Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide
Wolf F, Bauer JS, Bendel TM, Kulik A, Kalinowski J, Gross H, Kaysser L (2017)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56(23): 6665-6668.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Wolf, Felix;
Bauer, Judith S.;
Bendel, Theresa M.;
Kulik, Andreas;
Kalinowski, JörnUniBi;
Gross, Harald;
Kaysser, Leonard
Abstract / Bemerkung
Belactosins and cystargolides are natural product proteasome inhibitors from Actinobacteria. Both feature dipeptidic backbones and a unique beta-lactone building block. Herein, we present a detailed investigation of their biosynthesis. Identification and analysis of the corresponding gene clusters indicated that both compounds are assembled by rare single-enzyme amino acid ligases. Feeding experiments with isotope-labeled precursors and in vitro biochemistry showed that the formation of the beta-lactone warhead is unprecedented and reminiscent of leucine biosynthesis, and that it involves the action of isopropylmalate synthase homologues.
Stichworte
biosynthesis;
inhibitors;
lactones;
metabolism;
natural products
Erscheinungsjahr
2017
Zeitschriftentitel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Band
56
Ausgabe
23
Seite(n)
6665-6668
ISSN
1433-7851
eISSN
1521-3773
Page URI
https://pub.uni-bielefeld.de/record/2911994
Zitieren
Wolf F, Bauer JS, Bendel TM, et al. Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2017;56(23):6665-6668.
Wolf, F., Bauer, J. S., Bendel, T. M., Kulik, A., Kalinowski, J., Gross, H., & Kaysser, L. (2017). Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56(23), 6665-6668. doi:10.1002/anie.201612076
Wolf, Felix, Bauer, Judith S., Bendel, Theresa M., Kulik, Andreas, Kalinowski, Jörn, Gross, Harald, and Kaysser, Leonard. 2017. “Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56 (23): 6665-6668.
Wolf, F., Bauer, J. S., Bendel, T. M., Kulik, A., Kalinowski, J., Gross, H., and Kaysser, L. (2017). Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56, 6665-6668.
Wolf, F., et al., 2017. Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56(23), p 6665-6668.
F. Wolf, et al., “Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide”, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 56, 2017, pp. 6665-6668.
Wolf, F., Bauer, J.S., Bendel, T.M., Kulik, A., Kalinowski, J., Gross, H., Kaysser, L.: Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 56, 6665-6668 (2017).
Wolf, Felix, Bauer, Judith S., Bendel, Theresa M., Kulik, Andreas, Kalinowski, Jörn, Gross, Harald, and Kaysser, Leonard. “Biosynthesis of the beta-Lactone Proteasome Inhibitors Belactosin and Cystargolide”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.23 (2017): 6665-6668.
6 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Draft Genome Sequence of the Novonestmycin-Producing Strain Streptomyces sp. Z26, Isolated from Potato Rhizosphere in Morocco.
Buchmann A, Cano-Prieto C, Nafis A, Barakate M, Baz M, Hassani L, Ortlieb N, Niedermeyer THJ, Gross H., Microbiol Resour Announc 8(1), 2019
PMID: 30637404
Buchmann A, Cano-Prieto C, Nafis A, Barakate M, Baz M, Hassani L, Ortlieb N, Niedermeyer THJ, Gross H., Microbiol Resour Announc 8(1), 2019
PMID: 30637404
Biosynthesis and chemical diversity of β-lactone natural products.
Robinson SL, Christenson JK, Wackett LP., Nat Prod Rep 36(3), 2019
PMID: 30191940
Robinson SL, Christenson JK, Wackett LP., Nat Prod Rep 36(3), 2019
PMID: 30191940
The Tripod for Bacterial Natural Product Discovery: Genome Mining, Silent Pathway Induction, and Mass Spectrometry-Based Molecular Networking.
Trivella DBB, de Felicio R., mSystems 3(2), 2018
PMID: 29629418
Trivella DBB, de Felicio R., mSystems 3(2), 2018
PMID: 29629418
Characterization of the Actinonin Biosynthetic Gene Cluster.
