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Diaxial diureido decalins as compact, efficient, and tunable anion transporters.

Journal of the American Chemical Society (2011-01-25)
Sabir Hussain, Peter R Brotherhood, Luke W Judd, Anthony P Davis
ABSTRACT

Decalins bearing two axial -NHCONHAr substituents and an ester-linked alkyl side chain have been synthesized and studied as anion receptors and transporters. The design relates to steroid-based "cholapods" but is more compact and less intrinsically lipophilic. Transport rates depend on both NHAr and the alkyl side chain. High activities can be achieved; with optimal substitution, chloride-nitrate exchange across vesicle membranes is measurable at transporter/lipid ratios as low as 1:250,000.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, anhydrous, ≥99%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, reagent grade, 98%
Sigma-Aldrich
cis-Decahydronaphthalene, 99%
Sigma-Aldrich
trans-Decahydronaphthalene, 99%

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