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Dr Eng Wui Tan

eng_tanPhD, BSc(Adel)

Tel: 03 479 7926
Location: Science II, 2n9
Email: ewtan@chemistry.otago.ac.nz

Research Interests

Interactions of Molecules with Enzymes and Directing Effects of Substituents in Radical Reactions

Part of my research group is involved in the study of enzyme interactions with unusual molecules. Various enzymes are under study, with families of synthetic molecules, in an attempt to correlate enzyme behavior with peculiar molecular structure and conformation. Transient and steady-state techniques are employed. It is our hope that this research will reveal unusual structural motifs that can be incorporated into the design of enzyme inhibitors and structural sensors. In collaboration with Dr. Keith Gordon, we are exploring the use of laser spectroscopy in some enzyme systems through diazo molecular probes.

My research group is also interested in selective radical reactions as they allow the introduction of chemical functionality to otherwise featureless substructures for further manipulation. This technique is particularly applicable to chiral pool compounds as it simplifies the synthesis of enantiomerically pure molecules. Selectivity in radical reactions can be achieved through the use of directing substituents which either activate or inactivate a particular position or stereochemical aspect. For example, the following reaction proceeds with >95% ee in quantitative yield via a bridged chlorine radical intermediate.

We are also trying to capture the imagination of students and the general public by representing molecular structure and function in exciting new ways.

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Publications

Wilson, S., Laing, R., Tan, E. W., & Wilson, C. (2020). Encapsulation of electrically conductive apparel fabrics: Effects on performance. Sensors, 20, 4243. doi: 10.3390/s20154243

Mackay, S. M., Tan, E. W., & Warren, D. S. (2020). Developing a new generation of scientist communicators through effective public outreach. Communications Chemistry, 3, 76. doi: 10.1038/s42004-020-0315-0

Mackay, S. M., Myint, D. M. A., Easingwood, R. A., Hegh, D. Y., Wickens, J. R., Hyland, B. I., Jameson, G. N. L., Reynolds, J. N. J., & Tan, E. W. (2019). Dynamic control of neurochemical release with ultrasonically-sensitive nanoshell-tethered liposomes. Communications Chemistry, 2, 122. doi: 10.1038/s42004-019-0226-0

Tan, E. W., Mackay, S., Nakano, T., Reynolds, J. N. J., & Wickens, J. (2018, August). Pulse-modulation drug delivery from lipsomal nanostructures. Verbal presentation at the Queenstown Molecular Biology (QMB) Meetings, Queenstown, New Zealand.

Vautrelle, N., Bergin, D. H., Gray, J. P., Bergin, R., Leriche, M., Fuller, J., Hyland, B. I., … Tan, E. W., & Reynolds, J. N. J. (2018). Development of a minimally-invasive technology for spatially- and temporally-controlled drug delivery into the brain. In K. Hillman (Ed.), Proceedings of the 36th International Australasian Winter Conference on Brain Research. (pp. 66). AWCBR. Retrieved from https://www.otago.ac.nz/awcbr

Wilson, S., Laing, R., Tan, E. W., & Wilson, C. (2020). Encapsulation of electrically conductive apparel fabrics: Effects on performance. Sensors, 20, 4243. doi: 10.3390/s20154243

Journal - Research Article

Mackay, S. M., Myint, D. M. A., Easingwood, R. A., Hegh, D. Y., Wickens, J. R., Hyland, B. I., Jameson, G. N. L., Reynolds, J. N. J., & Tan, E. W. (2019). Dynamic control of neurochemical release with ultrasonically-sensitive nanoshell-tethered liposomes. Communications Chemistry, 2, 122. doi: 10.1038/s42004-019-0226-0

Journal - Research Article

Hegh, D. Y., Mackay, S. M., & Tan, E. W. (2016). Pulsatile release from pH triggered imidazoline switchable surfactant liposomes. RSC Advances, 6, 56859-56866. doi: 10.1039/c6ra08814g

