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11101MCID_676f086566c932f78708ee2a 39381007 Wolfram Lorenzen[author] Lorenzen, Wolfram[Full Author Name] lorenzen, wolfram[Author] trying2...
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2352-3409572024DecData in briefData BriefUV-vis absorbance spectra, molar extinction coefficients and circular dichroism spectra for the two cyanobacterial metabolites anabaenopeptin A and anabaenopeptin B.11091411091411091410.1016/j.dib.2024.110914The UV-vis absorbance spectra, molar extinction coefficients and circular dichroism spectra, as well as NMR and high resolution tandem mass spectrometry spectra were determined for two prominent secondary metabolites from cyanobacteria, namely anabaenopeptin A and anabaenopeptin B. The compounds were extracted from the cyanobacterium Planktothrix rubescens CBT929 and purified by flash chromatography and HPLC. Exact amounts of isolated compounds were assessed by quantitative ¹H-NMR with internal calibrant ethyl 4-(dimethylamino)benzoate in DMSO‑d₆ at 298 K with a recycle delay (d1) of 120 s. UV-vis absorbance spectra were recorded in methanol at room temperature. Molar extinction coefficients were determined at 278 nm as 4190 M^-1 cm^-1 and 2300 M^-1 cm^-1 in methanol for anabaenopeptin A and anabaenopeptin B, respectively. Circular dichroism spectra and secondary fragmentation mass spectra are also reported.© 2024 The Authors. Published by Elsevier Inc.SteinerTillTDepartment of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.SchanbacherFranziskaFInstitut für Pharmazie, Freie Universität Berlin, Königin-Luise-Strasse 2+4, 14195 Berlin, Germany.LorenzenWolframWSimris Biologics GmbH, Magnusstrasse 11, 12489 Berlin, Germany.EnkeHeikeHSimris Biologics GmbH, Magnusstrasse 11, 12489 Berlin, Germany.JanssenElisabeth M-LEMSwiss Federal Institute of Aquatic Science and Technology (Eawag), Überlandstrasse 133, CH-8600 Düberndorf, Switzerland.NiedermeyerTimo H JTHJInstitut für Pharmazie, Freie Universität Berlin, Königin-Luise-Strasse 2+4, 14195 Berlin, Germany.GademannKarlKDepartment of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.engJournal Article20240915

NetherlandsData Brief1016549952352-3409CyanobacteriaMetabolitesQuantitative NMRUV–vis spectroscopy202452320248122024922024109730202410972920241094412024915epublish39381007PMC1146048510.1016/j.dib.2024.110914S2352-3409(24)00877-1Steiner T., Schanbacher F., Lorenzen W., Enke H., Janssen E.M.-L., Niedermeyer T.H.J., Gademann K. UV–vis absorbance spectra, molar extinction coefficients and circular dichroism spectra for the two cyanobacterial metabolites anabaenopeptin A and anabaenoepeptin B. Data Set. 2024 https://zenodo.org/records/11203432Beversdorf L.J., Weirich C.A., Bartlett S.L., Miller T.R. Variable cyanobacterial toxin and metabolite profiles across six eutrophic lakes of differing physiochemical characteristics. Toxins (Basel) 2017;9 doi: 10.3390/toxins9020062.10.3390/toxins9020062Miller T.R., Bartlett S.L., Weirich C.A., Hernandez J. Automated subdaily sampling of cyanobacterial toxins on a buoy reveals new temporal patterns in toxin dynamics. Environ. Sci. Technol. 2019;53:5661–5670. doi: 10.1021/acs.est.9b00257.10.1021/acs.est.9b0025731038305Janssen E.M.-L., Jones M.R., Pinto E., Dörr F., Torres M.A., Rios Jacinavicius F., Mazur-Marzec H., Szubert K., Konkel R., Tartaglione L., Dell'Aversano C., Miglione A., McCarron P., Beach D.G., Miles C.O., Fewer D.P., Sivonen K., Jokela J., Wahlsten M., Niedermeyer T.H.J., Schanbacher F., Leão P., Preto M., D'Agostino P.M., Baunach M., Dittmann E., Reher R. S75 | CyanoMetDB | Comprehensive database of secondary metabolites from cyanobacteria. Data Set. 2023 doi: 10.5281/ZENODO.7922070.10.5281/ZENODO.792207033765498Ferrinho S., Connaris H., Mouncey N.J., Goss R.J.M. Compendium of metabolomic and genomic datasets for cyanobacteria: mined the gap. Water Res. 2024;256 doi: 10.1016/j.watres.2024.121492.10.1016/j.watres.2024.12149238593604Itou