Poster Presentation 24th Annual Lorne Proteomics Symposium 2019

Bespoke deuterated lipid molecules for structure function applications from the National Deuteration Facility  (#99)

Karyn L Wilde 1 , Nageshwar R Yepuri 1 , James K Howard 1 , Anwen M Krause-Heuer 1 , Peter J Holden 1 , Tamim A Darwish 1
  1. National Deuteration Facility - ANSTO, Lucas Heights, NSW, Australia

Deuterium (2H or D) is a naturally occurring stable isotope of hydrogen (1H or H) which contains a neutron in addition to the proton and electron found in the naturally abundant protium 1H. Molecular deuteration of molecules significantly increases the options in structure function investigations using MS, NMR, neutron scattering and other techniques but there have been limited global initiatives in the production and thus availability of complex deuterated small molecules such as lipids and fatty acids for such experiments.

Utilising catalysed 1H/2H exchange followed by custom chemical synthesis, the Chemical Deuteration laboratories of the National Deuteration Facility (NDF) of the Australian Nuclear Science and Technology Organisation are able to produce and supply relevant and bespoke deuterated compounds unavailable from commercial sources. We will describe the synthesis and application of new deuterated molecules with the NDF now able to produce deuterated cholesterol, head and/or tail deuterated lipids or selectively deuterated triglycerides,1 including phospholipids based on deuterated oleyl chains with a range of head groups. These include perdeuterated 1,2-oleoyl-sn-glycero-3-phosphocholine (POPC)2,  selectively deuterated POPC, branched chain (phytanic) phospholipids 1,2-diphytanoyl-sn-glycero-3-phosphocholine (DPhyPC)3, perdeuterated phytantriol4 and perdeuterated mono and di-oleoyl glycerol and phytanoyl monoethanolamide.5 These lipids have been extensively used in constructing biologically more relevant lipidic matrices for investigations using neutron, NMR, IR and MS techniques.

The National Deuteration Facility is partly supported by the National Collaborative Research Infrastructure Strategy – an initiative of the Australian Government.

  1. Salentinig, S.; Yepuri, N. R.; Hawley, A.; Boyd, B. J.; Gilbert, E.; Darwish, T. A. Chemistry and physics of lipids 2015, 190, 43.
  2. Yepuri, N. R.; Darwish, T. A.; Krause-Heuer, A. M.; Leung, A. E.; Delhom, R.; Wacklin, H. P.; Holden, P. J. ChemPlusChem 2016, 81, 315.
  3. Yepuri, N. R.; Holt, S. A.; Moraes, G.; Holden, P. J.; Hossain, K. R.; Valenzuela, S. M.; James, M.; Darwish, T. A. Chem. Phys. Lipids 2014, 183, 22.
  4. Yepuri, N. R.; Clulow, A. J.; Prentice, R. N.; Gilbert, E. P.; Hawley, A.; Rizwan, S. B.; Boyd, B. J.; Darwish, T. A. Journal of colloid and interface science 2018.
  5. van 't Hag, L.; de Campo, L.; Garvey, C. J.; Feast, G. C.; Leung, A. E.; Yepuri, N. R.; Knott, R.; Greaves, T. L.; Tran, N.; Gras, S. L.; Drummond, C. J.; Conn, C. E. J. Phys. Chem. Lett. 2016, 7, 2862.