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Professor David Larsen

david_larsenPhD, MSc(Auck)

Tel: 03 479 7816
Location: Science II, 2n11
Email: dlarsen@chemistry.otago.ac.nz

Research Interests

My research interests are primarily in the development of methodology the syntheses of natural products and also in the area of the synthesis of carbohydrates, glycolipids and their analogues.

On-going research projects are:

  • Structure, synthesis and biological activity of phosphatidylinositol mannosides from mycobacterium tuberculosis
  • Glycolipids as adjuvants for cancer vaccines
  • Total synthesis of the angucycline antibiotics
  • Carbon monoxide releasing molecules for organ transplant solutions
  • Mannosylation of Virus Like Particles
  • Bacterial cell wall skeletons as transporters of small molecules to APCs

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Publications

Johnston, H. M., Kueh, J. T. B., Hartley, R. H., Bland, A. R., Payne, F. M., Harrison, J. C., Sammut, I. A., & Larsen, D. S. (2022). Utilising fluorescent reporters to probe the mode of action of norbornen-7-one CO releasing molecules. Organic & Biomolecular Chemistry. Advance online publication. doi: 10.1039/d2ob01076c

Sammut, I. A., Harrison, J. C., Hewitt, R. J., Read, M. I., Stanley, N. J., Woods, L. M., Kueh, J. T. B., … Smith, R. A. J., Giles, G., … Larsen, D. S. (2021). Carbon monoxide releasing norbornenone compounds. (11072584). United States.

McDougall, L., Kueh, J. T. B., Ward, J., Tyndall, J. D. A., Woolley, A. G., Mehta, S., Stayner, C., Larsen, D. S., & Eccles, M. R. (2021). Chemical synthesis of the PAX protein inhibitor EG1 and its ability to slow the growth of human colorectal carcinoma cells. Frontiers in Oncology, 11, 709540. doi: 10.3389/fonc.2021.709540

Thwaite, S. H., Read, M. I., Larsen, D. S., Harrison, J. C., & Sammut, I. A. (2021). Can carbon monoxide protect hypertrophic hearts against ischaemia-reperfusion injury. New Zealand Medical Journal, 134(1535), (pp. 98). Retrieved from https://www.nzma.org.nz/journal

Richardson, A. T., McGhie, T. K., Cordiner, S. B., Stephens, T. T. H., Larsen, D. S., Laing, W. A., & Perry, N. B. (2021). 2-O-β-d-Glucopyranosyl L-ascorbic acid, a stable form of vitamin C, is widespread in crop plants. Journal of Agricultural & Food Chemistry, 69, 966-973. doi: 10.1021/acs.jafc.0c06330

Johnston, H. M., Kueh, J. T. B., Hartley, R. H., Bland, A. R., Payne, F. M., Harrison, J. C., Sammut, I. A., & Larsen, D. S. (2022). Utilising fluorescent reporters to probe the mode of action of norbornen-7-one CO releasing molecules. Organic & Biomolecular Chemistry. Advance online publication. doi: 10.1039/d2ob01076c

Journal - Research Article

McDougall, L., Kueh, J. T. B., Ward, J., Tyndall, J. D. A., Woolley, A. G., Mehta, S., Stayner, C., Larsen, D. S., & Eccles, M. R. (2021). Chemical synthesis of the PAX protein inhibitor EG1 and its ability to slow the growth of human colorectal carcinoma cells. Frontiers in Oncology, 11, 709540. doi: 10.3389/fonc.2021.709540

Journal - Research Article

Richardson, A. T., McGhie, T. K., Cordiner, S. B., Stephens, T. T. H., Larsen, D. S., Laing, W. A., & Perry, N. B. (2021). 2-O-β-d-Glucopyranosyl L-ascorbic acid, a stable form of vitamin C, is widespread in crop plants. Journal of Agricultural & Food Chemistry, 69, 966-973. doi: 10.1021/acs.jafc.0c06330

Journal - Research Article

Kueh, J. T. B., Seifert-Simpson, J. M., Thwaite, S. H., Rodgers, G. D., Harrison, J. C., Sammut, I. A., & Larsen, D. S. (2020). Studies towards non-toxic, water soluble, vasoactive norbornene organic carbon monoxide releasing molecules. Asian Journal of Organic Chemistry, 9, 1-10. doi: 10.1002/ajoc.202000546

