Chiral Recognition of l -Amino Acids on Liposomes Prepared with l -Phospholipid

Takaaki Ishigami; Keishi Suga; Hiroshi Umakoshi

doi:10.1021/acsami.5b07198

Chiral Recognition of l -Amino Acids on Liposomes Prepared with l -Phospholipid

Takaaki Ishigami, Keishi Suga, Hiroshi Umakoshi

ENG - Chemical Engineering

Osaka University

Research output: Contribution to journal › Article › peer-review

66 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	21065-21072
Number of pages	8
Journal	ACS applied materials & interfaces
Volume	7
Issue number	38
DOIs	https://doi.org/10.1021/acsami.5b07198
Publication status	Published - 2015 Sept 30

Keywords

adsorption
amino acids
chiral recognition
electrostatic interaction
hydrogen bond
liposomes
lock-and-key model

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10.1021/acsami.5b07198

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title = "Chiral Recognition of l -Amino Acids on Liposomes Prepared with l -Phospholipid",

abstract = "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.",

keywords = "adsorption, amino acids, chiral recognition, electrostatic interaction, hydrogen bond, liposomes, lock-and-key model",

author = "Takaaki Ishigami and Keishi Suga and Hiroshi Umakoshi",

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T1 - Chiral Recognition of l -Amino Acids on Liposomes Prepared with l -Phospholipid

AU - Ishigami, Takaaki

AU - Suga, Keishi

AU - Umakoshi, Hiroshi

PY - 2015/9/30

Y1 - 2015/9/30

N2 - 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.

AB - 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.

KW - adsorption

KW - amino acids

KW - chiral recognition

KW - electrostatic interaction

KW - hydrogen bond

KW - liposomes

KW - lock-and-key model

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DO - 10.1021/acsami.5b07198

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SN - 1944-8244

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EP - 21072

JO - ACS applied materials & interfaces

JF - ACS applied materials & interfaces

IS - 38

ER -

Chiral Recognition of l -Amino Acids on Liposomes Prepared with l -Phospholipid

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Keywords

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