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

Org Lett

Department of Chemistry and ‡Department of Molecular, Cellular, and Developmental Biology, Yale University, New Haven, Connecticut 06520-8107, United States.

Published: October 2015

AI Article Synopsis

  • The recruitment of oligosaccharides and simple sugars in water is currently an unsolved issue in molecular recognition.
  • Structure-guided redesign of a β-peptide "borono-bundle" improved its ability to attract simple sugars in neutral water.
  • Its strong affinity for fructose (663 M(-1)) suggests potential for selective catalysis, with upcoming research aimed at exploring this application.

Article 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.

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Source
http://dx.doi.org/10.1021/acs.orglett.5b02187DOI Listing

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