Total Chemical Synthesis of Lassomycin and Lassomycin-Amide

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

doi:10.1039/c6ob00631k

Total Chemical Synthesis of Lassomycin and Lassomycin-Amide

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

Authors

S. Lear

T. Munshi

A.S. Hudson

C. Hatton

J. Clardy

J.A. Mosely

T.J. Bull

C.S. Sit

Professor Steven Cobb s.l.cobb@durham.ac.uk
Professor

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 speculate that naturally occurring lassomycin may actually exhibit a standard lasso peptide threaded conformation rather than the previously reported unthreaded structure.

Citation

Lear, S., Munshi, T., Hudson, A., Hatton, C., Clardy, J., Mosely, J., …Cobb, S. (2016). Total Chemical Synthesis of Lassomycin and Lassomycin-Amide. Organic and Biomolecular Chemistry, 14(19), 4534-4541. https://doi.org/10.1039/c6ob00631k

Journal Article Type	Article
Acceptance Date	Apr 12, 2016
Online Publication Date	Apr 12, 2016
Publication Date	May 21, 2016
Deposit Date	Dec 4, 2015
Publicly Available Date	Apr 15, 2016
Journal	Organic and Biomolecular Chemistry
Print ISSN	1477-0520
Electronic ISSN	1477-0539
Publisher	Royal Society of Chemistry
Peer Reviewed	Peer Reviewed
Volume	14
Issue	19
Pages	4534-4541
DOI	https://doi.org/10.1039/c6ob00631k