
  • Protein, polysaccharide and calpain inhibitor (cataract research) modelling

Researcher Summary

My research interest is in understanding organic reactions, particularly those of value in synthesis and or biochemistry. Many of our studies have involved the timing of molecular events and the difference in energy of competing processes including: strained small ring opening and molecular rearrangement, factors responsible for facial selection in cycloaddition reactions and - reactions at carbonyls, and the use of chiral templates in inducing selection. Other interests include molecular modelling studies (ab initio studies of strained ring rearrangements, carbohydrate solution properties, macrocyclic conformational problems and protein structure) and Cataract research (a joint project with Professor Andrew Abell and colleagues at Lincoln focuses in development of calpain inhibitors).

Subject Area: Disciplines

Future Research

  • Ab initio studies
  • Cataract research
  • Reaction chemistry
  • Molecular modelling

Key Methodologies

  • Ab initio calculations
  • Organic synthesis
  • Preparative chemistry
  • Reaction chemistry
  • Molecular modelling

Affiliations

Publications


  • Jiao, W.T., McDonald, Q., Coxon, J.M. and Parker, E.J. (2010) Molecular Modeling Studies of Peptide Inhibitors Highlight the Importance of Conformational Prearrangement for Inhibition of Calpain. Biochemistry 49(26): 5533-5539. http://dx.doi.org/10.1021/bi100048y. (Journal Article)
  • Jones, M.A., Coxon, J.M., McNabb, S.B., Mehrtens, J.M., Alexander, N.A., Jones, S., Chen, H., Buisan, C. and Abell, A.D. (2009) Efficient Large-Scale Synthesis of CAT811, A Potent Calpain Inhibitor of Interest in the Treatment of Cataract. Australian Journal of Chemistry 62(7): 671-675. http://dx.doi.org/10.1071/CH09101. (Journal Article)
  • Jones, S., Jones, M.A., McNabb, S.B., Aitken, S.G., Coxon, J.M. and Abell, A.D. (2009) N-heterocyclic dipeptide aldehyde calpain inhibitors. Protein and Peptide Letters 16(12): 1466-1472. (Journal Article)
  • Abell, A.D., Alexander, N.A., Aitken, S.G., Chen, H., Coxon, J.M., Jones, M.A., McNabb, S.B. and Muscroft-Taylor, A. (2009) Synthesis of macrocyclic β-strand templates by Ring Closing Metathesis. Journal of Organic Chemistry 74(11): 4354-4356. http://dx.doi.org/10.1021/jo802723w. (Journal Article)
  • Coxon, J.M. and Townsend, A.E. (2007) Computational study on the ring-opening reaction of protonated oxirane and methylpropene. Tetrahedron 63(25): 5665-5668. http://dx.doi.org/10.1016/j.tet.2007.03.168. (Journal Article)
  • Coxon, J.M., Townsend, M.A.E., Cambridge, J.R.A. and Nam, S.G.C. (2007) Epoxide Rearrangement (Invited). Heron Island, Australia: Heron Island Conference on Reactive Intermediates & Unusual Molecules, 7-14 Jul 2007. (Conference Contribution - Oral presentation)
  • Abell, A.D., Jones, M.A., Neffe, A.T., Aitken, S.G., Cain, T.P., Payne, R.J., McNabb, S.B., Coxon, J.M., Stuart, B.G., Pearson, D.S., Lee, H.Y-Y. and Morton, J.D. (2007) Investigation into the P3 Binding Domain of m-Calpain Using Photoswitchable Diazo- and Triazene-dipeptide Aldehydes: New Anticataract Agents. Journal of Medicinal Chemistry 50(12): 2916-2920. http://dx.doi.org/10.1021/jm061455n. (Journal Article)