Y., Suzuki S., Ishida K., Murakami M. Anabaenopeptins G and H, potent carboxypeptidase A inhibitors from the cyanobacterium Oscillatoria agardhii (NIES-595) Bioorg. Med. Chem. Lett. 1999;9:1243–1246. doi: 10.1016/S0960-894X(99)00191-2.10.1016/S0960-894X(99)00191-210340607Kodani S., Suzuki S., Ishida K., Murakami M. Five new cyanobacterial peptides from water bloom materials of lake Teganuma (Japan) FEMS Microbiol. Lett. 1999;178:343–348. doi: 10.1111/j.1574-6968.1999.tb08697.x.10.1111/j.1574-6968.1999.tb08697.xMurakami M., Suzuki S., Itou Y., Kodani S., Ishida K. New anabaenopeptins, carboxypeptidaze-A inhibitors from the cyanobacterium Aphanizomenon flos-aquae. J. Nat. Prod. 2000;63:1280–1282. doi: 10.1021/np000120k.10.1021/np000120k11000037Walther T., Renner S., Waldmann H., Arndt H.-D. Synthesis and structure-activity correlation of brunsvicamide-inspired cyclopeptide collection. ChemBioChem. 2009;10:1153–1162. doi: 10.1002/cbic.200900035.10.1002/cbic.20090003519360807Schreuder H., Liesum A., Lönze P., Stump H., Hoffmann H., Schiell M., Kurz M., Toti L., Bauer A., Kallus C., Klemke-Jahn C., Czech J., Kramer D., Enke H., Niedermeyer T.H.J., Morrison V., Kumar V., Brönstrup M. Isolation, co-crystallization and structure-based characterization of anabaenopeptins as highly potent inhibitors of activated thrombin activatable fibrinolysis inhibitor (TAFIa) Sci. Rep. 2016;6 doi: 10.1038/srep32958.10.1038/srep32958PMC501510627604544Blom J.F., Robinson J.A., Jüttner F. High grazer toxicity of [D-Asp3,(E)-Dhb7]microcystin-RR of Planktothrix rubescens as compared to different microcystins. Toxicon. 2001;39:1923–1932. doi: 10.1016/S0041-0101(01)00178-7.10.1016/S0041-0101(01)00178-711600156Harada K.-I., Matsuura K., Suzuki M., Watanabe M.F., Oishi S., Dahlem A.M., Beasley V.R., Carmichael W.W. Isolation and characterization of the minor components associated with mycrocystins LR and RR in the cyanobacterium (blue-green algae) Toxicon. 1990;28:55–64. doi: 10.1016/0041-0101(90)90006-S.10.1016/0041-0101(90)90006-S2109908Honkanen R.E., Zwiller J., Moore R.E., Daily S.L., Khatra B.S., Dukelow M., Boynton A.L. Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases. J. Biol. Chem. 1990;265:19401–19404. doi: 10.1016/S0021-9258(17)45384-1.10.1016/S0021-9258(17)45384-12174036Sano T., Kaya K. Two new (E)-2-amino-2-butenoic acid (Dhb)-containing microcystins isolated from Oscillatoria agardhii. Tetrahedron. 1998;54:463–470. doi: 10.1016/S0040-4020(97)10291-5.10.1016/S0040-4020(97)10291-5Weber M., Hellriegel C., Rück A., Sauermoser R., Wüthrich J. Using high-performance quantitative NMR (HP-qNMR®) for certifying traceable and highly accurate purity values of organic reference materials with uncertainties <0.1 % Accredit. Qual. Assur. 2013;18:91–98. doi: 10.1007/s00769-012-0944-9.10.1007/s00769-012-0944-9Harada K.-I., Fujii K., Shimada T., Suzuki M., Sano H., Adachi K., Carmichael W.W. Two cyclic peptides, anabaenopeptins, a third group of bioactive compounds from the cyanobacterium Anabaena flos-aquae NRC 525-17. Tetrahedron Lett. 1995;36:1511–1514. doi: 10.1016/0040-4039(95)00073-L.10.1016/0040-4039(95)00073-LAndersen R.A. Elsevier Academic Press; 2005. Algal Culturing Techniques.324640612021081020210810

1520-60258362020Jun26Journal of natural productsJ Nat ProdPrecursor-Directed Biosynthesis and Fluorescence Labeling of Clickable Microcystins.196019701960-197010.1021/acs.jnatprod.0c00251Microcystins, cyclic nonribosomal heptapeptides, are the most well-known cyanobacterial toxins. They are exceptionally well studied, but open questions remain concerning their physiological role for the producing microorganism or their suitability as lead compounds for anticancer drug development. One means to study specialized metabolites in more detail is the introduction of functional groups that make a compound amenable for bioorthogonal, so-called click reactions. Although it was reported that microcystins cannot be derivatized by precursor-directed biosynthesis, we