Phase transfer of monosaccharides through noncovalent interactions: selective extraction of glucose by a lipophilic cage receptor

Proceedings of the National Academy of Sciences of the United States of America
Theo J RyanAnthony P. Davis

Abstract

We have previously shown that macrotricyclic host 1a is a powerful receptor for glucopyranosyl units in the nonpolar medium of chloroform. However, the solubility properties of 1a did not permit studies of the extraction of carbohydrates from aqueous solution. This paper describes the synthesis of the new variant 1b, furnished with a highly lipophilic exterior array of 12 benzyloxy substituents. In homogeneous solution, 1b behaves much as 1a, binding n-octyl beta-d-glucoside with K(a) = 720 M(-1) in CD(3)OH/CDCl(3) (8:92). In two-phase experiments, the improved solubility of 1b allows carbohydrate extraction to be observed. Three hexoses (glucose, galactose, and mannose), two pentoses (ribose and xylose), and the two methyl glucosides are all extracted substantially into chloroform from 1 M aqueous solutions. Among the hexoses, 1b shows notable affinity and selectivity for glucose, extracting detectable amounts even from 0.1 M aqueous solutions.

References

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Citations

Dec 23, 2004·Angewandte Chemie·Emmanuel KleinAnthony P Davis
Mar 18, 2011·The Journal of Organic Chemistry·Hajime AbeMasahiko Inouye
Sep 12, 2007·Chemical Communications : Chem Comm·Emmanuel KleinAnthony P Davis
Oct 27, 2007·Science·Yann FerrandAnthony P Davis
Jul 8, 2009·Cellular and Molecular Life Sciences : CMLS·D Barney WalkerAnthony P Davis
Dec 18, 2013·Chemical Society Reviews·Gang Zhang, Michael Mastalerz
Aug 3, 2018·Chemistry : a European Journal·Kalanidhi PalanichamyAdam B Braunschweig
Jul 19, 2006·Chemistry : a European Journal·Minoru WakiMasahiko Inouye
Sep 21, 2006·Angewandte Chemie·Oscar FrancesconiStefano Roelens
May 8, 2009·Organic & Biomolecular Chemistry·Monika Mazik, Arno C Buthe
Aug 27, 2009·Organic & Biomolecular Chemistry·Anthony P Davis
Jun 24, 2010·Angewandte Chemie·Michael Mastalerz
Mar 20, 2020·Chemical Society Reviews·Anthony P Davis
Oct 14, 2004·The Biochemical Journal·Edwin J A VeldhuizenLindsay D Eltis
Jun 17, 2020·Angewandte Chemie·Valentina AbetAnna G Slater
Jun 22, 2012·Organic & Biomolecular Chemistry·Gururaj Joshi, Anthony P Davis
Apr 8, 2020·Chemistry : a European Journal·M Fernando BravoAdam B Braunschweig
Oct 24, 2020·Biochemistry·M Fernando BravoAdam B Braunschweig
Jul 30, 2008·Journal of the American Chemical Society·Joakim AndréassonDevens Gust
Nov 16, 2019·Journal of the American Chemical Society·Dawei ZhangJonathan R Nitschke
Sep 11, 2021·Journal of the American Chemical Society·Wenqi LiuJ Fraser Stoddart

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