Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions

Weiz AR, Ishida K, Quitterer F, Meyer S, Kehr J-C, Müller K, Groll M, Hertweck C, Dittmann E (2014)
Angewandte Chemie International Edition 53(14): 3735-3738.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Weiz, Annika R.; Ishida, Keishi; Quitterer, Felix; Meyer, Sabine; Kehr, Jan-Christoph; Müller, KristianUniBi ; Groll, Michael; Hertweck, Christian; Dittmann, Elke
Einrichtung
Technische Fakultät > AG Zelluläre und molekulare Biotechnologie
Abstract / Bemerkung
Understanding and controlling proteolysis is an important goal in therapeutic chemistry. Among the natural products specifically inhibiting proteases microviridins are particularly noteworthy. Microviridins are ribosomally produced and posttranslationally modified peptides that are processed into a unique, cagelike architecture. Here, we report a combined rational and random mutagenesis approach that provides fundamental insights into selectivity-conferring moieties of microviridins. The potent variant microviridin J was co-crystallized with trypsin, and for the first time the three-dimensional structure of microviridins was determined and the mode of inhibition revealed.
Stichworte
peptide engineering; cyanobacteria; RiPPs; structure elucidation; protease inhibitors
Erscheinungsjahr
2014
Zeitschriftentitel
Angewandte Chemie International Edition
Band
53
Ausgabe
14
Seite(n)
3735-3738
ISSN
1433-7851
Page URI
https://pub.uni-bielefeld.de/record/2684340

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Weiz AR, Ishida K, Quitterer F, et al. Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions. Angewandte Chemie International Edition. 2014;53(14):3735-3738.
Weiz, A. R., Ishida, K., Quitterer, F., Meyer, S., Kehr, J. - C., Müller, K., Groll, M., et al. (2014). Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions. Angewandte Chemie International Edition, 53(14), 3735-3738. doi:10.1002/anie.201309721
Weiz, Annika R., Ishida, Keishi, Quitterer, Felix, Meyer, Sabine, Kehr, Jan-Christoph, Müller, Kristian, Groll, Michael, Hertweck, Christian, and Dittmann, Elke. 2014. “Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions”. Angewandte Chemie International Edition 53 (14): 3735-3738.
Weiz, A. R., Ishida, K., Quitterer, F., Meyer, S., Kehr, J. - C., Müller, K., Groll, M., Hertweck, C., and Dittmann, E. (2014). Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions. Angewandte Chemie International Edition 53, 3735-3738.
Weiz, A.R., et al., 2014. Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions. Angewandte Chemie International Edition, 53(14), p 3735-3738.
A.R. Weiz, et al., “Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions”, Angewandte Chemie International Edition, vol. 53, 2014, pp. 3735-3738.
Weiz, A.R., Ishida, K., Quitterer, F., Meyer, S., Kehr, J.-C., Müller, K., Groll, M., Hertweck, C., Dittmann, E.: Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions. Angewandte Chemie International Edition. 53, 3735-3738 (2014).
Weiz, Annika R., Ishida, Keishi, Quitterer, Felix, Meyer, Sabine, Kehr, Jan-Christoph, Müller, Kristian, Groll, Michael, Hertweck, Christian, and Dittmann, Elke. “Harnessing the Evolvability of Tricyclic Microviridins To Dissect Protease-Inhibitor Interactions”. Angewandte Chemie International Edition 53.14 (2014): 3735-3738.

5 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

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PMID: 29725007
Exploration of the Biosynthetic Potential of the Populus Microbiome.
Blair PM, Land ML, Piatek MJ, Jacobson DA, Lu TS, Doktycz MJ, Pelletier DA., mSystems 3(5), 2018
PMID: 30320216
A Self-Sacrificing N-Methyltransferase Is the Precursor of the Fungal Natural Product Omphalotin.
Ramm S, Krawczyk B, Mühlenweg A, Poch A, Mösker E, Süssmuth RD., Angew Chem Int Ed Engl 56(33), 2017
PMID: 28715095
Leader Peptide-Free In Vitro Reconstitution of Microviridin Biosynthesis Enables Design of Synthetic Protease-Targeted Libraries.
Reyna-González E, Schmid B, Petras D, Süssmuth RD, Dittmann E., Angew Chem Int Ed Engl 55(32), 2016
PMID: 27336908
Natural Product Biosynthetic Diversity and Comparative Genomics of the Cyanobacteria.
Dittmann E, Gugger M, Sivonen K, Fewer DP., Trends Microbiol 23(10), 2015
PMID: 26433696

23 References

Daten bereitgestellt von Europe PubMed Central.

