title: Effect of phosphatidylcholine vesicle size on chirality induction and chiral discrimination.
abstract: The effect of the size of phosphatidylcholine (PC) vesicles on the induction of chirality and chiral discrimination was examined. Three kinds of vesicles formed with l-dimyristoyl, l-dipalmitoyl, or egg yolk PCs induced circular dichroisms (CDs) with the sign and intensity of the Cotton effect different from those of monomeric PCs. The CD intensity of the vesicles increased with a decrease in the vesicle size. Furthermore, the helicity of heterohelicene derivatives in a rapid equilibrium between right-handed (P) and left-handed (M) enantiomers was biased toward the M enantiomer side in l-PC vesicles, implying chiral discrimination by the vesicles. The extent of the bias toward the M enantiomer increased with an increase in vesicle size. Both the chirality induction and chiral discrimination were enhanced in a low-fluidity gel phase in comparison with those in a high-fluidity liquid-crystalline phase for every kind of vesicle of every size examined.
authors.affiliation: Faculty of Pharmaceutical Sciences, Josai University, Saitama, Japan. hnaka@josai.ac.jp
authors.forename: Hiroko
authors.initials: H
authors.lastname: Nakagawa
authors.forename: Mayumi
authors.initials: M
authors.lastname: Onoda
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Masuoka
authors.forename: Koh-Ichi
authors.initials: K
authors.lastname: Yamada
mesh_terms: D002942:Circular Dichroism; D007202:Indicators and Reagents; D008567:Membranes, Artificial; D010316:Particle Size; D010713:Phosphatidylcholines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D008567:Membranes, Artificial; D010713:Phosphatidylcholines