  • Abell, A.D., Aitken, S.G., Coxon, J.M., Jones, M.A., Lee, H.Y.Y., McNabb, S.B., Morton, J.D., Neffe, A.T., Nikkel, J.M., Robertson, L.J.G. and Stuart, B.G. (2007) The Molecular Modelling of µ-Calpain and In-silico Design of Calpain Inhibitors. Adelaide, Australia: 22nd Royal Australian Chemical Institute Organic Conference (22RACIOC), 28 Jan-2 Feb 2007. (Conference Contribution - Oral presentation)
  • Abell, A.D., Coxon, J.M., Miyamoto, S., Jones, M.A., Neffe, A.T., Aitken, S.G., Stuart, B.G., Nikkel, J.M., Morton, J.D., Bickerstaffe, R., Robertson, L.J., Lee, H.L. and Muir, M.S. (2006) Calpain compounds and compositions. Patent No. 547303, New Zealand. (Intellectual Property)
  • Abell, A.D., Aitken, S.G., Coxon, J.M., Jones, M.A., Lee, H.Y-Y., McNabb, S.B., Morton, J.D., Neffe, A.T., Nikkel, J.M., Robertson, L.J.G. and Stuart, B.G. (2006) The Molecular Modelling of µ-Calpain and in-silico Design of Calpain Inhibitors. Rotorua, New Zealand: NZIC Conference 2006 "Back to the Basics: From Small Molecules to Materials and Surfaces", 2-6 Dec 2006. In Proceedings of the NZIC 2006 I - Talks 156. (Conference Contribution - Oral presentation)
  • Jones, S., Abell, A., Coxon, J., Aitken, S. and Jones, M. (2006) β-Sheet Mimics as a Basis for the Synthesis of Novel Protease Inhibitors. Rotorua, New Zealand: NZIC Conference 2006 "Back to the Basics: From Small Molecules to Materials and Surfaces", 2-6 Dec 2006. In Proceedings of the NZIC 2006 II - Posters 46. (Conference Contribution - Poster presentation)
  • Coxon, J.M., Abell, A.D., Miyamoto, S., Stuart, B.G., Neffe, A.T., Jones, M.A., Bickerstaffe, R. and Morton, J. (2005) Cataract Research at Canterbury (Invited lecture). Victoria University, Wellington: Halton Symposium on Novel Molecules, New Materials, and Small Rings, 29-30 Jun 2005. (Conference Contribution - Oral presentation)
  • Neffe, A.T., Abell, A.D., Coxon, J.M., Jones, M.A., Myamoto, S., Nikkel, J.M., Payne, R.J. and Stuart, B.G. (2005) Synthesis and modelling studies of peptidomimetic aldehydes related to a cataract preventing calpain inhibitor. Steamboat Springs, CO, USA: 6th Winter Conference on Bioorganic and Medicinal Chemistry, 23-28 Jan 2005. (Conference Contribution - Oral presentation)
  • Neffe, A.T., Jones, M.A., Stuart, B.G., Abell, A.D., Coxon, J.M., Payne, R.J., Myamoto, S., Lee, H.Y.-Y., Robertson, L.J.G. and Morton, J.D. (2005) Synthesis and modelling studies of peptidomimetic calpain inhibitors for cataract treatment. Dusseldorf, Germany: Annual Meeting of the Society of German Chemists, 11-14 Sep 2005. (Conference Contribution - Oral presentation)
  • Coxon, J.M., Cambridge, J.R.A. and Nam, S.G.C. (2004) Identification of beta-Prochiral Protons to the Ether Oxygen of Chiral Esters of 2-Arylethan-1-ols with d-Yb(hfc)3 Shift Reagents. Synlett (7): 1422-1455. (Journal Article)
  • Marchand, A.P. and Coxon, J.M. (2002) On the Origins of Diastereofacial Selectivity of [4 + 2] Cycloadditions in Cage-Annulated and Polycarbocyclic Diene/Dienophile Systems. Invited Review. Accounts of Chemical Research 35: 271-277. (Journal Article)
  • Coxon, J.M., Cambridge, J.R.A. and Nam, S.G.C. (2001) Nmr seperation of beta-prochiral protons to the ether oxygen of chiral esters with lanthanide shift reagents. Organic Letters 3: 4224-4227. (Journal Article)
