Postdoctoral Fellow financed by the Swiss National Science Foundation (Project No. 200020-109065).
pH-Sensitive Vesicles Containing a Lipidic β-Amino Acid with Two Hydrophobic Chains
Article first published online: 18 JAN 2008
Copyright © 2008 Verlag Helvetica Chimica Acta AG, Zürich
Chemistry & Biodiversity
Volume 5, Issue 1, pages 16–30, January 2008
How to Cite
Capone, S., Walde, P., Seebach, D., Ishikawa, T. and Caputo, R. (2008), pH-Sensitive Vesicles Containing a Lipidic β-Amino Acid with Two Hydrophobic Chains. Chemistry & Biodiversity, 5: 16–30. doi: 10.1002/cbdv.200890006
- Issue published online: 18 JAN 2008
- Article first published online: 18 JAN 2008
- Manuscript Received: 20 NOV 2007
- Amino acids;
The lipidic β-amino acid 2-(aminomethyl)-2-pentadecylheptadecanoic acid (1) was synthesized via the alkylation of the C(α)-atom of fully protected β-alanine. Mixed large unilamellar vesicles with a diameter between 100 and 200 nm containing POPC (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) and 1 at a molar ratio of 9 : 1 were prepared and found to have a surface charge which is dependent on pH. At slightly acidic pH, the vesicles were positively charged, and at alkaline pH negatively charged. Dynamic light scattering, zeta potential, and cryo-transmission electron-microscopy measurements indicated that the mixed vesicles fused at pH 4–5 with negatively charged mixed vesicles composed of POPC and POPG (9.8 : 1, molar ratio), POPG being 1-palmitoyl-2-oleoyl-sn-glycero-3-[phospho-rac-(1-glycerol)].