Function of the loading module in CorI and of the O-methyltransferase CorH in vinyl carbamate biosynthesis of the antibiotic corallopyronin A

Antimicrobial Agents and Chemotherapy

Volumn 58, Issue 2, 2014, Pages 950-956

  Schäberle, Till F ^a   Mohseni, Mahsa Mir ^a   Lohr, Friederike ^a   Schmitz, Alexander ^a   König, Gabriele M ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; BICARBONATE; CARBAMIC ACID; CARBAMIC ACID VINYL ESTER; CARBONIC ACID; CORALLOPYRONIN A; CORH ENZYME; CORI ENZYME; METHYLTRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; DRUG STRUCTURE; ESCHERICHIA COLI; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION;

AMINO ACID MOTIFS; ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; CARBONIC ACID; DNA-DIRECTED RNA POLYMERASES; ESCHERICHIA COLI; ESTERS; GENE EXPRESSION; LACTONES; METHYLATION; METHYLTRANSFERASES; MOLECULAR SEQUENCE DATA; MYXOCOCCALES; RECOMBINANT PROTEINS; URETHANE;

EID: 84893461441     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01894-13     Document Type: Article

References (25)

1. Irschik H, Jansen R, Höfle G, Gerth K, Reichenbach H. 1985. The corallopyronins, new inhibitors of bacterial RNA synthesis from myxobacteria. J. Antibiot. 38:145-152. http://dx.doi.org/10.7164/antibiotics.38.145.
2. Erol O, Schäberle TF, Schmitz A, Rachid S, Gurgui C, El Omari M, Lohr F, Kehraus S, Piel J, Müller R, König GM. 2010. Biosynthesis of the myxobacterial antibiotic corallopyronin A. Chembiochem 11:1253-1265. http://dx.doi.org/10.1002/cbic.201000085.
3. Mukhopadhyay J, Das K, Ismail S, Koppstein D, Jang M, Hudson B, Sarafianos S, Tuske S, Patel J, Jansen R, Irschik H, Arnold E, Ebright RH. 2008. The RNA polymerase "switch region" is a target for inhibitors. Cell 135:295-307. http://dx.doi.org/10.1016/j.cell.2008.09.033.
4. Belogurov GA, Vassylyeva MN, Sevostyanova A, Appleman JR, Xiang AX, Lira R, Webber SE, Klyuyev S, Nudler E, Artsimovitch I, Vassylyev DG. 2009. Transcription inactivation through local refolding of the RNA polymerase structure. Nature 457:332-335. http://dx.doi.org/10.1038/nature07510.
5. Schiefer A, Schmitz A, Schäberle TF, Specht S, Lämmer C, Johnston KL, Vassylyev DG, König GM, Hoerauf A, Pfarr K. 2012. Corallopyronin A specifically targets and depletes essential obligate Wolbachia endobacteria from filarial nematodes in vivo. J. Infect. Dis. 206:249-257. http://dx.doi.org/10.1093/infdis/jis341.
6. Hoerauf A, Nissen-Pähle K, Schmetz C, Henkle-Dührsen K, Blaxter ML, Büttner DW, Gallin MY, Al-Qaoud KM, Lucius R, Fleischer B. 1999. Tetracycline therapy targets intracellular bacteria in the filarial nematode Litomosoides sigmodontis and results in filarial infertility. J. Clin. Invest. 103:11-18. http://dx.doi.org/10.1172/JCI4768.
7. Bockarie MJ, Taylor MJ, Gyapong JO. 2009. Current practices in the management of lymphatic filariasis. Expert Rev. Anti Infect. Ther. 7:595-605. http://dx.doi.org/10.1586/eri.09.36.
8. Campbell EA, Korzheva N, Mustaev A, Murakami K, Nair S, Goldfarb A, Darst SA. 2001. Structural mechanism for rifampicin inhibition of bacterial RNA polymerase. Cell 104:901-912. http://dx.doi.org/10.1016/S0092-8674(01)00286-0.
9. Hertweck C. 2009. The biosynthetic logic of polyketide diversity. Angew. Chem. Int. Ed. Engl. 48:4688-4716. http://dx.doi.org/10.1002/anie.200806121.
10. Piel J. 2010. Biosynthesis of polyketides by trans-AT polyketide synthases. Nat. Prod. Rep. 27:996-1047. http://dx.doi.org/10.1039/b816430b.
11. Schäberle TF, Siba C, Höver T, König GM. 2013. An easy-to-perform photometric assay for methyltransferase activity measurements. Anal. Biochem. 432:38-40. http://dx.doi.org/10.1016/j.ab.2012.09.026.
