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Aliphatic Ether Bond Formation Expands the Scope of Radical SAM Enzymes in Natural Product Biosynthesis.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2019 Jul 10; Vol. 141 (27), pp. 10610-10615. Date of Electronic Publication: 2019 Jun 27. - Publication Year :
- 2019
-
Abstract
- The biosynthetic pathways of microbial natural products provide a rich source of novel enzyme-catalyzed transformations. Using a new bioinformatic search strategy, we recently identified an abundance of gene clusters for ribosomally synthesized and post-translationally modified peptides (RiPPs) that contain at least one radical S -adenosylmethionine (RaS) metalloenzyme and are regulated by quorum sensing. In the present study, we characterize a RaS enzyme from one such RiPP gene cluster and find that it installs an aliphatic ether cross-link at an unactivated carbon center, linking the oxygen of a Thr side chain to the α-carbon of a Gln residue. This reaction marks the first ether cross-link installed by a RaS enzyme. Additionally, it leads to a new heterocyclization motif and underlines the utility of our bioinformatics approach in finding new families of RiPP modifications.
- Subjects :
- Amino Acid Sequence
Animals
Bacterial Proteins chemistry
Bacterial Proteins genetics
Biosynthetic Pathways
Computational Biology
Ethers metabolism
Peptides chemistry
Peptides genetics
Protein Processing, Post-Translational
Ribosomes genetics
Ribosomes metabolism
Streptococcal Infections microbiology
Streptococcal Infections veterinary
Streptococcus suis enzymology
Streptococcus suis genetics
Swine
Bacterial Proteins metabolism
Biological Products metabolism
Peptides metabolism
S-Adenosylmethionine metabolism
Streptococcus suis metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 141
- Issue :
- 27
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 31246011
- Full Text :
- https://doi.org/10.1021/jacs.9b05151