Journal - Research Article

Hinow, P., Radunskaya, A., Mackay, S. M., Reynolds, J. N. J., Schroeder, M., Tan, E. W., & Tucker, I. G. (2016). Signaled drug delivery and transport across the blood-brain barrier. Journal of Liposome Research, 26(3), 233-245. doi: 10.3109/08982104.2015.1102277

Journal - Research Article

Nakano, T., Mackay, S. M., Tan, E. W., Dani, K. M., & Wickens, J. (2016). Interfacing with neural activity via femtosecond laser stimulation of drug-encapsulating liposomal nanostructures. eNeuro, 3(6), e0107-16.2016. doi: 10.1523/ENEURO.0107-16.2016

Journal - Research Article

Rodpun, K., Lucas, N. T., Tan, E. W., & Meledandri, C. J. (2016). Development of solvent-dispersible coordination polymer nanocrystals and application as efficient heterogeneous catalysts. Crystal Growth & Design, 16(7), 3940-3946. doi: 10.1021/acs.cgd.6b00502

Journal - Research Article

Smith, R. J., Mills, D. A., Nhu, D., Tan, E. W., Lucas, N. T., & Hawkins, B. C. (2016). The synthesis of multifunctionalized 1,3-oxazin-4-ones from donor-acceptor cyclopropanes. Journal of Organic Chemistry, 81(5), 2099-2105. doi: 10.1021/acs.joc.6b00112

Journal - Research Article

Craig, A. J., van der Salm, L., Stevens-Cullinane, L., Lucas, N. T., Tan, E. W., & Hawkins, B. C. (2015). Expedient metal-free synthesis of 1,3-oxazinen-4-ones. Organic Letters, 17(2), 234-237. doi: 10.1021/ol503350h

Journal - Research Article

Rodpun, K., Blackman, A. G., Gardiner, M. G., Tan, E. W., Meledandri, C. J., & Lucas, N. T. (2015). Alkyl linker effects on the coordination topology of ditopic di(2-pyridylmethyl)amine carboxylate ligands with ZnII and CuII: Polymers vs. macrocycles. CrystEngComm, 17(15), 2974-2988. doi: 10.1039/c5ce00375j

Journal - Research Article

Hegh, D. Y., Mackay, S. M., & Tan, E. W. (2014). CO2-triggered release from switchable surfactant impregnated liposomes. RSC Advances, 4, 31771-31774. doi: 10.1039/c4ra05387g

Journal - Research Article

Nakano, T., Chin, C., Myint, D. M. A., Tan, E. W., Hale, P. J., Krishna M, B. M., Reynolds, J. N. J., … Dani, K. M. (2014). Mimicking subsecond neurotransmitter dynamics with femtosecond laser stimulated nanosystems. Scientific Reports, 4, 5398. doi: 10.1038/srep05398

Journal - Research Article

Jordan, D., Tan, E., & Hegh, D. (2012). Synthesis, characterization and conductivity of quaternary nitrogen surfactants modified by the addition of a hydroxymethyl substrate on the head group. Journal of Surfactants & Detergents, 15(5), 587-592. doi: 10.1007/s11743-012-1360-1

Journal - Research Article

Tong, A. Y. C., Braund, R., Tan, E. W., Tremblay, L. A., Stringer, T., Trought, K., & Peake, B. M. (2011). UV-induced photodegradation of oseltamivir (Tamiflu) in water. Environmental Chemistry, 8(2), 182-189. doi: 10.1071/EN10095

Journal - Research Article

Jordan, D. K., Kitchen, J. A., Hegh, D. Y., Brooker, S., & Tan, E. W. (2008). 1-Tetradecylpyridinium bromide monohydrate. Acta Crystallographica Section E, E64, o2457-02457.

