PMID: 11312968Apr 21, 2001Paper

Carbohydrate-based receptors with multiple thiourea binding sites. Multipoint hydrogen bond recognition of dicarboxylates and monosaccharides

The Journal of Organic Chemistry
Juan M BenitoJosé M García Fernandez

Abstract

The binding properties of multitopic sugar thiourea receptors toward dicarboxylate and monosaccharide guests have been examined taking glutarate and octyl beta-D-glucopyranoside as model ligands. For the anionic hydrogen bond acceptor, both the complex stoichiometry and the association constants (K(as)) were found to be strongly dependent on the relative disposition of recognition elements in the host. In contrast, for the glucoside guest a 1:1 stoichiometry was observed in all cases, the K(as) values being largely independent of the unbound state provided that geometrically equivalent supramolecular topologies can be achieved.

References

Jan 29, 2000·Current Opinion in Chemical Biology·T S Snowden, E V Anslyn
Jul 21, 2000·Carbohydrate Research·V M Díaz PérezJ M García Fernández
Aug 12, 2000·Chemistry : a European Journal·B R LintonA D Hamilton
Oct 24, 2001·The Journal of Organic Chemistry·Ramon Alibés, David R. Bundle

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Citations

Oct 19, 2007·Organic & Biomolecular Chemistry·Zhi-hua LinJing-ping Qu
Dec 10, 2009·Chemistry : a European Journal·Ana ArdáStefano Roelens
May 26, 2011·Chemistry : a European Journal·Vaishali VajpayeeKi-Whan Chi
May 12, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Amira MbarekJeanne Leblond Chain
Dec 20, 2011·Organic & Biomolecular Chemistry·M Belén JiménezM Cruz Caballero
Feb 20, 2007·Chemical Communications : Chem Comm·David Rodríguez-LucenaJosé M García Fernández
Aug 21, 2003·Organic & Biomolecular Chemistry·Francesco SansoneRocco Ungaro
Jan 27, 2015·Chembiochem : a European Journal of Chemical Biology·Caitlin E Miron, Anne Petitjean
Nov 26, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Anurag MishraKi-Whan Chi
Jan 23, 2004·Chemical Communications : Chem Comm·José L Jiménez BlancoJosé M García Fernández
Aug 30, 2008·Journal of the American Chemical Society·Lijun TangKwan Mook Kim
Dec 8, 2007·Bioconjugate Chemistry·Jeanne LeblondJean Herscovici
Dec 22, 2007·Chemical Reviews·Guy A HemburyYoshihisa Inoue
Apr 8, 2006·The Journal of Physical Chemistry. a·Vyacheslav S Bryantsev, Benjamin P Hay

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