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2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin
Radboud University Nijmegen, IMM Organic Chemistry, Heyendaalseweg 135, 6525 AJ, Nijmegen, the Netherlands
Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2300 RA, Leiden, the Netherlands
* Author to whom correspondence should be addressed.
Received: 18 December 2009; in revised form: 8 March 2010 / Accepted: 10 March 2010 / Published: 15 March 2010
(This article belongs to the Special Issue Antibiotics
Abstract: A small library of truncated neomycin-conjugates is prepared by consecutive removal of 2,6-diaminoglucose rings, oxidation-reductive amination of ribose, oxidation-conjugation of aminopyridine/aminoquinoline and finally dimerization. The dimeric conjugates were evaluated for antibacterial activity with a unique hemocyanin-based biosensor. Based on the outcome of these results, a second-generation set of monomeric conjugates was prepared and found to display significant antibacterial activity, in particular with respect to kanamycin-resistant E. coli.
Keywords: aminoglycosides; morpholine; aminopyridine; aminoquinoline; hemocyanin; biosensor; fluorescence
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MDPI and ACS Style
Aslam, M.W.; Tabares, L.C.; Andreoni, A.; Canters, G.W.; Rutjes, F.P.; Van Delft, F.L. 2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin. Pharmaceuticals 2010, 3, 679-701.
Aslam MW, Tabares LC, Andreoni A, Canters GW, Rutjes FP, Van Delft FL. 2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin. Pharmaceuticals. 2010; 3(3):679-701.
Aslam, M. Waqar; Tabares, Leandro C.; Andreoni, Alessio; Canters, Gerard W.; Rutjes, Floris P.J.T.; Van Delft, Floris L. 2010. "2-Deoxystreptamine Conjugates by Truncation–Derivatization of Neomycin." Pharmaceuticals 3, no. 3: 679-701.