Wolf F, Leipoldt F, Kulik A, Wibberg D, Kalinowski J, Kaysser L., Chembiochem (), 2018
PMID: 29600569
Wolf F, Leipoldt F, Kulik A, Wibberg D, Kalinowski J, Kaysser L., Chembiochem (), 2018
PMID: 29600569
Design, synthesis, and evaluation of cystargolide-based β-lactones as potent proteasome inhibitors.
Niroula D, Hallada LP, Le Chapelain C, Ganegamage SK, Dotson D, Rogelj S, Groll M, Tello-Aburto R., Eur J Med Chem 157(), 2018
PMID: 30165344
Niroula D, Hallada LP, Le Chapelain C, Ganegamage SK, Dotson D, Rogelj S, Groll M, Tello-Aburto R., Eur J Med Chem 157(), 2018
PMID: 30165344
Draft Genome Sequence of the Xanthocidin-Producing Strain Streptomyces sp. AcE210, Isolated from a Root Nodule of Alnus glutinosa (L.).
Ortlieb N, Keilhofer N, Schrey SD, Gross H, Niedermeyer THJ., Microbiol Resour Announc 7(14), 2018
PMID: 30533708
Ortlieb N, Keilhofer N, Schrey SD, Gross H, Niedermeyer THJ., Microbiol Resour Announc 7(14), 2018
PMID: 30533708
31 References
Daten bereitgestellt von Europe PubMed Central.
Proteolysis: from the lysosome to ubiquitin and the proteasome.
Ciechanover A., Nat. Rev. Mol. Cell Biol. 6(1), 2005
PMID: 15688069
Ciechanover A., Nat. Rev. Mol. Cell Biol. 6(1), 2005
PMID: 15688069
AUTHOR UNKNOWN, 0
Accumulation of p53 in a mutant cell line defective in the ubiquitin pathway.
Chowdary DR, Dermody JJ, Jha KK, Ozer HL., Mol. Cell. Biol. 14(3), 1994
PMID: 8114731
Chowdary DR, Dermody JJ, Jha KK, Ozer HL., Mol. Cell. Biol. 14(3), 1994
PMID: 8114731
Role of the ubiquitin-proteasome pathway in regulating abundance of the cyclin-dependent kinase inhibitor p27.
Pagano M, Tam SW, Theodoras AM, Beer-Romero P, Del Sal G, Chau V, Yew PR, Draetta GF, Rolfe M., Science 269(5224), 1995
PMID: 7624798
Pagano M, Tam SW, Theodoras AM, Beer-Romero P, Del Sal G, Chau V, Yew PR, Draetta GF, Rolfe M., Science 269(5224), 1995
PMID: 7624798
Inhibitors of the proteasome block the degradation of most cell proteins and the generation of peptides presented on MHC class I molecules.
Rock KL, Gramm C, Rothstein L, Clark K, Stein R, Dick L, Hwang D, Goldberg AL., Cell 78(5), 1994
PMID: 8087844
Rock KL, Gramm C, Rothstein L, Clark K, Stein R, Dick L, Hwang D, Goldberg AL., Cell 78(5), 1994
PMID: 8087844
AUTHOR UNKNOWN, 0
Epoxomicin and Eponemycin Biosynthesis Involves gem-Dimethylation and an Acyl-CoA Dehydrogenase-Like Enzyme.
Zettler J, Zubeil F, Kulik A, Grond S, Kaysser L., Chembiochem 17(9), 2016
PMID: 26789439
Zettler J, Zubeil F, Kulik A, Grond S, Kaysser L., Chembiochem 17(9), 2016
PMID: 26789439
Genetic basis for the biosynthesis of the pharmaceutically important class of epoxyketone proteasome inhibitors.
Schorn M, Zettler J, Noel JP, Dorrestein PC, Moore BS, Kaysser L., ACS Chem. Biol. 9(1), 2013
PMID: 24168704
Schorn M, Zettler J, Noel JP, Dorrestein PC, Moore BS, Kaysser L., ACS Chem. Biol. 9(1), 2013
PMID: 24168704
AUTHOR UNKNOWN, 0
Macyranones: Structure, Biosynthesis, and Binding Mode of an Unprecedented Epoxyketone that Targets the 20S Proteasome.