  • Coxon, J.M. and Thorpe, A.J. (2000) A density functional theory study of the mechanism of the BF3-catalysed rearrangement of 2, 3, 3-trimethyl-1, 2-epoxybutane to 2, 3, 3-trimethylbutanal. J. Org. Chem 65(25): 8421-9. (Journal Article)
  • (2000) Organic synthesis using transition metals. Sheffield: Sheffield Academic Press Blackwell Science. 200. (Edited Book)
  • (2000) Organic Synthesis with Carbohydrates. Sheffield: Sheffield Academic Press Blackwell Science. 336. (Edited Book)
  • Marchand, A.P., Chong, H-Y., Ganguly, B. and Coxon, J.M. (2000) Pi-facial Selectivity in Diels Alder Cycloadditions. Croat. Chem. Acta 73(4): 1027-1038. (Journal Article)
  • Coxon, J.M. and Luibrand, R.T. (2000) Pi-Facial selectivity in reaction of carbonyls: a computational approach. In Otera, J. (Ed.), Modern Carbonyl Chemistry: 155-84. Weinhein Germany: Wiley-VCH. (Chapter in Book)
  • Coxon, J.M. and Smith, W.B. (2000) Polar bromination of cyclopropane: A DFT study. J. Org. Chem 65(7): 2192-4. (Journal Article)
  • (2000) Stoichiometric Asymmetric Synthesis. Sheffield: Sheffield Academic Press, Blackwell Science. 236. (Edited Book)
  • Coxon, J.M. and Thorpe, A.J. (1999) An ab initio study of intramolecular ring cyclisation of protonated and BF3 coordinated trans- and cis-4, 5-epoxyhexan-1-ol. J. Org. Chem. 64: 5530-41. (Journal Article)
  • (1999) Catalysis in asymmetric synthesis. University of Bath: Sheffield Academic Press. 198. (Edited Book)
  • Coxon, J.M., Froese, R.D.J., Ganguly, B., Marchand, A.P. and Morokuma, K. (1999) On the origins of diastereofacial selectivity in Diels-Alder cycloadditions. Synlet 11: 1681-1703. (Journal Article)
  • (1999) Protecting groups. Sheffield: Sheffield Academic Press, Blackwell Science. 130. (Edited Book)
  • Coxon, J.M., Thorpe, A.J. and Smith, W.B. (1999) The potential energy surface for the acid and BF3 catalysed rearrangement of methylpropene epoxide. J. Org. Chem 64(26): 9575-86. (Journal Article)
  • Coxon, J.M. and Thorpe, A.J. (1999) Theozymes for intramolecular ring cyclisation reactions. J. Am. Chem. Soc 121(47): 10955-7. (Journal Article)
  • Coxon, J.M., Morokuma, K., Thorpe, A.J. and Whalen, D. (1998) Molecular orbital studies of intramolecular reaction of protonated cis- and trans- 3, 4-epoxypentan-1-ol. J. Org. Chem 1998(63): 3875-83. (Journal Article)
  • Coxon, E.E., Coxon, J.M. and Boswell, D.R. (1998) The correlation of carbohydrate molecular motion with nOe buildup spectra. Aust. J. Chem 1998(51): 397-401. (Journal Article)
  • Coxon, J.M. and Gerrard, J.A. (1998) Worked Solutions in Organic Chemistry. London: Blackie Academic & Professional, an Imprint of Chapman and Hall. 516pp. (Authored Book)
  • Patterson, S.E., Coxon, J.M. and Strekowski, L. (1997) Intercalation of Ethidium and Analogues with Nucleic Acids: A Molecular Orbital study. Biorganic and Medicinal Chemistry 5: 277-281. (Journal Article)
  • Coxon, J.M., MacLagan, R.G.A.R., Rauk, A., Thorpe, A.J. and Whalen, D. (1997) Rearrangement of protonated propene oxide to protonated propanal. J. Am. Chem. Soc 119: 4712-8. (Journal Article)
  • Froese, R.D.J., Coxon, J.M., West, S.C. and Morokuma, K. (1997) Theoretical studies of Diels-Alder reactions of acetylenic compounds. J. Org. Chem. 62: 6991-6. (Journal Article)