Journal - Research Article

Richardson, A. T., Cho, J., McGhie, T. K., Larsen, D. S., Schaffer, R. J., Espley, R. V., & Perry, N. B. (2020). Discovery of a stable vitamin C glycoside in crab apples (Malus sylvestris). Phytochemistry, 173, 112297. doi: 10.1016/j.phytochem.2020.112297

Journal - Research Article

Robinson, S. A., Yau, J., Terabe, M., Berzofsky, J. A., Painter, G. F., Compton, B. J., & Larsen, D. S. (2020). Synthetic preparation and immunological evaluation of β-mannosylceramide and related N-acyl analogues. Organic & Biomolecular Chemistry, 18, 2739-2746. doi: 10.1039/d0ob00223b

Journal - Research Article

Kramer, K., Al-Barwani, F., Baird, M. A., Young, V. L., Larsen, D. S., Ward, V. K., & Young, S. L. (2019). Functionalisation of virus-like particles enhances antitumour immune responses. Journal of Immunology Research, 2019, 5364632. doi: 10.1155/2019/5364632

Journal - Research Article

Osman, H., Larsen, D. S., & Muralikrishna, A. (2019). A stereoselective approach to the angucyclinone antibiotics: A total synthesis of (±)-urdamycinone B. Arabian Journal of Chemistry, 12, 2501-2512. doi: 10.1016/j.arabjc.2015.04.022

Journal - Research Article

Payne, C. M., Cho, K., & Larsen, D. S. (2019). 5-Bromo-norborn-2-en-7-one derivatives as a carbon monoxide source for palladium catalyzed carbonylation reactions. RSC Advances, 9, 30736-30740. doi: 10.1039/c9ra06594f

Journal - Research Article

Hogue, R. W., Dhers, S., Hellyer, R. M., Luo, J., Hanan, G. S., Larsen, D. S., Garden, A. L., & Brooker, S. (2017). Self-assembly of cyclohelicate [M3L3] triangles over [M4L4] squares, despite near-linear bis-terdentate L and octahedral M. Chemistry: A European Journal, 23(57), 14193-14199. doi: 10.1002/chem.201702153

Journal - Research Article

Kueh, J. T. B., Stanley, N. J., Hewitt, R. J., Woods, L. M., Larsen, L., Harrison, J. C., … Sammut, I. A., & Larsen, D. S. (2017). Norborn-2-en-7-ones as physiologically-triggered carbon monoxide-releasing prodrugs. Chemical Science, (8), 5454-5459. doi: 10.1039/c7sc01647f

Journal - Research Article

Malthus, S. J., Wilson, R. K., Aggarwal, A. V., Cameron, S. A., Larsen, D. S., & Brooker, S. (2017). Carbazole-based N4-donor Schiff base macrocycles: Obtained metal free and as Cu(II) and Ni(II) complexes. Dalton Transactions, 46(10), 3141-3149. doi: 10.1039/c6dt04598g

Journal - Research Article

Moodie, L. W. K., Trepos, R., Cervin, G., Larsen, L., Larsen, D. S., Pavia, H., … Svenson, J. (2017). Probing the structure-activity relationship of the natural antifouling agent polygodial against both micro- and macrofoulers by semisynthetic modification. Journal of Natural Products, 80(2), 515-525. doi: 10.1021/acs.jnatprod.6b01056

Journal - Research Article

Nhu, D., Larsen, L., Perry, N. B., Larsen, D. S., & Hawkins, B. C. (2017). Sweet poisons: Synthetic strategies towards tutin glycosides. Australian Journal of Chemistry, 70(3), 301-306. doi: 10.1071/CH16429

Journal - Research Article

Malthus, S. J., Wilson, R. K., Larsen, D. S., & Brooker, S. (2016). Acridine-based ligands from cobalt(II) mediated rearrangement of diphenylamine-based starting materials. Supramolecular Chemistry, 28(1-2), 98-107. doi: 10.1080/10610278.2015.1091458