Keller L, Plaza A, Dubiella C, Groll M, Kaiser M, Muller R., J. Am. Chem. Soc. 137(25), 2015
PMID: 26050527
Keller L, Plaza A, Dubiella C, Groll M, Kaiser M, Muller R., J. Am. Chem. Soc. 137(25), 2015
PMID: 26050527
Multiplexed metagenome mining using short DNA sequence tags facilitates targeted discovery of epoxyketone proteasome inhibitors.
Owen JG, Charlop-Powers Z, Smith AG, Ternei MA, Calle PY, Reddy BV, Montiel D, Brady SF., Proc. Natl. Acad. Sci. U.S.A. 112(14), 2015
PMID: 25831524
Owen JG, Charlop-Powers Z, Smith AG, Ternei MA, Calle PY, Reddy BV, Montiel D, Brady SF., Proc. Natl. Acad. Sci. U.S.A. 112(14), 2015
PMID: 25831524
AUTHOR UNKNOWN, 0
Inhibitor-binding mode of homobelactosin C to proteasomes: new insights into class I MHC ligand generation.
Groll M, Larionov OV, Huber R, de Meijere A., Proc. Natl. Acad. Sci. U.S.A. 103(12), 2006
PMID: 16537370
Groll M, Larionov OV, Huber R, de Meijere A., Proc. Natl. Acad. Sci. U.S.A. 103(12), 2006
PMID: 16537370
Belactosin A, a novel antitumor antibiotic acting on cyclin/CDK mediated cell cycle regulation, produced by Streptomyces sp.
Asai A, Hasegawa A, Ochiai K, Yamashita Y, Mizukami T., J. Antibiot. 53(1), 2000
PMID: 10724015
Asai A, Hasegawa A, Ochiai K, Yamashita Y, Mizukami T., J. Antibiot. 53(1), 2000
PMID: 10724015
Cystargolides, 20S Proteasome Inhibitors Isolated from Kitasatospora cystarginea.
Gill KA, Berrue F, Arens JC, Carr G, Kerr RG., J. Nat. Prod. 78(4), 2015
PMID: 25769015
Gill KA, Berrue F, Arens JC, Carr G, Kerr RG., J. Nat. Prod. 78(4), 2015
PMID: 25769015
Biosynthesis of the salinosporamide A polyketide synthase substrate chloroethylmalonyl-coenzyme A from S-adenosyl-L-methionine.
Eustaquio AS, McGlinchey RP, Liu Y, Hazzard C, Beer LL, Florova G, Alhamadsheh MM, Lechner A, Kale AJ, Kobayashi Y, Reynolds KA, Moore BS., Proc. Natl. Acad. Sci. U.S.A. 106(30), 2009
PMID: 19590008
Eustaquio AS, McGlinchey RP, Liu Y, Hazzard C, Beer LL, Florova G, Alhamadsheh MM, Lechner A, Kale AJ, Kobayashi Y, Reynolds KA, Moore BS., Proc. Natl. Acad. Sci. U.S.A. 106(30), 2009
PMID: 19590008
Mining the cinnabaramide biosynthetic pathway to generate novel proteasome inhibitors.
Rachid S, Huo L, Herrmann J, Stadler M, Kopcke B, Bitzer J, Muller R., Chembiochem 12(6), 2011
PMID: 21387511
Rachid S, Huo L, Herrmann J, Stadler M, Kopcke B, Bitzer J, Muller R., Chembiochem 12(6), 2011
PMID: 21387511
Biosynthesis of ebelactone A: isotopic tracer, advanced precursor and genetic studies reveal a thioesterase-independent cyclization to give a polyketide β-lactone.
Wyatt MA, Ahilan Y, Argyropoulos P, Boddy CN, Magarvey NA, Harrison PH., J. Antibiot. 66(7), 2013
PMID: 23801186
Wyatt MA, Ahilan Y, Argyropoulos P, Boddy CN, Magarvey NA, Harrison PH., J. Antibiot. 66(7), 2013
PMID: 23801186
Operon for biosynthesis of lipstatin, the Beta-lactone inhibitor of human pancreatic lipase.
Bai T, Zhang D, Lin S, Long Q, Wang Y, Ou H, Kang Q, Deng Z, Liu W, Tao M., Appl. Environ. Microbiol. 80(24), 2014
PMID: 25239907
Bai T, Zhang D, Lin S, Long Q, Wang Y, Ou H, Kang Q, Deng Z, Liu W, Tao M., Appl. Environ. Microbiol. 80(24), 2014
PMID: 25239907
antiSMASH 2.0--a versatile platform for genome mining of secondary metabolite producers.
