Herein we report a practical synthetic route to the lasso peptide lassomycin (1) and C-terminal variant lassomycin-amide (2). The biological evaluation of peptides 1 and 2 against Mycobacterium tuberculosis revealed that neither had any activity against this bacterium. This lack of biological activity has led us to propose that naturally occurring lassomycin may actually exhibit a standard lasso peptide threaded conformation rather than the previously reported unthreaded structure.
Bibliographical noteFunding Information:
We gratefully acknowledge financial support from the EPSRC (Durham University EPSRC DTG, SL). CSS was funded by an Alberta Innovates Health Solutions Fellowship and a Banting Postdoctoral Fellowship. In addition, we thank Dr Juan A. Aguilar Malavia (Durham University) for the collection and processing of 2D NMR data.
© The Royal Society of Chemistry 2016.
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