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

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

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. Th...

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Veröffentlicht in:Organic letters 2015-10, Vol.17 (19), p.4718-4721
Hauptverfasser: Melicher, Michael S, Walker, Allison S, Shen, John, Miller, Scott J, Schepartz, Alanna
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates - chemistry
Fructose - chemistry
Glucose - chemistry
Molecular Structure
Oligosaccharides - chemistry
Peptides - chemistry
Solvents
Sorbitol - chemistry
Static Electricity
Thermodynamics
Water - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02187