With the proliferation of multi-drug resistant bacteria, the synthesis of novel antibiotics is of the utmost importance. As such, we propose to functionalize simplified analogues of common antibacterial agents—specifically certain well studied, but underexploited, aminoglycosides—to produce a library of new, potentially bactericidal molecules. Toward this end, we chemically modified the neamine-like substructure of the aminoglycosides butirosin B, neomycin, and paromomycin with azide and alkyne moieties, as depicted in Figure 1. In the future, via the high-yield azide-alkyne click reaction, each of these molecules will be 'clicked' with an array of alkyne- and azide-modified small molecules to produce a library of novel semi-synthetic aminoglycosides, as described in Figure 2. These semi-synthetic aminoglycosides will then be tested for antibacterial activity via antibiogram and, depending on the results obtained, further chemical modifications will be considered.

Synthesis of novel bactericidal aminoglycosides

249th National Meeting (2015)

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