Journal - Research Article

Gao, Z., Bremer, P. J., Barker, M. F., Tan, E. W., & McQuillan, A. J. (2007). Adhesive secretions of live mussels observed in Situ by attenuated total reflection-infrared spectroscopy. Applied Spectroscopy, 61(1), 55-59.

Journal - Research Article

Myint, M. A., Price, J. R., & Tan, E. W. (2006). Adamantane-1,2-diol. Acta Crystallographica Section E, E62, o1139-o1140.

Journal - Research Article

Bailey, K., & Tan, E. W. (2005). Synthesis and evaluation of bifuntional nitrocatechol inhibitors of pig liver carechol-O-methyltranferase. Bioorganic & Medicinal Chemistry, 13, 5740-5749.

Journal - Research Article

Myint, M. A., Blackman, A. G., & Tan, E. W. (2005). (±)-Adamantane-1,2-diyl diacetate. Acta Crystallographica Section E, 61, 3154-3155. doi: 10.1107/S1600536805027509

Journal - Research Article

Yu, P.-S., Thomas, G. D., Blackman, A. G., & Tan, E. W. (2005). trans-3-Bromo-2-chloroindan-1-one. Acta Crystallographica Section E, 61, 0651-0652.

Journal - Research Article

Bailey, K., Cowling, R., Tan, E. W., & Webb, D. (2004). A colormetric assay for catechol-O-methyltransferase. Bioorganic & Medicinal Chemistry, 12, 595-601.

Journal - Research Article

Haghbeen, K., & Tan, E. W. (2003). Direct spectrophotometric assay of monooxygenase and oxidase activities of mushroom tyrosinase in the presence of synthetic and natural substrates. Analytical Biochemistry, 312(1), 23-32.

Journal - Research Article

Tan, E. W., Chan, B., & Blackman, A. G. (2002). A polar Effects Controlled Enantioselective 1,2-Chlorine Atom Migration via a Chlorine-Bridged Radical Intermediate. Journal of the American Chemical Society, 124(10), 2078-2079.

Journal - Research Article

Chan, B., Tan, E. W., & Blackman, A. G. (2001). Pentafluorophenyl 3-chloro-3-phenylpropanoate. Acta Crystallographica Section E, E57, o725-o726.

Journal - Research Article

Chan, B., Wong, E., Simpson, J., & Tan, E. W. (2000). (+)-(2R,3S)-3-bromo-2-chloro-N,N-diisopropyl-3-phenylpropanamide and (+)-(2R,3S)-3-bromo-2-chloro-N-(4-nitrophenyl)-3-phenylpropanamide. Acta Crystallographica Section C, 56, 354-355.

Journal - Research Article

Wong, E., Chan, B., & Tan, E. W. (2000). Stereoselective radical bromination of α-chloro hydrocinnamic acid derivatives. Tetrahedron Letters, 41, 2671-2674.

Journal - Research Article

Haghbeen, K., & Tan, E. W. (1998). Facile synthesis of catechol azo dyes. Journal of Organic Chemistry, 63, 4503-4505.

Journal - Research Article

Brevitt, S. E., & Tan, E. W. (1997). Synthesis and in vitro evaluation of two progressive series of bifunctional polyhydroxybenzamide catechol-O-methyltransferase inhibitors. Journal of Medicinal Chemistry, 40(13), 2035-2039.

Journal - Research Article

Shaw, J. P., & Tan, E. W. (1996). Selective bromination of α-chloro and α-bromo carboxylic acid derivatives. Journal of Organic Chemistry, 61(16), 5635-5637. doi: 10.1021/jo960311l

Journal - Research Article

Shaw, J. P., Tan, E. W., & Blackman, A. G. (1996). Methyl 2-Benzoyloxy-3-oxo-3-phenylpropanoate. Acta Crystallographica Section C, 52(11), 2883-2885. doi: 10.1107/S0108270196008323

Journal - Research Article

Mackay, S. M., Tan, E. W., & Warren, D. S. (2020). Developing a new generation of scientist communicators through effective public outreach. Communications Chemistry, 3, 76. doi: 10.1038/s42004-020-0315-0

