PhD, 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
Publications
Thwaite, S. H., Read, M. I., Larsen, D. S., Harrison, J. C., & Sammut, I. A. (2022, August-September). Prophylactic organic carbon monoxide donors protect hypertrophic hearts against ischaemia-reperfusion injury. Verbal presentation at the Australasian Society of Clinical & Experimental Pharmacologists & Toxicologists (ASCEPT) NZ Annual Scientific Meeting, Queenstown, New Zealand.
Bell, N. T., Payne, C. M., Sammut, I. A., & Larsen, D. S. (2022). Mechanistic studies of carbon monoxide release from norborn-2-en-7-one CORMs. Asian Journal of Organic Chemistry. Advance online publication. doi: 10.1002/ajoc.202200350
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
Bell, N. T., Payne, C. M., Sammut, I. A., & Larsen, D. S. (2022). Mechanistic studies of carbon monoxide release from norborn-2-en-7-one CORMs. Asian Journal of Organic Chemistry. Advance online publication. doi: 10.1002/ajoc.202200350
Journal - Research Article
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