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• W1992654987 abstract "To develop an efficient sugar extractant on the basis of the mechanistic view a phenylboronic acid bearing a trioctylammonium group at the ortho position (4) was synthesized. To avoid the complexity we employed a simple two-phase solvent-extraction system which corresponds to the first step in membrane transport, i.e., extraction from a donating aqueous phase to an organic liquid membrane phase. The extraction rates and equilibria were estimated using α-p-nitrophenyl-D-glucopyranoside as a sugar and 1,2-dichloroethane as an organic phase and compared with those of a 2-methylphenylboronic acid (5) / trioctylmethylammonium chloride (TOMAC) 1:1 binary system. The extraction rates for 4 were faster by 2.5 – 29 fold than those for 5 + TOMAC. The distribution coefficients were also enhanced by 5 – 8 fold. The results indicate that the intramolecular quaternary ammonium group is very effective to neutralize the anionic charge developed in the boron atom upon sugar-binding and create extractable zwitterionic sugar complexes." @default.
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• W1992654987 date "1996-09-01" @default.
• W1992654987 modified "2023-09-23" @default.
• W1992654987 title "Efficient glucoside extraction mediated by a boronic acid with an intramolecular quaternary ammonium ion" @default.
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• W1992654987 doi "https://doi.org/10.1016/0040-4020(96)00770-3" @default.
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