Journal - Research Article

Anderson, R. J., Compton, B. J., Tang, C.-W., Authier-Hall, A., Hayman, C. M., Swinerd, G. W., … Larsen, D. S., … Weinkove, R., Hermans, I. F., & Painter, G. F. (2015). NKT cell-dependent glycolipid—peptide vaccines with potent anti-tumour activity. Chemical Science, 6(9), 5095-5312. doi: 10.1039/c4sc03599b

Journal - Research Article

Compton, B. J., Tang, C.-W., Johnston, K. A., Osmond, T. O., Hayman, C. M., Larsen, D. S., Hermans, I. F., & Painter, G. F. (2015). Synthesis and activity of 6''-Deoxy-6''-thio-α-GalCer and peptide conjugates. Organic Letters, 17, 5954-5957. doi: 10.1021/acs.orglett.5b02836

Journal - Research Article

Finichiu, P. G., Larsen, D. S., Evans, C., Larsen, L., Bright, T. P., Robb, E. L., … Smith, R. A. J., & Murphy, M. P. (2015). A mitochondria-targeted derivative of ascorbate: MitoC. Free Radical Biology & Medicine, 89, 668-678. doi: 10.1016/j.freeradbiomed.2015.07.160

Journal - Research Article

Jiménez-Dalmaroni, M. J., Radcliffe, C. M., Harvey, D. J., Wormald, M. R., Verdino, P., Ainge, G. D., Larsen, D. S., … Wilson, I. A. (2015). Soluble human TLR2 ectodomain binds diacylglycerol from microbial lipopeptides and glycolipids. Innate Immunity, 21(2), 175-193. doi: 10.1177/1753425914524077

Journal - Research Article

Kueh, J. T. B., Moodie, L. W. K., Lucas, N. T., & Larsen, D. S. (2015). Synthesis of acyloxy-semicyclic dienes using an enyne metathesis/ring closing metathesis approach. European Journal of Organic Chemistry, 2015(7), 1485-1490. doi: 10.1002/ejoc.201403482

Journal - Research Article

Mainini, F., Larsen, D. S., Webster, G. A., Young, S. L., & Eccles, M. R. (2015). Bridging small molecules to modified bacterial microparticles using a disulphide linkage: MIS416 as a cargo delivery system. PLoS ONE, 10(12), e0145403. doi: 10.1371/journal.pone.0145403

Journal - Research Article

Zheng, T., Luo, D., Compton, B. J., Painter, G. F., Alley, M. R., Larsen, D. S., … Heiser, A. (2015). Adjuvanticity of a synthetic phosphatidylinositol dimannoside to a subvirion influenza vaccine in an influenza mouse model. Journal of Vaccines & Vaccination, 6(2), 1000277. doi: 10.4172/2157-7560.1000277

Journal - Research Article

Al-Barwani, F., Young, S. L., Baird, M. A., Larsen, D. S., & Ward, V. K. (2014). Mannosylation of virus-like particles enhances internalization by antigen presenting cells. PLoS ONE, 9(8), e104523. doi: 10.1371/journal.pone.0104523

Journal - Research Article

Anderson, R. J., Tang, C.-w., Daniels, N. J., Compton, B. J., Hayman, C. M., Johnston, K. A., … Larsen, D. S., … Hermans, I. F. (2014). A self-adjuvanting vaccine induces cytotoxic T lymphocytes that suppress allergy. Nature Chemical Biology, 10, 943-949. doi: 10.1038/nchembio.1640

Journal - Research Article

Hubert, M., Larsen, D. S., Hayman, C. M., Rades, T., & Hook, S. (2014). Physical characterization of synthetic phosphatidylinositol dimannosides and analogues in binary systems with phosphatidylcholine. Molecular Pharmaceutics, 11(3), 913-921. doi: 10.1021/mp400588y

Journal - Research Article

Lee, A. M. M., Painter, G. F., Compton, B. J., & Larsen, D. S. (2014). Resolution of orthogonally protected myo-inositols with Novozym 435 providing an enantioconvergent Pathway to Ac2PIM1. Journal of Organic Chemistry, 79(22), 10916-10931. doi: 10.1021/jo5019188

Journal - Research Article

Moodie, L. W. K., & Larsen, D. S. (2014). A ring-closing enyne metathesis approach to functionalized semicyclic dienes: The total synthesis of (–)-tetrangomycin. European Journal of Organic Chemistry, 2014(8), 1684-1694. doi: 10.1002/ejoc.201301627