Journal - Research Other

Nakano, T., Chin, C., Myint, D. M. A., Tan, E. W., Hale, P. J., Reynolds, J. N. J., Wickens, J., & Dani, K. M. (2014). Femtosecond laser stimulated nanosystems for neuroscience applications. Proceedings of the Conference on Lasers and Electro-Optics (CLEO): Applications and Technology: Symposium on Novel Light Sources and Photonic Devices in Optical Imaging I. Optical Society. doi: 10.1364/CLEO_AT.2014.ATu2P.6

Conference Contribution - Published proceedings: Full paper

Vautrelle, N., Bergin, D. H., Gray, J. P., Bergin, R., Leriche, M., Fuller, J., Hyland, B. I., … Tan, E. W., & Reynolds, J. N. J. (2018). Development of a minimally-invasive technology for spatially- and temporally-controlled drug delivery into the brain. In K. Hillman (Ed.), Proceedings of the 36th International Australasian Winter Conference on Brain Research. (pp. 66). AWCBR. Retrieved from https://www.otago.ac.nz/awcbr

Conference Contribution - Published proceedings: Abstract

Craig, A. J., Smith, R., Stevens-Cullinane, L., Lucas, N. T., Tan, E. W., & Hawkins, B. C. (2016). The synthesis of multifunctionalised 1,3-oxazin-4-enones from 1-acyl-1-cyclopropyl carboxylic acids. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Conference Contribution - Published proceedings: Abstract

Craig, A., Smith, R., Stevens-Cullinane, L., Lucas, N. T., Tan, E. W., & Hawkins, B. C. (2016). The synthesis of multifunctionalised 1,3-oxazin-4-Enones from 1-acyl-1-cyclopropyl carboxylic acids. Proceedings of the Diagnostics, Drugs, Devices, Discovery (D4) Conference. Retrieved from http://www.otago.ac.nz/d4/index.html

Conference Contribution - Published proceedings: Abstract

Mackay, S. M., & Tan, E. W. (2016). Spatiotemporal neural modulation by liposomal nanostructures. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Conference Contribution - Published proceedings: Abstract

Rodpun, K., Lucas, N. T., Tan, E. W., & Meledandri, C. J. (2016). Colloidal coordination polymer nanocrystals: Synthesis and catalytic activity. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Conference Contribution - Published proceedings: Abstract

Smith, R. J., Craig, A. J., Tan, E. W., Lucas, N. T., & Hawkins, B. C. (2016). Expedient synthesis of 1,3-oxazin-4-ones. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Retrieved from http://www.nzic16.org/

Conference Contribution - Published proceedings: Abstract

Braund, R., Tong, A., Tan, E., Tremblay, L., Stringer, T., & Peake, B. (2014). Photodegradation of oseltamivir (Tamiflu™) in aqueous solution. Proceedings of the 5th Pharmaceutical Sciences World Congress (PSWC). Retrieved from http://www.fip.org/pswc2014/Melbourne/2041/Programme/

Conference Contribution - Published proceedings: Abstract

Hegh, D. Y., Mackay, S. M., & Tan, E. W. (2013). pH-triggered release from 2-alkylimidazoline surfactant impregnated liposomes. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Christchurch, New Zealand: NZIC. [Abstract]

Conference Contribution - Published proceedings: Abstract

Mackay, S. M., Hegh, D. Y., & Tan, E. W. (2013). UV-triggered release from switchable surfactant impregnated liposomes. Proceedings of the New Zealand Institute of Chemistry (NZIC) Conference. Christchurch, New Zealand: NZIC. [Abstract]

Conference Contribution - Published proceedings: Abstract

Hegh, D. Y., Tan, E. W., & Jordan, D. K. (2011). Manipulation of vesicle morphology by quaternary ammonium cationic surfactants. Proceedings of the Fifth International Conference on Advanced Materials and Nanotechnology (AMN-5). Retrieved from http://www.confer.co.nz/amn-5/pdf/Posters/FP44.pdf

