Posttranslational chemical installation of azoles into translated peptides

Azoles are five-membered heterocycles often found in the backbones of peptidic natural products and synthetic peptidomimetics. Here, we report a method of ribosomal synthesis of azole-containing peptides involving specific ribosomal incorporation of a bromovinylglycine derivative into the nascent pe...

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Bibliographic Details
Published in:Nature communications 2021-01, Vol.12 (1), p.696-696, Article 696
Main Authors: Tsutsumi, Haruka, Kuroda, Tomohiro, Kimura, Hiroyuki, Goto, Yuki, Suga, Hiroaki
Format: Article
Language:English
Subjects:
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Aqueous solutions
Azoles
Azoles - chemistry
Azoles - metabolism
Biomimetics - methods
Chains
Chemical modification
Conversion
Drug Design
Heterocyclic compounds
Humanities and Social Sciences
In vitro methods and tests
Isomerization
mRNA
multidisciplinary
Natural products
Oxazole
Peptide Biosynthesis
Peptides
Peptides - chemistry
Peptides - metabolism
Peptidomimetics
Peptidomimetics - chemistry
Peptidomimetics - metabolism
Protein Processing, Post-Translational
Science
Science (multidisciplinary)
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Summary:Azoles are five-membered heterocycles often found in the backbones of peptidic natural products and synthetic peptidomimetics. Here, we report a method of ribosomal synthesis of azole-containing peptides involving specific ribosomal incorporation of a bromovinylglycine derivative into the nascent peptide chain and its chemoselective conversion to a unique azole structure. The chemoselective conversion was achieved by posttranslational dehydrobromination of the bromovinyl group and isomerization in aqueous media under fairly mild conditions. This method enables us to install exotic azole groups, oxazole and thiazole, at designated positions in the peptide chain with both linear and macrocyclic scaffolds and thereby expand the repertoire of building blocks in the mRNA-templated synthesis of designer peptides. Azoles are five-membered heterocycles found in peptidic natural products and synthetic peptiodomimetics. Here the authors demonstrate a posttranslational chemical modification method for in vitro ribosomal synthesis of peptides with exotic azole groups at specific positions.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-021-20992-0