12. Quadri LE, Weinreb PH, Lei M, Nakano MM, Zuber P, Walsh CT. 1998. Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases. Biochemistry 37:1585-1595. http://dx.doi.org/10.1021/bi9719861.
13. Meluzzi D, Zheng WH, Hensler M, Nizet V, Dorrestein PC. 2008. Top-down mass spectrometry on low-resolution instruments: characterization of phosphopantetheinylated carrier domains in polyketide and non-ribosomal biosynthetic pathways. Bioorg. Med. Chem. Lett. 18: 3107-3111. http://dx.doi.org/10.1016/j.bmcl.2007.10.104.
14. Dorrestein PC, Bumpus SB, Calderone CT, Garneau-Tsodikova S, Aron ZD, Straight PD, Kolter R, Walsh CT, Kelleher NL. 2006. Facile detection of acyl and peptidyl intermediates on thiotemplate carrier domains via phosphopantetheinyl elimination reactions during tandem mass spectrometry. Biochemistry 45:12756-12766. http://dx.doi.org/10.1021/bi061169d.
15. Lohr F, Jenniches I, Fritzler M, Meehan MJ, Sylvester M, Schmitz A, Gütschow M, Dorrestein PC, König GM, Schäberle TF. 2013. A double bond migration in corallopyronin A biosynthesis. Chem. Sci. 4:4175-4180. http://dx.doi.org/10.1039/c3sc51854j.
16. Rix U, Fischer C, Remsing LL, Rohr J. 2002. Modification of post-PKS tailoring steps through combinatorial biosynthesis. Nat. Prod. Rep. 19: 542-580. http://dx.doi.org/10.1039/b103920m.
17. Müller I, Müller R. 2006. Biochemical characterization of MelJ and MelK. FEBSJ. 273:3768-3778. http://dx.doi.org/10.1111/j.1742-4658.2006. 05385.x.
18. Müller I, Weinig S, Steinmetz H, Kunze B, Veluthoor S, Mahmud T, Müller R. 2006. A unique mechanism for methyl ester formation via an amide intermediate found in myxobacteria. Chembiochem 7:1197-1205. http://dx.doi.org/10.1002/cbic.200600057.
19. De Baere I, Derua R, Janssens V, Van Hoof C, Waelkens E, Merlevede W, Goris J. 1999. Purification of porcine brain protein phosphatase 2A leucine carboxyl methyltransferase and cloning of the human homologue. Biochemistry 38:16539-16547. http://dx.doi.org/10.1021/bi991646a.
20. Kagan RM, Clarke S. 1994. Widespread occurrence of three sequence motifs in diverse S-adenosylmethionine-dependent methyltransferases suggests a common structure for these enzymes. Arch. Biochem. Biophys. 310:417-427. http://dx.doi.org/10.1006/abbi.1994.1187.
21. Sucipto H, Wenzel SC, Müller R. 2013. Exploring chemical diversity of pyrone antibiotics: molecular basis of myxopyronin biosynthesis. Chembiochem 14:1581-1589. http://dx.doi.org/10.1002/cbic.201300289.
22. Hitchman TS, Crosby J, Byrom KJ, Cox RJ, Simpson TJ. 1998. Catalytic self-acylation of type II polyketide synthase acyl carrier proteins. Chem. Biol. 5:35-47. http://dx.doi.org/10.1016/S1074-5521(98)90085-0.
23. Li S, Anzai Y, Kinoshita K, Kato F, Sherman DH. 2009. Functional analysis of MycE and MycF, two O-methyltransferases involved in the biosynthesis of mycinamicin macrolide antibiotics. Chembiochem 10: 1297-1301. http://dx.doi.org/10.1002/cbic.200900088.
24. Musiol EM, Härtner T, Kulik A, Moldenhauer J, Piel J, Wohlleben W, Weber T. 2011. Supramolecular templating in kirromycin biosynthesis: the acyltransferase KirCII loads ethylmalonyl-CoA extender onto a specific ACP of the trans-AT PKS. Chem. Biol. 18:438-444. http://dx.doi.org/10.1016/j.chembiol. 2011.02.007.
25. Dorrestein PC, Blackhall J, Straight PD, Fischbach MA, Garneau-Tsodikova S, Edwards DJ, McLaughlin S, Lin M, Gerwick WH, Kolter R, Walsh CT, Kelleher NL. 2006. Activity screening of carrier domains within nonribosomal peptide synthetases using complex substrate mixtures and large molecule mass spectrometry. Biochemistry 45:1537-1546. http://dx.doi.org/10.1021/bi052333k.