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Sugar-sensitive supramolecular structures based on phenylboronic Acid-modified cyclodextrins.

Kiminobu Nakamura1, Tomohiro Seki, Yuya Egawa

  • 1Faculty of Pharmaceutical Sciences, Josai University.

Chemical & Pharmaceutical Bulletin
|August 23, 2013
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Phenylboronic acid-modified cyclodextrins form distinct supramolecular structures. These structures, including polymers and dimers, can be disassembled by sugars through boronate interactions.

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High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
14:37

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

Published on: July 6, 2012

Area of Science:

  • Supramolecular Chemistry
  • Materials Science

Background:

  • Cyclodextrins (CyDs) are cyclic oligosaccharides with a hydrophobic cavity and hydrophilic exterior, widely used in host-guest chemistry.
  • Phenylboronic acid (PBA) derivatives are known to form reversible covalent bonds with diols, such as those found in saccharides.

Purpose of the Study:

  • To develop and characterize supramolecular structures from phenylboronic acid-modified cyclodextrins (PBA-CyDs).
  • To investigate the intermolecular interactions within these supramolecular assemblies.
  • To explore the stimuli-responsive behavior of PBA-CyD structures towards saccharides.

Main Methods:

  • Synthesis of phenylboronic acid-modified cyclodextrins (PBA-α-CyD and PBA-β-CyD).
  • Characterization of supramolecular structures using two-dimensional Nuclear Magnetic Resonance (2D-NMR) spectroscopy.
  • Powder X-ray diffraction (PXRD) analysis to determine structural arrangements.
  • Investigation of structural disassembly in the presence of various sugars.

Main Results:

  • PBA-α-CyD self-assembled into a head-to-tail supramolecular polymer.
  • PBA-β-CyD formed a head-to-head dimer.
  • Intermolecular interactions between the PBA moiety and the cyclodextrin cavity were confirmed.
  • The supramolecular structures were effectively disintegrated upon addition of sugars, attributed to boronate-sugar interactions.

Conclusions:

  • Phenylboronic acid modification enables the formation of well-defined supramolecular structures with cyclodextrins.
  • The type of cyclodextrin (α- or β-) dictates the resulting supramolecular architecture.
  • These PBA-CyD supramolecular systems exhibit stimuli-responsive disassembly in the presence of sugars, highlighting their potential for sensing or drug delivery applications.