Lysine-based chiral vesicles

Guihua Li; Lei Feng; Peini Zhao; Wenlong Xu; Yanran Wang; Aixin Song; Jingcheng Hao

doi:10.1016/j.jcis.2014.05.069

Lysine-based chiral vesicles

J Colloid Interface Sci. 2014 Oct 1:431:233-40. doi: 10.1016/j.jcis.2014.05.069. Epub 2014 Jun 18.

Authors

Guihua Li¹, Lei Feng¹, Peini Zhao¹, Wenlong Xu¹, Yanran Wang¹, Aixin Song², Jingcheng Hao¹

Affiliations

¹ Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan 250100, China.
² Key Laboratory of Colloid and Interface Chemistry, Shandong University, Ministry of Education, Jinan 250100, China. Electronic address: songaixin@sdu.edu.cn.

PMID: 25016167
DOI: 10.1016/j.jcis.2014.05.069

Abstract

Uni-lamellar and multi-lamellar vesicles were prepared by the enantiomers of a biological molecule, L-lysine or D-lysine, with a double-tail weak monoacid, di-(2-ethylhexyl) phosphoric acid (abbreviated as DEHPA), in water. With the addition of DEHPA to lysine aqueous solutions, ion-pairs are formed through the acid-base reaction between the lysine cations and DEHP(-) anions. The self-assembled vesicles were proved to be driven by the hydrogen bonding between the side-chain amino groups in lysine molecules and the polar groups of DEHP(-) species. The combination of DEHPA and lysine through electrostatic interactions and hydrogen bonding reduces the cross-sectional area of the hydrophilic groups, improving the surface activity and inducing a microstructural transition from primitive aggregates to micelles, and to vesicles in solution. Due to the chirality of the lysine molecules, the aggregates exhibited diverse chiral properties along with the microstructural transitions.

Keywords: Aggregation behavior; Biological molecule; Chirality; Hydrogen bonding; Lysine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Lysine / chemistry*
Organophosphates / chemistry*

Substances

Organophosphates
di-2-(ethylhexyl)phosphoric acid
Lysine