Total chemical synthesis of lassomycin and lassomycin-amide

S. Lear, T. Munshi, A. S. Hudson, C. Hatton, J. Clardy, J. A. Mosely, T. J. Bull, C. S. Sit, S. L. Cobb

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4534-4541
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number19
DOIs
Publication statusPublished - 12 Apr 2016

Bibliographical note

Funding 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.

Publisher Copyright:
© The Royal Society of Chemistry 2016.

Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.

Fingerprint Dive into the research topics of 'Total chemical synthesis of lassomycin and lassomycin-amide'. Together they form a unique fingerprint.

Cite this