Total chemical synthesis of lassomycin and lassomycin-amide

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 activi...

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Published inOrganic & biomolecular chemistry Vol. 14; no. 19; pp. 4534 - 4541
Main Authors Lear, S., Munshi, T., Hudson, A. S., Hatton, C., Clardy, J., Mosely, J. A., Bull, T. J., Sit, C. S., Cobb, S. L.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Amide Synthases - chemistry
Amino Acid Sequence
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Organic
Molecular Conformation
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Physical Sciences
Protein Conformation
Science & Technology
PEPTIDES
PROTECTING GROUP
ACIDS
TUBERCULOSIS
BIOSYNTHESIS
ESTERS
CYCLIZATION
PROTEASE
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Summary: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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob00631k