Literature DB >> 26339952

Chiral Recognition of L-Amino Acids on Liposomes Prepared with L-Phospholipid.

Takaaki Ishigami1, Keishi Suga1, Hiroshi Umakoshi1.   

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.

Entities:  

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

Mesh:

Substances:

Year:  2015        PMID: 26339952     DOI: 10.1021/acsami.5b07198

Source DB:  PubMed          Journal:  ACS Appl Mater Interfaces        ISSN: 1944-8244            Impact factor:   9.229


  8 in total

1.  Chirality-Driven Transportation and Oxidation Prevention by Chiral Selenium Nanoparticles.

Authors:  Yanyu Huang; Yuanting Fu; Mengting Li; Dawei Jiang; Christopher J Kutyreff; Jonathan W Engle; Xiaoli Lan; Weibo Cai; Tianfeng Chen
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-23       Impact factor: 15.336

2.  Stereoselectivity of Interaction of Nonsteroidal Anti-Inflammatory Drug S-Ketoprofen with L/D-Tryptophan in Phospholipid Membranes.

Authors:  Anna V Mastova; Olga Yu Selyutina; Nikolay E Polyakov
Journal:  Membranes (Basel)       Date:  2022-04-24

3.  Discrimination of Stereoisomers by Their Enantioselective Interactions with Chiral Cholesterol-Containing Membranes.

Authors:  Hironori Tsuchiya; Maki Mizogami
Journal:  Molecules       Date:  2017-12-25       Impact factor: 4.411

4.  Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers.

Authors:  Francis G A Lister; Natasha Eccles; Sarah J Pike; Robert A Brown; George F S Whitehead; James Raftery; Simon J Webb; Jonathan Clayden
Journal:  Chem Sci       Date:  2018-07-17       Impact factor: 9.825

5.  Enantioselective C-C Bond Formation Enhanced by Self-Assembly of Achiral Surfactants.

Authors:  Fumihiko Iwasaki; Keishi Suga; Yukihiro Okamoto; Hiroshi Umakoshi
Journal:  ACS Omega       Date:  2017-04-12

6.  Chirality-Dependent Adsorption between Amphipathic Peptide and POPC Membrane.

Authors:  Ke Chen; Yuebiao Sheng; Jun Wang; Wei Wang
Journal:  Int J Mol Sci       Date:  2019-09-25       Impact factor: 5.923

7.  Chiral lipid bilayers are enantioselectively permeable.

Authors:  Juan Hu; Wesley G Cochrane; Alexander X Jones; Donna G Blackmond; Brian M Paegel
Journal:  Nat Chem       Date:  2021-06-10       Impact factor: 24.427

Review 8.  Chiral nanomaterials for tumor therapy: autophagy, apoptosis, and photothermal ablation.

Authors:  Zaihui Peng; Long Yuan; Juncheng XuHong; Hao Tian; Yi Zhang; Jun Deng; Xiaowei Qi
Journal:  J Nanobiotechnology       Date:  2021-07-22       Impact factor: 10.435

  8 in total

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