Targeting proteases: successes, failures and future prospects.
Turk B., Nat Rev Drug Discov 5(9), 2006
PMID: 16955069
Cyanobacterial peptides - nature's own combinatorial biosynthesis.
Welker M, von Dohren H., FEMS Microbiol. Rev. 30(4), 2006
PMID: 16774586

Ishitsuka, J. Am. Chem. Soc. 112(), 1990
Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature.
Arnison PG, Bibb MJ, Bierbaum G, Bowers AA, Bugni TS, Bulaj G, Camarero JA, Campopiano DJ, Challis GL, Clardy J, Cotter PD, Craik DJ, Dawson M, Dittmann E, Donadio S, Dorrestein PC, Entian KD, Fischbach MA, Garavelli JS, Goransson U, Gruber CW, Haft DH, Hemscheidt TK, Hertweck C, Hill C, Horswill AR, Jaspars M, Kelly WL, Klinman JP, Kuipers OP, Link AJ, Liu W, Marahiel MA, Mitchell DA, Moll GN, Moore BS, Muller R, Nair SK, Nes IF, Norris GE, Olivera BM, Onaka H, Patchett ML, Piel J, Reaney MJ, Rebuffat S, Ross RP, Sahl HG, Schmidt EW, Selsted ME, Severinov K, Shen B, Sivonen K, Smith L, Stein T, Sussmuth RD, Tagg JR, Tang GL, Truman AW, Vederas JC, Walsh CT, Walton JD, Wenzel SC, Willey JM, van der Donk WA., Nat Prod Rep 30(1), 2013
PMID: 23165928

AUTHOR UNKNOWN, 0
Post-translational modification in microviridin biosynthesis.
Philmus B, Christiansen G, Yoshida WY, Hemscheidt TK., Chembiochem 9(18), 2008
PMID: 19035375

Ziemert, Angew. Chem. 120(), 2008
Ribosomal synthesis of tricyclic depsipeptides in bloom-forming cyanobacteria.
Ziemert N, Ishida K, Liaimer A, Hertweck C, Dittmann E., Angew. Chem. Int. Ed. Engl. 47(40), 2008
PMID: 18683268
Substrate specificity and scope of MvdD, a GRASP-like ligase from the microviridin biosynthetic gene cluster.
Philmus B, Guerrette JP, Hemscheidt TK., ACS Chem. Biol. 4(6), 2009
PMID: 19445532
Leader peptide and a membrane protein scaffold guide the biosynthesis of the tricyclic peptide microviridin.
Weiz AR, Ishida K, Makower K, Ziemert N, Hertweck C, Dittmann E., Chem. Biol. 18(11), 2011
PMID: 22118675

AUTHOR UNKNOWN, 0

Murakami, Phytochemistry 45(), 1997

Okino, Tetrahedron 51(), 1995
Cyanobacterial protease inhibitor microviridin J causes a lethal molting disruption in Daphnia pulicaria.
Rohrlack T, Christoffersen K, Kaebernick M, Neilan BA., Appl. Environ. Microbiol. 70(8), 2004
PMID: 15294849

Shin, Tetrahedron 52(), 1996
Exploiting the natural diversity of microviridin gene clusters for discovery of novel tricyclic depsipeptides.
Ziemert N, Ishida K, Weiz A, Hertweck C, Dittmann E., Appl. Environ. Microbiol. 76(11), 2010
PMID: 20363789
Atomic structure of the trypsin-A90720A complex: a unified approach to structure and function.
Lee AY, Smitka TA, Bonjouklian R, Clardy J., Chem. Biol. 1(2), 1994
PMID: 9383379

AUTHOR UNKNOWN, 0
Cyanopeptolins, new depsipeptides from the cyanobacterium Microcystis sp. PCC 7806.
Martin C, Oberer L, Ino T, Konig WA, Busch M, Weckesser J., J. Antibiot. 46(10), 1993
PMID: 8244882
Binding structure of elastase inhibitor scyptolin A.
Matern U, Schleberger C, Jelakovic S, Weckesser J, Schulz GE., Chem. Biol. 10(10), 2003
PMID: 14583266
Potent elastase inhibitors from cyanobacteria: structural basis and mechanisms mediating cytoprotective and anti-inflammatory effects in bronchial epithelial cells.
Salvador LA, Taori K, Biggs JS, Jakoncic J, Ostrov DA, Paul VJ, Luesch H., J. Med. Chem. 56(3), 2013
PMID: 23350733
Comparison of cyanopeptolin genes in Planktothrix, Microcystis, and Anabaena strains: evidence for independent evolution within each genus.
Rounge TB, Rohrlack T, Tooming-Klunderud A, Kristensen T, Jakobsen KS., Appl. Environ. Microbiol. 73(22), 2007
PMID: 17921284
Discovery, biosynthesis, and engineering of lantipeptides.
Knerr PJ, van der Donk WA., Annu. Rev. Biochem. 81(), 2012
PMID: 22404629
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