Dynamic Covalent Transport of Amino Acids across Lipid Bilayers
Autor: | Yun-Bao Jiang, Philip A. Gale, Nathalie Busschaert, Xin Wu, Neil J. Wells |
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Rok vydání: | 2015 |
Předmět: |
chemistry.chemical_classification
Aldehydes Osmosis Sulfonamides Magnetic Resonance Spectroscopy Sarcosine Stereochemistry Lipid Bilayers Imine Glycine Squaramide Biological Transport General Chemistry Membrane transport Biochemistry Catalysis Amino acid Kinetics chemistry.chemical_compound Colloid and Surface Chemistry chemistry Covalent bond Hemiaminal Lipid bilayer Cyclobutanes |
Zdroj: | Journal of the American Chemical Society. 137:1476-1484 |
ISSN: | 1520-5126 0002-7863 |
DOI: | 10.1021/ja510063n |
Popis: | We report a dynamic covalent approach to transmembrane transport of amino acids by the formation of a three-component assembly. A mixture of a squaramide and a lipophilic and electrophilic aldehyde is shown to synergistically transport highly polar glycine (Gly) across vesicle membranes. The transport was investigated by a 13C NMR assay, an osmotic response assay and a newly-developed fluorescence assay suitable for measuring Gly influx, and other fluorescence assays for leakage and pH change. The transport is proposed to occur via a hydrogen-bonded anionic glycine hemiaminal/imine, accompanied by transport of OH- in the opposite direction. Several control experiments support the role of hemiaminal/imine in the observed facilitated Gly transport. Proton NMR studies of a biphasic system show the presence of both the hemiaminal and imine formed between Gly and an aldehyde. Interestingly, the synergistic effect has also been observed for sarcosine (Sar) that can form hemiaminals but not imines. The results demonstrate the potential of hemiaminal formation for the facilitated transport of substrates containing primary and secondary amino groups. |
Databáze: | OpenAIRE |
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