Blin K, Medema MH, Kazempour D, Fischbach MA, Breitling R, Takano E, Weber T., Nucleic Acids Res. 41(Web Server issue), 2013
PMID: 23737449
Blin K, Medema MH, Kazempour D, Fischbach MA, Breitling R, Takano E, Weber T., Nucleic Acids Res. 41(Web Server issue), 2013
PMID: 23737449
PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin.
Gust B, Challis GL, Fowler K, Kieser T, Chater KF., Proc. Natl. Acad. Sci. U.S.A. 100(4), 2003
PMID: 12563033
Gust B, Challis GL, Fowler K, Kieser T, Chater KF., Proc. Natl. Acad. Sci. U.S.A. 100(4), 2003
PMID: 12563033
Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891.
Steffensky M, Li SM, Heide L., J. Biol. Chem. 275(28), 2000
PMID: 10801869
Steffensky M, Li SM, Heide L., J. Biol. Chem. 275(28), 2000
PMID: 10801869
Kinetic and chemical mechanism of alpha-isopropylmalate synthase from Mycobacterium tuberculosis.
de Carvalho LP, Blanchard JS., Biochemistry 45(29), 2006
PMID: 16846242
de Carvalho LP, Blanchard JS., Biochemistry 45(29), 2006
PMID: 16846242
MAM3 catalyzes the formation of all aliphatic glucosinolate chain lengths in Arabidopsis.
Textor S, de Kraker JW, Hause B, Gershenzon J, Tokuhisa JG., Plant Physiol. 144(1), 2007
PMID: 17369439
Textor S, de Kraker JW, Hause B, Gershenzon J, Tokuhisa JG., Plant Physiol. 144(1), 2007
PMID: 17369439
An ATP-independent strategy for amide bond formation in antibiotic biosynthesis.
Funabashi M, Yang Z, Nonaka K, Hosobuchi M, Fujita Y, Shibata T, Chi X, Van Lanen SG., Nat. Chem. Biol. 6(8), 2010
PMID: 20562876
Funabashi M, Yang Z, Nonaka K, Hosobuchi M, Fujita Y, Shibata T, Chi X, Van Lanen SG., Nat. Chem. Biol. 6(8), 2010
PMID: 20562876
The ATP-grasp enzymes.
Fawaz MV, Topper ME, Firestine SM., Bioorg. Chem. 39(5-6), 2011
PMID: 21920581
Fawaz MV, Topper ME, Firestine SM., Bioorg. Chem. 39(5-6), 2011
PMID: 21920581
Dapdiamides, tripeptide antibiotics formed by unconventional amide ligases.
Dawlaty J, Zhang X, Fischbach MA, Clardy J., J. Nat. Prod. 73(3), 2010
PMID: 20041689
Dawlaty J, Zhang X, Fischbach MA, Clardy J., J. Nat. Prod. 73(3), 2010
PMID: 20041689
AUTHOR UNKNOWN, 0
Identification and analysis of the resorcinomycin biosynthetic gene cluster.
Ooya K, Ogasawara Y, Noike M, Dairi T., Biosci. Biotechnol. Biochem. 79(11), 2015
PMID: 26034896
Ooya K, Ogasawara Y, Noike M, Dairi T., Biosci. Biotechnol. Biochem. 79(11), 2015
PMID: 26034896
A peptide ligase and the ribosome cooperate to synthesize the peptide pheganomycin.
Noike M, Matsui T, Ooya K, Sasaki I, Ohtaki S, Hamano Y, Maruyama C, Ishikawa J, Satoh Y, Ito H, Morita H, Dairi T., Nat. Chem. Biol. 11(1), 2014
PMID: 25402768
Noike M, Matsui T, Ooya K, Sasaki I, Ohtaki S, Hamano Y, Maruyama C, Ishikawa J, Satoh Y, Ito H, Morita H, Dairi T., Nat. Chem. Biol. 11(1), 2014
PMID: 25402768
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 28452105
PubMed | Europe PMC
Suchen in
Google Scholar