Chiral Recognition of L-Amino Acids on Liposomes Prepared with L-Phospholipid.
In this study, we demonstrated that liposomes composed of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) can recognize several l-amino acids, but not their d-enantiomers, by analyzing their adsorptive behavior and using circular dichroism spectroscopy. Changes in liposomal membrane properties, determined based on fluorescent probe analysis and differential scanning calorimetry, were induced by l-amino acid binding. UV resonance Raman spectroscopy analysis suggested that the chiral recognition was mediated by electrostatic, hydrophobic, and hydrogen bond interactions, where the recognition site could therefore be constructed on the DPPC membrane. Our findings clearly indicate the potential function of liposomes in asymmetric recognition.
Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University , 1-3 Machikaneyamacho, Toyonaka, Osaka 560-8531, Japan.
Takaaki
T
Ishigami
Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University , 1-3 Machikaneyamacho, Toyonaka, Osaka 560-8531, Japan.
Keishi
K
Suga
Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University , 1-3 Machikaneyamacho, Toyonaka, Osaka 560-8531, Japan.
Hiroshi
H
Umakoshi
D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry; D000327:Adsorption; D000596:Amino Acids / Q000737:chemistry*; D002152:Calorimetry, Differential Scanning; D002942:Circular Dichroism; D008081:Liposomes / Q000737:chemistry*; D008567:Membranes, Artificial; D008968:Molecular Conformation; D010743:Phospholipids / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013059:Spectrum Analysis, Raman; D013696:Temperature; D013997:Time Factors
D000596:Amino Acids; D008081:Liposomes; D008567:Membranes, Artificial; D010743:Phospholipids; D015060:1,2-Dipalmitoylphosphatidylcholine
adsorption; amino acids; chiral recognition; electrostatic interaction; hydrogen bond; liposomes; lock-and-key model