Manifesting Subtle Differences of Neutral Hydrophilic Guest Isomers in a Molecular Container by Phase Transfer

  • Lee, Hyun Hee L.; 
  • Lee, Jong Wha; 
  • Jang, Yoonjung; 
  • Ko, Young Ho; 
  • Kim, Kimoon; 
  • ... Kim, Hugh I.
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초록

Achieving strong host-guest interactions between synthetic hosts and hydrophilic guests in solution is challenging because solvation effects overwhelm other effects. To resolve this issue, we transferred complexes of cucurbit[7]uril (CB[7]) and monosaccharides to the gas phase and report here their intrinsic host-guest chemistry in the absence of solvation effects. It was observed that effective host-guest interactions in the gas phase mediated by ammonium cations allow the differentiation of the monosaccharide isomers in complex with CB[7] upon vibrational excitation. The potential of the unique observation was extended to a quantitative supramolecular analytical method for the monosaccharide guests. The combination of host-guest chemistry and phase transfer presented in this study is an effective approach to overcome current limitations in supramolecular chemistry.

키워드

cucurbit[7]uril; gas-phase chemistry; host-guest systems; mass spectrometry; monosaccharides; IONIZATION MASS-SPECTROMETRY; HIGH-AFFINITY BINDING; GAS-PHASE; SUPRAMOLECULAR CHEMISTRY; COLLISIONAL ACTIVATION; NONCOVALENT COMPLEXES; GLUCOSE BIOSENSORS; RECOGNITION; HOST; AMINO
제목
Manifesting Subtle Differences of Neutral Hydrophilic Guest Isomers in a Molecular Container by Phase Transfer
저자
Lee, Hyun Hee L.; Lee, Jong Wha; Jang, Yoonjung; Ko, Young Ho; Kim, Kimoon; Kim, Hugh I.
DOI
10.1002/anie.201601320
발행일
2016-07-11
유형
Article
저널명
Angewandte Chemie International Edition
권
55
호
29
페이지
8249 ~ 8253