Biosynthesis and Chemical Applications of Thioamides

Thioamidation as a posttranslational modification is exceptionally rare, with only a few reported natural products and exactly one known protein example (methyl-coenzyme M reductase from methane-metabolizing archaea). Recently, there has been significant progress in elucidating the biosynthesis and...

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Bibliographic Details
Published in:ACS chemical biology 2019-02, Vol.14 (2), p.142-163
Main Authors: Mahanta, Nilkamal, Szantai-Kis, D. Miklos, Petersson, E. James, Mitchell, Douglas A
Format: Article
Language:English
Subjects:
Biological Products - chemistry
Biological Products - pharmacology
Molecular Structure
Thioamides - chemistry
Thioamides - metabolism
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Summary:Thioamidation as a posttranslational modification is exceptionally rare, with only a few reported natural products and exactly one known protein example (methyl-coenzyme M reductase from methane-metabolizing archaea). Recently, there has been significant progress in elucidating the biosynthesis and function of several thioamide-containing natural compounds. Separate developments in the chemical installation of thioamides into peptides and proteins have enabled cell biology and biophysical studies to advance the current understanding of natural thioamides. This review highlights the various strategies used by Nature to install thioamides in peptidic scaffolds and the potential functions of this rare but important modification. We also discuss synthetic methods used for the site-selective incorporation of thioamides into polypeptides with a brief discussion of the physicochemical implications. This account will serve as a foundation for the further study of thioamides in natural products and their various applications.
ISSN:1554-8929
1554-8937
DOI:10.1021/acschembio.8b01022