Journal - Research Article

Nakatani, Y., Larsen, D. S., Cutfield, S. M., & Cutfield, J. F. (2014). Major change in regiospecificity for the exo-1,3-β-glucanase from Candida albicans following its conversion to a glycosynthase. Biochemistry, 53(20), 3318-3326. doi: 10.1021/bi500239m

Journal - Research Article

Pun, P. B. L., Logan, A., Darley-Usmar, V., Chacko, B., Johnson, M. S., Huang, G. W., … Larsen, L., Larsen, D. S., … Smith, R. A. J., & Murphy, M. P. (2014). A mitochondria-targeted mass spectrometry probe to detect glyoxals: Implications for diabetes. Free Radical Biology & Medicine, 67, 437-450. doi: 10.1016/j.freeradbiomed.2013.11.025

Journal - Research Article

Hubert, M., Compton, B. J., Hayman, C. M., Larsen, D. S., Painter, G. F., Rades, T., & Hook, S. (2013). Physicochemical and biological characterization of synthetic phosphatidylinositol dimannosides and analogues. Molecular Pharmaceutics, 10(5), 1928-1939. doi: 10.1021/mp300707a

Journal - Research Article

Logan, A., Cochemé, H. M., Li Pun, P. B., Apostolova, N., Smith, R. A. J., Larsen, L., Larsen, D. S., … Murphy, M. P. (2013). Using exomarkers to assess mitochondrial reactive species in vivo. Biochimica et Biophysica Acta: General Subjects, 1840(2), 923-930. doi: 10.1016/j.bbagen.2013.05.026

Journal - Research Article

Rankin, G. M., Maxwell-Cameron, I., Painter, G. F., & Larsen, D. S. (2013). The Dimethoxyphenylbenzyl Protecting Group: An alternative to the p-methoxybenzyl group for protection of carbohydrates. Journal of Organic Chemistry, 5264-5272. doi: 10.1021/jo4004184

Journal - Research Article

Rankin, G. M., Compton, B. J., Johnston, K. A., Hayman, C. M., Painter, G. F., & Larsen, D. S. (2012). Synthesis and mass spectral characterization of mycobacterial phosphatidylinositol and its dimannosides. Journal of Organic Chemistry, 77(16), 6743-6759. doi: 10.1021/jo301189y

Journal - Research Article

Ainge, G. D., Compton, B. J., Hayman, C. M., Martin, W. J., Toms, S. M., Larsen, D. S., Harper, J. L., & Painter, G. F. (2011). Chemical synthesis and immunosuppressive activity of dipalmitoyl phosphatidylinositol hexamannoside. Journal of Organic Chemistry, 76(12), 4941-4951. doi: 10.1021/jo200588u

Journal - Research Article

Ainge, G. D., Martin, W. J., Compton, B. J., Hayman, C. M., Larsen, D. S., Yoon, S.-I., … Painter, G. F. (2011). Synthesis and toll-like receptor 4 (TLR4) activity of phosphatidylinositol dimannoside analogues. Journal of Medicinal Chemistry, 54(20), 7268-7279. doi: 10.1021/jm2008419

Journal - Research Article

Feltham, H. L. C., Klöwer, F., Cameron, S. A., Larsen, D. S., Lan, Y., Tropiano, M., … Powell, A. K., & Brooker, S. (2011). A family of 13 tetranuclear zinc(II)-lanthanide(III) complexes of a [3 + 3] Schiff-base macrocycle derived from 1‚4-diformyl-2‚3-dihydroxybenzene. Dalton Transactions, 40, 11425-11432. doi: 10.1039/c1dt11038a

Journal - Research Article

Harper, J. L., Hayman, C. M., Larsen, D. S., Painter, G. F., & Singh-Gill, G. (2011). A PIM2 analogue suppresses allergic airway disease. Bioorganic & Medicinal Chemistry, 19, 2, 917-925. doi: 10.1016/j.bmc.2010.11.058

Journal - Research Article

Kitchen, J. A., Larsen, D. S., & Brooker, S. (2010). Alkylations of N4-(4-Pyridyl)-3,5-di(2-pyridyl)-1,2,4-triazole: First observation of room-temperature rearrangement of an N4-substituted triazole to the N1 analogue. Chemistry: An Asian Journal, 5(4), 910-918. doi: 10.1002/asia.200900485

