Disaccharide mimetics of the aminoglycoside antibiotic neamine

Andre Venot; Eric E. Swayze; Richard H. Griffey; Geert Jan Boons

doi:10.1002/cbic.200400105

Disaccharide mimetics of the aminoglycoside antibiotic neamine

Andre Venot, Eric E. Swayze, Richard H. Griffey, Geert Jan Boons^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

A highly convergent approach has been employed for the facile synthesis of a library of 24 disaccharides that are α(1-3), β(1-3), α(1-4), or β(1-4) linked and contain 2-4 amino groups. Fourier-transformation ion cyclotron resonance mass spectrometry (FT-ICR MS) has been used to determine dissociation constant (K_d) values for the binding of the disaccharides to a prototypical fragment of 16S ribosomal RNA. Several derivatives bound with affinities similar to that of neamine. Structure-activity relationships have revealed the substitution pattern that is important for high-affinity binding. The compounds described here are unique lead compounds for the design of novel aminoglycoside antibiotics.

Original language	English
Pages (from-to)	1228-1236
Number of pages	9
Journal	ChemBioChem
Volume	5
Issue number	9
DOIs	https://doi.org/10.1002/cbic.200400105
Publication status	Published - 6 Sept 2004
Externally published	Yes

Keywords

Aminoglycosides
Antibiotics
Glycosylations
RNA
Substituent effects

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10.1002/cbic.200400105

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Disaccharide mimetics of the aminoglycoside antibiotic neamine

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Keywords

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