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Dynamic covalent transport of amino acids across lipid bilayers

Dynamic covalent transport of amino acids across lipid bilayers
Dynamic covalent transport of amino acids across lipid bilayers
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.
0002-7863
1476-1484
Wu, Xin
65360fe8-d25a-4652-b7e4-40d513b57e7e
Busschaert, Nathalie
bf307f09-0a86-4a03-afd8-4b0a59a8f72b
Wells, Neil J.
86312185-007b-495b-86da-4e2e5b9b8025
Jiang, Yun-Bao
d7717409-7411-4027-97ce-218de4ff6b18
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Wu, Xin
65360fe8-d25a-4652-b7e4-40d513b57e7e
Busschaert, Nathalie
bf307f09-0a86-4a03-afd8-4b0a59a8f72b
Wells, Neil J.
86312185-007b-495b-86da-4e2e5b9b8025
Jiang, Yun-Bao
d7717409-7411-4027-97ce-218de4ff6b18
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

Wu, Xin, Busschaert, Nathalie, Wells, Neil J., Jiang, Yun-Bao and Gale, Philip A. (2015) Dynamic covalent transport of amino acids across lipid bilayers. Journal of the American Chemical Society, 137 (4), 1476-1484. (doi:10.1021/ja510063n).

Record type: Article

Abstract

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.

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Accepted/In Press date: 15 January 2015
e-pub ahead of print date: 27 January 2015
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 373782
URI: https://eprints.soton.ac.uk/id/eprint/373782
ISSN: 0002-7863
PURE UUID: 413da448-adbd-4147-8df4-58085be1bdf9
ORCID for Neil J. Wells: ORCID iD orcid.org/0000-0002-4607-5791
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

Catalogue record

Date deposited: 02 Feb 2015 10:28
Last modified: 20 Jul 2019 01:12

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Contributors

Author: Xin Wu
Author: Nathalie Busschaert
Author: Neil J. Wells ORCID iD
Author: Yun-Bao Jiang
Author: Philip A. Gale ORCID iD

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