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

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

Author information

1
Department of Chemistry and ‡Department of Molecular, Cellular, and Developmental Biology, Yale University , New Haven, Connecticut 06520-8107, United States.

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.

PMID:
26376076
DOI:
10.1021/acs.orglett.5b02187
[Indexed for MEDLINE]

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