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Recombinant thiopeptides containing noncanonical amino acids.

ABSTRACT: Thiopeptides are a subclass of ribosomally synthesized and posttranslationally modified peptides (RiPPs) with complex molecular architectures and an array of biological activities, including potent antimicrobial activity. Here we report the generation of thiopeptides containing noncanonical amino acids (ncAAs) by introducing orthogonal amber suppressor aminoacyl-tRNA synthetase/tRNA pairs into a thiocillin producer strain of Bacillus cereus .We demonstrate that thiopeptide variants containing ncAAs with bioorthogonal chemical reactivity can be further postbiosynthetically modified with biophysical probes, including fluorophores and photo-cross-linkers. This work allows the site-specific incorporation of ncAAs into thiopeptides to increase their structural diversity and probe their biological activity; similar approaches can likely be applied to other classes of RiPPs.

SUBMITTER: Luo X 

PROVIDER: S-EPMC4822594 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Recombinant thiopeptides containing noncanonical amino acids.

Luo Xiaozhou X   Zambaldo Claudio C   Liu Tao T   Zhang Yuhan Y   Xuan Weimin W   Wang Chen C   Reed Sean A SA   Yang Peng-Yu PY   Wang Rongsheng E RE   Javahishvili Tsotne T   Schultz Peter G PG   Young Travis S TS  

Proceedings of the National Academy of Sciences of the United States of America 20160314 13

Thiopeptides are a subclass of ribosomally synthesized and posttranslationally modified peptides (RiPPs) with complex molecular architectures and an array of biological activities, including potent antimicrobial activity. Here we report the generation of thiopeptides containing noncanonical amino acids (ncAAs) by introducing orthogonal amber suppressor aminoacyl-tRNA synthetase/tRNA pairs into a thiocillin producer strain of Bacillus cereus .We demonstrate that thiopeptide variants containing nc  ...[more]

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