Journal
JOURNAL OF NATURAL PRODUCTS
Volume 76, Issue 9, Pages 1627-1636Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np4003096
Keywords
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Funding
- NIH [R37 AI52218]
- National Center for Advancing Translational Sciences [UL1TR000117]
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A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2'-amino-alpha-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.
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