Targeting bacteria via iminoboronate chemistry of amine-presenting lipids

Nature Communications
Anupam BandyopadhyayJianmin Gao

Abstract

Synthetic molecules that target specific lipids serve as powerful tools for understanding membrane biology and may also enable new applications in biotechnology and medicine. For example, selective recognition of bacterial lipids may give rise to novel antibiotics, as well as diagnostic methods for bacterial infection. Currently known lipid-binding molecules primarily rely on noncovalent interactions to achieve lipid selectivity. Here we show that targeted recognition of lipids can be realized by selectively modifying the lipid of interest via covalent bond formation. Specifically, we report an unnatural amino acid that preferentially labels amine-presenting lipids via iminoboronate formation under physiological conditions. By targeting phosphatidylethanolamine and lysylphosphatidylglycerol, the two lipids enriched on bacterial cell surfaces, the iminoboronate chemistry allows potent labelling of Gram-positive bacteria even in the presence of 10% serum, while bypassing mammalian cells and Gram-negative bacteria. The covalent strategy for lipid recognition should be extendable to other important membrane lipids.

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Citations

Feb 10, 2016·Journal of the American Chemical Society·Anupam Bandyopadhyay, Jianmin Gao
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Methods Mentioned

BETA
flow cytometry
fluorescence
genetic modification
NMR
Assay
dynamic light scattering

Software Mentioned

LAS
Fiji ImageJ
FlowJo

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