Flexizyme-Enabled Benchtop Biosynthesis of Thiopeptides.


Journal

Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056

Informations de publication

Date de publication:
16 01 2019
Historique:
pubmed: 3 1 2019
medline: 4 6 2020
entrez: 3 1 2019
Statut: ppublish

Résumé

Thiopeptides are natural antibiotics that are fashioned from short peptides by multiple layers of post-translational modification. Their biosynthesis, in particular the pyridine synthases that form the macrocyclic antibiotic core, has attracted intensive research but is complicated by the challenges of reconstituting multiple-pathway enzymes. By combining select RiPP enzymes with cell free expression and flexizyme-based codon reprogramming, we have developed a benchtop biosynthesis of thiopeptide scaffolds. This strategy side-steps several challenges related to the investigation of thiopeptide enzymes and allows access to analytical quantities of new thiopeptide analogs. We further demonstrate that this strategy can be used to validate the activity of new pyridine synthases without the need to reconstitute the cognate prior pathway enzymes.

Identifiants

pubmed: 30602112
doi: 10.1021/jacs.8b11521
pmc: PMC6642631
mid: NIHMS1040879
doi:

Substances chimiques

Anti-Bacterial Agents 0
Aptamers, Nucleotide 0
Peptides, Cyclic 0
RNA, Catalytic 0
Thiazoles 0

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

758-762

Subventions

Organisme : NIGMS NIH HHS
ID : R35 GM125005
Pays : United States

Références

Org Lett. 2000 Nov 16;2(23):3603-6
pubmed: 11073655
J Am Chem Soc. 2006 Jun 7;128(22):7150-1
pubmed: 16734454
Mol Cell. 2008 Apr 11;30(1):26-38
pubmed: 18406324
Nat Chem Biol. 2010 Jan;6(1):9-18
pubmed: 20016494
J Am Chem Soc. 2010 Jun 2;132(21):7519-27
pubmed: 20455532
Nucleic Acids Res. 2010 Jul;38(13):e141
pubmed: 20457746
Nat Protoc. 2011 Jun;6(6):779-90
pubmed: 21637198
ACS Chem Biol. 2012 Mar 16;7(3):429-42
pubmed: 22206579
Nucleic Acids Res. 2012 Sep;40(16):7932-45
pubmed: 22723376
Nat Prod Rep. 2013 Jan;30(1):108-60
pubmed: 23165928
Nat Prod Rep. 2013 Feb;30(2):218-26
pubmed: 23250571
Chem Biol. 2012 Dec 21;19(12):1600-10
pubmed: 23261603
ACS Synth Biol. 2013 Jul 19;2(7):397-404
pubmed: 23654279
ACS Synth Biol. 2015 Feb 20;4(2):167-76
pubmed: 24625112
Chem Biol. 2014 May 22;21(5):679-88
pubmed: 24768308
Chem Biol. 2014 Jun 19;21(6):766-74
pubmed: 24856821
Angew Chem Int Ed Engl. 2014 Jun 23;53(26):6602-16
pubmed: 24861213
ACS Chem Biol. 2015 Apr 17;10(4):998-1009
pubmed: 25572285
J Am Chem Soc. 2015 Mar 18;137(10):3494-7
pubmed: 25742119
Nat Chem Biol. 2015 Aug;11(8):558-563
pubmed: 26098679
Chem Biol. 2015 Jul 23;22(7):907-16
pubmed: 26165156
J Am Chem Soc. 2015 Dec 30;137(51):16012-5
pubmed: 26675417
Nat Chem. 2016 Apr;8(4):317-25
pubmed: 27001726
J Am Chem Soc. 2016 Oct 19;138(41):13461-13464
pubmed: 27575591
J Am Chem Soc. 2016 Dec 7;138(48):15511-15514
pubmed: 27700071
Proc Natl Acad Sci U S A. 2016 Nov 1;113(44):12450-12455
pubmed: 27791142
Nat Commun. 2017 Feb 06;8:14207
pubmed: 28165449
J Am Chem Soc. 2017 Feb 22;139(7):2541-2544
pubmed: 28170244
Curr Opin Biotechnol. 2017 Dec;48:210-219
pubmed: 28672170
ACS Cent Sci. 2017 Jun 28;3(6):629-638
pubmed: 28691075
Proc Natl Acad Sci U S A. 2017 Dec 5;114(49):12928-12933
pubmed: 29158402
Curr Opin Microbiol. 2018 Oct;45:61-69
pubmed: 29533845
Curr Opin Chem Biol. 2018 Oct;46:82-90
pubmed: 29957445
J Am Chem Soc. 2018 Aug 1;140(30):9494-9501
pubmed: 29983054

Auteurs

Steven R Fleming (SR)

Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599 , United States.

Tessa E Bartges (TE)

Department of Chemistry , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599 , United States.

Alexander A Vinogradov (AA)

Department of Chemistry, Graduate School of Science , The University of Tokyo , Bunkyo-ku , Tokyo 113-0033 , Japan.
JST , PRESTO , 7-3-1 Hongo , Bunkyo-ku , Tokyo 113-0033 , Japan.

Christine L Kirkpatrick (CL)

Department of Chemistry , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599 , United States.

Yuki Goto (Y)

Department of Chemistry, Graduate School of Science , The University of Tokyo , Bunkyo-ku , Tokyo 113-0033 , Japan.
JST , PRESTO , 7-3-1 Hongo , Bunkyo-ku , Tokyo 113-0033 , Japan.

Hiroaki Suga (H)

Department of Chemistry, Graduate School of Science , The University of Tokyo , Bunkyo-ku , Tokyo 113-0033 , Japan.
JST , CREST , 7-3-1 Hongo , Bunkyo-ku , Tokyo 113-0033 , Japan.

Leslie M Hicks (LM)

Department of Chemistry , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599 , United States.

Albert A Bowers (AA)

Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599 , United States.

Articles similaires

Vancomycin-associated DRESS demonstrates delay in AST abnormalities.

Ahmed Hussein, Kateri L Schoettinger, Jourdan Hydol-Smith et al.
1.00
Humans Drug Hypersensitivity Syndrome Vancomycin Female Male
Humans Arthroplasty, Replacement, Elbow Prosthesis-Related Infections Debridement Anti-Bacterial Agents
Animals Hemiptera Insect Proteins Phylogeny Insecticides
Vancomycin Polyesters Anti-Bacterial Agents Models, Theoretical Drug Liberation

Classifications MeSH