A folding decalin tetra-urea for transmembrane anion transport

Hennie Valkenier; Christopher M. Dias; Craig P. Butts; Anthony P. Davis

doi:10.1016/j.tet.2017.04.064

A folding decalin tetra-urea for transmembrane anion transport

Hennie Valkenier, Christopher M. Dias, Craig P. Butts, Anthony P. Davis

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

A new approach to anionophore design combines a trans-decalin scaffold with flexible o-phenylene bis-urea side-arms. The scaffold preorganises the side-arms, which can fold to encompass anionic substrates. A prototype has been synthesised by coupling an o-aminophenyl urea to a decalin bis-isocyanate, and has been shown to be active for anion binding and transport. Modelling and NMR studies show that the unbound receptor is capable of intramolecular hydrogen bonding but can reorganise to form up to eight hydrogen bonds to a chloride anion.

Original language	English
Pages (from-to)	4955-4962
Number of pages	8
Journal	Tetrahedron
Volume	73
Issue number	33
Early online date	2 May 2017
DOIs	https://doi.org/10.1016/j.tet.2017.04.064
Publication status	Published - 17 Aug 2017

Structured keywords

BCS and TECS CDTs

Keywords

Supramolecular chemistry
Anion binding
Anion transport
Host-guest systems
Urea
Foldamer

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10.1016/j.tet.2017.04.064

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Elsevier at http://www.sciencedirect.com/science/article/pii/S0040402017304659. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 961 KBLicence: CC BY-NC-ND
Supplementary information PDF
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Elsevier at http://www.sciencedirect.com/science/article/pii/S0040402017304659. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 1.81 MBLicence: CC BY-NC-ND

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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P.
28/02/14 → 29/11/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research
Synthetic Anionophores with Therapeutic Potential - a Coordinated Two-Centre Approach
Davis, A. P.
10/09/12 → 9/03/16
Project: Research

Cite this

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title = "A folding decalin tetra-urea for transmembrane anion transport",

abstract = "A new approach to anionophore design combines a trans-decalin scaffold with flexible o-phenylene bis-urea side-arms. The scaffold preorganises the side-arms, which can fold to encompass anionic substrates. A prototype has been synthesised by coupling an o-aminophenyl urea to a decalin bis-isocyanate, and has been shown to be active for anion binding and transport. Modelling and NMR studies show that the unbound receptor is capable of intramolecular hydrogen bonding but can reorganise to form up to eight hydrogen bonds to a chloride anion.",

keywords = "Supramolecular chemistry, Anion binding, Anion transport, Host-guest systems, Urea, Foldamer",

author = "Hennie Valkenier and Dias, {Christopher M.} and Butts, {Craig P.} and Davis, {Anthony P.}",

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language = "English",

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pages = "4955--4962",

journal = "Tetrahedron",

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T1 - A folding decalin tetra-urea for transmembrane anion transport

AU - Valkenier, Hennie

AU - Dias, Christopher M.

AU - Butts, Craig P.

AU - Davis, Anthony P.

PY - 2017/8/17

Y1 - 2017/8/17

N2 - A new approach to anionophore design combines a trans-decalin scaffold with flexible o-phenylene bis-urea side-arms. The scaffold preorganises the side-arms, which can fold to encompass anionic substrates. A prototype has been synthesised by coupling an o-aminophenyl urea to a decalin bis-isocyanate, and has been shown to be active for anion binding and transport. Modelling and NMR studies show that the unbound receptor is capable of intramolecular hydrogen bonding but can reorganise to form up to eight hydrogen bonds to a chloride anion.

AB - A new approach to anionophore design combines a trans-decalin scaffold with flexible o-phenylene bis-urea side-arms. The scaffold preorganises the side-arms, which can fold to encompass anionic substrates. A prototype has been synthesised by coupling an o-aminophenyl urea to a decalin bis-isocyanate, and has been shown to be active for anion binding and transport. Modelling and NMR studies show that the unbound receptor is capable of intramolecular hydrogen bonding but can reorganise to form up to eight hydrogen bonds to a chloride anion.

KW - Supramolecular chemistry

KW - Anion binding

KW - Anion transport

KW - Host-guest systems

KW - Urea

KW - Foldamer

U2 - 10.1016/j.tet.2017.04.064

DO - 10.1016/j.tet.2017.04.064

M3 - Article (Academic Journal)

SN - 0040-4020

VL - 73

SP - 4955

EP - 4962

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

A folding decalin tetra-urea for transmembrane anion transport

Abstract

Structured keywords

Keywords

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Projects

A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Synthetic Anionophores with Therapeutic Potential - a Coordinated Two-Centre Approach

Cite this