Journal - Research Article

Denis, M., Ainge, G. D., Larsen, D. S., Severn, W. B., & Painter, G. F. (2009). A synthetic analogue of phosphatidylinositol mannoside is an efficient adjuvant. Immunopharmacology & Immunotoxicology, 31(4), 577-582. doi: 10.3109/08923970902824862

Journal - Research Article

Driessen, N. N., Ummels, R., Maaskant, J. J., Gurcha, S. S., Besra, G. S., Ainge, G. D., Larsen, D. S., … Appelmelk, B. J. (2009). Role of phosphatidylinositol mannosides in the interaction between mycobacteria and DC-SIGN. Infection & Immunity, 77(10), 4538-4547. doi: 10.1128/iai.01256-08

Journal - Research Article

Feltham, H. L. C., Larsen, D. S., & Brooker, S. (2009). A hexanuclear iron(III) complex of a hexadentate fully conjugated diimine ligand derived from 1,4-diformyl-2,3-dihydroxybenzene. New Journal of Chemistry, 33, 2001-2003. doi: 10.1039/b9nj00347a

Journal - Research Article

Hellyer, R. M., Larsen, D. S., & Brooker, S. (2009). Cobalt and silver complexes of terdentate pyrazine-based amide ligands and assembly of monocobalt building blocks through a silver connector. European Journal of Inorganic Chemistry, (9), 1162-1171. doi: 10.1002/ejic.200801187

Journal - Research Article

Jimenez-Dalmaroni, M. J., Xiao, N., Corper, A. L., Verdino, P., Ainge, G. D., & Larsen, D. S. (2009). Soluble CD36 ectodomain binds negatively charged diacylglycerol ligands and acts as a co-receptor for TLR2. PLoS ONE, 4(10), e7411. doi: 10.1371/journal.pone.0007411

Journal - Research Article

Osman, H., Larsen, D. S., & Simpson, J. (2009). Synthesis of orthogonally protected D-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-D-arabinopyranose, as a C-glycosyl donor. Tetrahedron, 65(21), 4092-4098. doi: 10.1016/j.tet.2009.03.092

Journal - Research Article

Compton, B. J., Larsen, D. S., Larsen, L., & Weavers, R. T. (2008). Reactive diene for synthesis of substituted catechols. Tetrahedron Letters, 49(2), 219-221. doi: 10.1016/j.tetlet.2007.11.085

Journal - Research Article

Osman, H., Larsen, D. S., Hanton, L. R., & Simpson, J. (2008). Phenyl 2,3-O-isopropylidene-1-thio-α-D-rhamnopyranoside. Acta Crystallographica Section E, E64, o24-o25. doi: 10.1107/S1600536807061004

Journal - Research Article

Parlane, N. A., Denis, M., Severn, W. B., Skinner, M. A., Painter, G. F., La Flamme, A. C., Ainge, G. D., Larsen, D. S., & Buddle, B. M. (2008). Phosphatidylinositol mannosides are efficient mucosal adjuvants. Immunological Investigations, 37(2), 129-142. doi: 10.1080/08820130701690782

Journal - Research Article

Ainge, G. D., Parlane, N. A., Denis, M., Dyer, B. S., Härer, A., Hayman, C. M., Larsen, D. S., & Painter, G. F. (2007). Phosphatidylinositol mannoside ether analogues: Syntheses and interleukin-12-inducing properties. Journal of Organic Chemistry, 72(14), 5291-5296. doi: 10.1021/jo070639m

Journal - Research Article

de Geest, D. J., Noble, A., Moubaraki, B., Murray, K. S., Larsen, D. S., & Brooker, S. (2007). Dicopper(II) complexes of a new pyrazolate-containing Schiff-base macrocycle and related acyclic ligand. Dalton Transactions, 467-475.

Journal - Research Article

Dyer, B. S., Jones, J. D., Ainge, G. D., Denis, M., Larsen, D. S., & Painter, G. F. (2007). Synthesis and structure of phosphatidylinositol dimannoside. Journal of Organic Chemistry, 72, 3282-3288.

Journal - Research Article

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