title: Cucurbit[7]uril: a high-affinity host for encapsulation of amino saccharides and supramolecular stabilization of their α-anomers in water.
abstract: Cucurbit[7]uril (CB[7]), an uncharged and water-soluble macrocyclic host, binds protonated amino saccharides (D-glucosamine, D-galactosamine, D-mannosamine and 6-amino-6-deoxy-D-glucose) with excellent affinity (Ka =10(3) to 10(4)  M(-1) ). The host-guest complexation was confirmed by NMR spectroscopy, isothermal titration calorimetry (ITC), and MALDI-TOF mass spectral analyses. NMR analyses revealed that the amino saccharides, except D-mannosamine, are bound as α-anomers within the CB[7] cavity. ITC analyses reveal that CB[7] has excellent affinity for binding amino saccharides in water. The maximum affinity was observed for D-galactosamine hydrochloride (Ka =1.6×10(4)  M(-1) ). Such a strong affinity for any saccharide in water using a synthetic receptor is unprecedented, as is the supramolecular stabilization of an α-anomer by the host.
authors: Center for Self-assembly and Complexity (CSC), Institute for Basic Science (IBS), Pohang, 790-784 (Republic of Korea); Department of Chemistry, and Division of Advanced Materials Science, Pohang University of Science and Technology, Pohang, 790-784 (Republic of Korea) http://csc.ibs.re.kr/
authors: Yoonjung
authors: Y
authors: Jang
authors: Ramalingam
authors: R
authors: Natarajan
authors: Young Ho
authors: YH
authors: Ko
authors: Kimoon
authors: K
authors: Kim
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D046911:Macromolecular Substances / Q000737:chemistry; D008968:Molecular Conformation; D014867:Water / Q000737:chemistry; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
chemical_list: D001952:Bridged-Ring Compounds; D002241:Carbohydrates; D007093:Imidazoles; D046911:Macromolecular Substances; D014867:Water; C456276:cucurbit(7)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
keywords: NMR spectroscopy; calorimetry; host-guest systems; hydrophobic effect; molecular recognition