Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β-Peptide Bundle

Org Lett. 2015 Oct 2;17(19):4718-21. doi: 10.1021/acs.orglett.5b02187.

Abstract

The selective recruitment of oligosaccharides, or even simple sugars, in water solvent is an unsolved molecular recognition problem. Structure-guided, electrostatic redesign led to a significant increase in the affinity of a β-peptide "borono-bundle" for simple sugars in neutral aqueous solution. The affinity for fructose (663 M(-1)) in water should allow its recruitment to the bundle surface for selective catalysis, and future work will focus in this direction.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Carbohydrates / chemistry*
  • Fructose / chemistry
  • Glucose / chemistry
  • Molecular Structure
  • Oligosaccharides / chemistry
  • Peptides / chemistry*
  • Solvents
  • Sorbitol / chemistry
  • Static Electricity
  • Thermodynamics
  • Water / chemistry

Substances

  • Carbohydrates
  • Oligosaccharides
  • Peptides
  • Solvents
  • Water
  • Fructose
  • Sorbitol
  • Glucose