Generating Selective Saccharide Binding Affinity of Phenyl Boronic Acids by using Single-Walled Carbon Nanotube Corona Phases

Bin Mu, Jiyoung Ahn, Thomas P. McNicholas, Michael S. Strano

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Saccharides recognition is challenging due to their low affinity for substrates, yet this recognition is critical for human immunity and glycobiology. Herein, we demonstrate that a polymer or surfactant corona phase surrounding a single-walled carbon nanotube can substantially modify the selectivity of pre-adsorbed phenylboronic acids (PBA) for mono-, di-, and poly-saccharides. A library of 17 PBAs including carboxy, nitro, and amino PBA with ortho-, meta-, or para- substitutions are used to generate 144 distinct corona phases. Six in particular demonstrate significantly increased selectivity to specific saccharides including ribose (0.42 mol per total mol), arabinose (0.36), and glucose (0.25), but unusually diminished binding to fructose (0.02). Recognition proceeds by saccharide adsorption into the corona, followed by PBA reaction in a consecutive second order reaction. The results extend to larger saccharides, such as glycosaminoglycans, suggesting promise for protein glycosylation.

Original languageEnglish (US)
Pages (from-to)4523-4528
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number12
DOIs
StatePublished - Mar 16 2015

Keywords

  • Cophmores
  • Molecular recognition
  • Nanotubes
  • Phenylboronic acid
  • Sensors

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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