Disaccharide mimetics of the aminoglycoside antibiotic neamine

Chembiochem : a European Journal of Chemical Biology
Andre VenotGeert-Jan Boons

Abstract

A highly convergent approach has been employed for the facile synthesis of a library of 24 disaccharides that are alpha(1-3), beta(1-3), alpha(1-4), or beta(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 (Kd) 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.

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Citations

Nov 13, 2009·Journal of the American Chemical Society·Sailaja ArungundramGeert-Jan Boons
Jan 9, 2013·Organic Letters·Chengli ZongGeert-Jan Boons
Mar 25, 2006·Organic & Biomolecular Chemistry·Yu RaoGeert-Jan Boons
Dec 12, 2012·The Journal of Organic Chemistry·Wenxuan ZhangZhongjun Li
Jun 19, 2013·The Journal of Organic Chemistry·Ernest G NolenKristopher V Waynant
Dec 24, 2010·Bioorganic & Medicinal Chemistry·Ri-Bai YanXin-Shan Ye
Feb 5, 2011·Biochimica Et Biophysica Acta·Myriam OuberaiMarie-Paule Mingeot-Leclercq
Feb 20, 2014·Organic & Biomolecular Chemistry·Omkar P DhamaleGeert-Jan Boons
Nov 14, 2018·Chembiochem : a European Journal of Chemical Biology·Yen-Chu LuKwok-Kong Tony Mong
Aug 8, 2006·Medicinal Research Reviews·Jian ZhouXin-Shan Ye
Mar 10, 2005·Chemical Reviews·Guuske F BusscherFloris L van Delft
Mar 26, 2008·Chemical Reviews·Jason R Thomas, Paul J Hergenrother

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