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Issue 19, 2016
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Total chemical synthesis of lassomycin and lassomycin-amide

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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.

Graphical abstract: Total chemical synthesis of lassomycin and lassomycin-amide

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Publication details

The article was received on 23 Mar 2016, accepted on 12 Apr 2016 and first published on 12 Apr 2016


Article type: Paper
DOI: 10.1039/C6OB00631K
Org. Biomol. Chem., 2016,14, 4534-4541
  • Open access: Creative Commons BY license
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    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 and S. L. Cobb, Org. Biomol. Chem., 2016, 14, 4534
    DOI: 10.1039/C6OB00631K

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