Stereoselective synthesis of perdeuterated phytanic acid, its phospholipid derivatives and their formation into lipid model membranes for neutron reflectivity studies

Simple item page
dc.contributor.authorYepuri, NRen_AU
dc.contributor.authorHolt, SAen_AU
dc.contributor.authorMoraes, Gen_AU
dc.contributor.authorHolden, PJen_AU
dc.contributor.authorHossain, KRen_AU
dc.contributor.authorValenzuela, SMen_AU
dc.contributor.authorDarwish, TAen_AU
dc.contributor.authorJames, Men_AU
dc.date.accessioned2016-10-31T04:23:46Zen_AU
dc.date.available2016-10-31T04:23:46Zen_AU
dc.date.issued2014-10-01en_AU
dc.date.statistics2016-10-31en_AU
dc.description.abstractWe describe a straightforward method, for synthesis of large scale (gram quantities) of highly deuterated phytanic acid from commercially available phytol while preserving the stereochemistry around the chiral centres. The subsequent synthesis of tail-deuterated analogues of the archeabacterial membrane lipids 1,2-di(3RS,7R,11R-phytanyl)-sn-glycero-3-phosphocholine (DPEPC) and 1,2-di(3RS,7R,11R-phytanoyl)-sn-glycero-3-phosphocholine (DPhyPC) from perdeuterated phytanic acid is also described. Both lipids were employed in construction of two different model membranes, namely Langmuir monolayers and a tethered bilayer membrane (TBM) on a solid substrate, characterised by pressure area isotherm and neutron reflectometry techniques. At 10 mN/m pressure the head-group thickness of both monolayers was similar while the thickness of the tail region was significantly larger for tail-deuterated DPhyPC, which was evident from a smaller area per molecule. At 20 mN/m the thickness of the head and tail regions in both lipids was comparable, yet the area per molecule of tail-deuterated DPhyPC was 10% smaller than tail-deuterated DPEPC. In the TBM bilayer model membrane, the thickness of the lipid tails in both inner and outer leaflets was 8.2 Å, giving a total of 16.4 Å. Deuteration enabled unambiguous determination of the relative proportion of the hydrogenous tether, phospholipid and subphase. © 2014, Elsevier Ireland Ltd.en_AU
dc.identifier.citationYepuri, N. R., Holt, S. A., Moraes, G., Holden, P. J., Hossain, K. R., Valenzuela, S. M., James, M., & Darwish, T. A. (2014). Stereoselective synthesis of perdeuterated phytanic acid, its phospholipid derivatives and their formation into lipid model membranes for neutron reflectivity studies. Chemistry and Physics of Lipids, 183, 22-33. doi:10.1016/j.chemphyslip.2014.04.004en_AU
dc.identifier.govdoc7548en_AU
dc.identifier.issn0009-3084en_AU
dc.identifier.journaltitleChemistry and Physics of Lipidsen_AU
dc.identifier.pagination22-33en_AU
dc.identifier.urihttp://dx.doi.org/10.1016/j.chemphyslip.2014.04.004en_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/7984en_AU
dc.identifier.volume183en_AU
dc.language.isoenen_AU
dc.publisherElsevieren_AU
dc.subjectDeuterationen_AU
dc.subjectLipidsen_AU
dc.subjectMembranesen_AU
dc.subjectSynthesisen_AU
dc.subjectStereochemistryen_AU
dc.titleStereoselective synthesis of perdeuterated phytanic acid, its phospholipid derivatives and their formation into lipid model membranes for neutron reflectivity studiesen_AU
dc.typeJournal Articleen_AU
Files
License bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
license.txt
Size:
1.71 KB
Format:
Item-specific license agreed upon to submission
Description:
Download
Collections
Journal Articles