Investigating the Influence of Steric Hindrance on Selective Anion Transport

Investigating the Influence of Steric Hindrance on Selective Anion Transport

A series of symmetrical and unsymmetrical alkyl tren based tris-thiourea anion transporters were synthesised and their anion binding and transport properties studied. Overall, increasing the steric bulk of the substituents resulted in improved chloride binding and transport abilities. Including a ma...

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Main Authors: Laura A. Jowett, Angela Ricci, Xin Wu, Ethan N. W. Howe, Philip A. Gale
Format: Article
Language:English
Published: MDPI AG 2019-04-01
Series:Molecules
Subjects:
anion transport
thioureas
lipid bilayer
Online Access:https://www.mdpi.com/1420-3049/24/7/1278
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spelling doaj-c88307a4bb6e41d3bb03aab651d91fdc2020-11-25T00:50:03ZengMDPI AGMolecules1420-30492019-04-01247127810.3390/molecules24071278molecules24071278Investigating the Influence of Steric Hindrance on Selective Anion TransportLaura A. Jowett0Angela Ricci1Xin Wu2Ethan N. W. Howe3Philip A. Gale4School of Chemistry (F11), The University of Sydney, Sydney, NSW 2006, AustraliaChemistry, University of Southampton, Southampton SO17 1BJ, UKSchool of Chemistry (F11), The University of Sydney, Sydney, NSW 2006, AustraliaSchool of Chemistry (F11), The University of Sydney, Sydney, NSW 2006, AustraliaSchool of Chemistry (F11), The University of Sydney, Sydney, NSW 2006, AustraliaA series of symmetrical and unsymmetrical alkyl tren based tris-thiourea anion transporters were synthesised and their anion binding and transport properties studied. Overall, increasing the steric bulk of the substituents resulted in improved chloride binding and transport abilities. Including a macrocycle in the scaffold enhanced the selectivity of chloride transport in the presence of fatty acids, by reducing the undesired H<sup>+</sup> flux facilitated by fatty acid flip-flop. This study demonstrates the benefit of including enforced steric hindrance and encapsulation in the design of more selective anion receptors.https://www.mdpi.com/1420-3049/24/7/1278anion transportthioureaslipid bilayer
collection DOAJ
language English
format Article
sources DOAJ
author Laura A. Jowett
Angela Ricci
Xin Wu
Ethan N. W. Howe
Philip A. Gale
spellingShingle Laura A. Jowett
Angela Ricci
Xin Wu
Ethan N. W. Howe
Philip A. Gale
Investigating the Influence of Steric Hindrance on Selective Anion Transport
Molecules
anion transport
thioureas
lipid bilayer
author_facet Laura A. Jowett
Angela Ricci
Xin Wu
Ethan N. W. Howe
Philip A. Gale
author_sort Laura A. Jowett
title Investigating the Influence of Steric Hindrance on Selective Anion Transport
title_short Investigating the Influence of Steric Hindrance on Selective Anion Transport
title_full Investigating the Influence of Steric Hindrance on Selective Anion Transport
title_fullStr Investigating the Influence of Steric Hindrance on Selective Anion Transport
title_full_unstemmed Investigating the Influence of Steric Hindrance on Selective Anion Transport
title_sort investigating the influence of steric hindrance on selective anion transport
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-04-01
description A series of symmetrical and unsymmetrical alkyl tren based tris-thiourea anion transporters were synthesised and their anion binding and transport properties studied. Overall, increasing the steric bulk of the substituents resulted in improved chloride binding and transport abilities. Including a macrocycle in the scaffold enhanced the selectivity of chloride transport in the presence of fatty acids, by reducing the undesired H<sup>+</sup> flux facilitated by fatty acid flip-flop. This study demonstrates the benefit of including enforced steric hindrance and encapsulation in the design of more selective anion receptors.
topic anion transport
thioureas
lipid bilayer
url https://www.mdpi.com/1420-3049/24/7/1278
work_keys_str_mv AT lauraajowett investigatingtheinfluenceofsterichindranceonselectiveaniontransport
AT angelaricci investigatingtheinfluenceofsterichindranceonselectiveaniontransport
AT xinwu investigatingtheinfluenceofsterichindranceonselectiveaniontransport
AT ethannwhowe investigatingtheinfluenceofsterichindranceonselectiveaniontransport
AT philipagale investigatingtheinfluenceofsterichindranceonselectiveaniontransport
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