title: Condensation properties of vesicles formed from an amphiphilic N-phosphorylamino acid.
abstract: Stable unilamellar vesicles were formed in water under appropriate pH from dispersions of N-(O,O-di-n-hexadecyl)phosphorylalanine, an amphiphilic N-phosphorylamino acid. We found that condensation occurred in the vesicle solution after incubated at 40 degrees C, which may contribute to the stability of the vesicular system. Dipeptide derivative in the vesicle solution was identified by electrospray ionization mass spectrometry (ESI-MS), which suggests the peptide formation without any coupling reagents. Hydrogen bond and electrostatic interactions play important roles in the process of vesicle formation, while the suitable orientation and packing of the amphiphilic molecules at the vesicle/water interface together with certain conformational freedom in the vesicular bilayer are considered to be most favorable for the condensation in ordered systems as vesicles.
authors.affiliation: Key Lab of Bioorganic Phosphorus Chemistry and Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China.
authors.forename: Hai-Yan
authors.initials: HY
authors.lastname: Wang
authors.forename: Yan-Mei
authors.initials: YM
authors.lastname: Li
authors.forename: Yi
authors.initials: Y
authors.lastname: Xiao
authors.forename: Yu-Fen
authors.initials: YF
authors.lastname: Zhao
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008954:Models, Biological; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013499:Surface Properties; D013501:Surface-Active Agents / Q000737:chemistry*; D022161:Transport Vesicles / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: C514454:N-(O,O-di-n-hexadecyl)phosphorylalanine; D010455:Peptides; D013501:Surface-Active Agents; D014867:Water; D000409:Alanine