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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Structure-Reactivity Relationships in Boronic Acid-Diol Complexation.

William L A Brooks1, Christopher C Deng1, Brent S Sumerlin1

  • 1George & Josephine Butler Polymer Research Laboratory, Center for Macromolecular Science & Engineering, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.

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Understanding boronic acid structure-reactivity is key for biomaterials. This study reveals how boronic acid design and pH affect binding to sugars and polyols, guiding future applications.

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Area of Science:

  • Biomaterials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Boronic acids are crucial in biomaterials for binding diols like saccharides.
  • Existing boronic acid structures lack clear structure-reactivity relationship understanding for diol binding.
  • Developing responsive hydrogels requires precise control over boronic acid-diol interactions.

Purpose of the Study:

  • To investigate structure-reactivity relationships in boronic acids for diol binding.
  • To determine pKa and binding constants of various organoboron compounds with biologically relevant diols.
  • To provide guidance for selecting organoboron compounds in materials chemistry.

Main Methods:

  • Spectroscopic titration to determine boronic acid pKa values.
  • Fluorescence spectroscopy with competitive binding studies to ascertain binding constants.
  • Systematic variation of boronic acid electronics and sterics.

Main Results:

  • Established key structure-reactivity relationships for boronic acid-diol interactions.
  • Demonstrated the critical influence of both boronic acid structure and solution pH on binding affinity.
  • Quantified binding constants for sorbitol, fructose, and glucose with diverse boronic acids.

Conclusions:

  • Boronic acid structure and pH are critical factors for effective diol binding.
  • This research provides essential data for optimizing boronic acid selection in sensing and delivery systems.
  • Findings will advance the design of dynamic covalent and responsive biomaterials.