Conference Contribution - Published proceedings: Abstract

Jordan, K., Hegh, D. Y., Tan, E. W., & Bremer, P. (2008). Synthesis and study of Quaternary Nitrogen Species. Proceedings of the New Zealand Microbiological Society Microbiology Conference. (pp. 34). NZMS. Retrieved from http://www.nzmsconference08.org.nz/files/Poster-Abstracts-NZMS-2008.pdf

Conference Contribution - Published proceedings: Abstract

Jordan, D. K., Tan, E. W., Hegh, D. Y., McQuillan, A. J., Bremer, P. J., Kennedy, M. J., Seale, R. B., & Bailey, K. B. (2006). Synthesis and study of quaternary nitrogen centres for use in surface antibiofouling coatings. In M. Lein (Ed.), Proceedings of the New Zealand Institute of Chemistry Conference. II, (pp. 167). Christchurch, New Zealand: NZIC. [Abstract]

Conference Contribution - Published proceedings: Abstract

Bremer, P., Gao, J., Barker, M., Tan, E. W., & McQuillan, J. (2004). Observing mussel adhesion secretions with in situ infrared spectroscopy. Proceedings of the NZMSS 2004 Conference. (pp. 4). [Abstract]

Conference Contribution - Published proceedings: Abstract

Tan, E. W., & Shaw, J. P. (1997). Controlling selectivity of radical reactions in a substituted carboxylic acid derivatives. Proceedings of the 35th National Organic Conference. (pp. W338). [Abstract]

Conference Contribution - Published proceedings: Abstract

Tan, E. W., & Shaw, J. P. (1997). Controlling stereoselectivity in free radical brominations of alpha-substituted carboxylic acids. 35th National Organic Chemistry Symposium, June 22-26, 1997, Trinity University, San Antonio, Texas. San Antonio, USA. [Abstract]

Conference Contribution - Published proceedings: Abstract

Bailey, K. B., & Tan, E. W. (1996). Polyfunctional competitive substrates/inhibitors of catechol-o-methyltransferase. Molecules for the Future: National Conference of the New Zealand Institute of Chemistry and the New Zealand Society of Biochemistry and Molecular Biology, University of Otago, Dunedin, 2-6 December 1996: Programme and Abstracts. (pp. 128). Dunedin: The Institute. [Abstract]

Conference Contribution - Published proceedings: Abstract

Haghbeen, K., & Tan, E. W. (1996). A facile method for synthesising Diazo Catechol dyes used as chromophoric substrates for tyrosinase. Molecules for the Future: National Conference of the New Zealand Institute of Chemistry and the New Zealand Society of Biochemistry and Molecular Biology, University of Otago, Dunedin, 2-6 December 1996: Programme and Abstracts. (pp. 64). Dunedin: The Institute. [Abstract]

Conference Contribution - Published proceedings: Abstract

Tan, E. W., & Shaw, J. P. (1996). Controlling selectivity of radical reactions in alpha-substituted carboxylic acid derivatives. Molecules for the Future: National Conference of the New Zealand Institute of Chemistry and the New Zealand Society of Biochemistry and Molecular Biology, University of Otago, Dunedin, 2-6 December 1996: Programme and Abstracts. (pp. 56). Dunedin: The Institute. [Abstract]

Conference Contribution - Published proceedings: Abstract

Tan, E. W., & Thomas, G. D. (1996). Exploring selective radical functionalisation of cyclic alpha-amino acid derivatives. Molecules for the Future: National Conference of the New Zealand Institute of Chemistry and the New Zealand Society of Biochemistry and Molecular Biology, University of Otago, Dunedin, 2-6 December 1996: Programme and Abstracts. (pp. 105). Dunedin: The institute. [Abstract]

Conference Contribution - Published proceedings: Abstract

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