successfully used this approach to prepare clickable microcystins. Supplementing different azide- or terminal alkyne containing amino acid analogues into the cultivation medium of microcystin-producing cyanobacteria strains, we found that these strains differ strongly in their substrate acceptance. Exploiting this flexibility, we generated more than 40 different clickable microcystins. We conjugated one of these derivatives with a fluorogenic dye and showed that neither incorporation of the unnatural amino acid analogue nor attachment of the fluorescent label significantly affects the cytotoxicity against cell lines expressing the human organic anion transporting polypeptides 1B1 or 1B3. Using time-lapse microscopy, we observed that the fluorescent microcystin is rapidly taken up into eukaryotic cells expressing these transporters.MoschnyJuliaJDepartment of Pharmaceutical Biology/Pharmacognosy, Institute of Pharmacy, University of Halle-Wittenberg, 06120 Halle (Saale), Germany.Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, 72076 Tübingen, Germany.LorenzenWolframWCyano Biotech GmbH, 12489 Berlin, Germany.HilferAlexandraACyano Biotech GmbH, 12489 Berlin, Germany.EckenstalerRobertRDepartment of Clinical Pharmacy and Pharmacotherapy, Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg, 06120 Halle (Saale), Germany.JahnsStefanSCyano Biotech GmbH, 12489 Berlin, Germany.EnkeHeikeHCyano Biotech GmbH, 12489 Berlin, Germany.EnkeDanDCyano Biotech GmbH, 12489 Berlin, Germany.SchneiderPhilippPInterfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, 72076 Tübingen, Germany.BenndorfRalf ARADepartment of Clinical Pharmacy and Pharmacotherapy, Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg, 06120 Halle (Saale), Germany.NiedermeyerTimo H JTHJ0000-0003-1779-7899Department of Pharmaceutical Biology/Pharmacognosy, Institute of Pharmacy, University of Halle-Wittenberg, 06120 Halle (Saale), Germany.Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, 72076 Tübingen, Germany.engJournal ArticleResearch Support, Non-U.S. Gov't20200528

United StatesJ Nat Prod79068820163-38640Amino Acids0Antibiotics, Antineoplastic0Azides0Fluorescent Dyes0Liver-Specific Organic Anion Transporter 10Microcystins0SLCO1B1 protein, human0SLCO1B3 protein, human0Solute Carrier Organic Anion Transporter Family Member 1B3IMAmino AcidschemistryAntibiotics, AntineoplasticchemistrypharmacologyAzideschemistryCell Line, TumorCyanobacteriachemistrymetabolismFluorescent DyesHEK293 CellsHumansLiver-Specific Organic Anion Transporter 1drug effectsMicrocystinsbiosynthesischemistryMicrocystischemistrymetabolismMolecular StructureSolute Carrier Organic Anion Transporter Family Member 1B3drug effects202052960202181160202052960ppublish3246406110.1021/acs.jnatprod.0c00251267476492016060720161126

0006-3002186132016MarBiochimica et biophysica actaBiochim Biophys ActaIdentification of a triacylglycerol lipase in the diatom Phaeodactylum tricornutum.239248239-4810.1016/j.bbalip.2015.12.023S1388-1981(15)00245-0Diatoms accumulate triacylglycerols (TAGs) as storage lipids, but the knowledge about the molecular mechanisms of lipid metabolism is still sparse. Starting from a partial sequence for a putative TAG-lipase of the diatom Phaeodactylum tricornutum retrieved from the data bases, we have identified the full length coding sequence, tgl1. The gene encodes an 813 amino acid sequence that shows distinct motifs for so called "true" TAG-lipases [EC 3.1.1.3] that have been functionally characterized in model organisms like Arabidopsis thaliana and Saccharomyces cerevisiae. These lipases mediate the first initial step of TAG breakdown from storage lipids. To test whether Tgl1 can act as a TAG-lipase, a His-tagged version was overexpressed in Escherichia coli and the protein indeed showed esterase activity. To identify the TAG degrading function of Tgl1 in P. tricornutum, knock-down mutant strains were created using an antisense RNA approach. In the mutant cell lines the relative tgl1-mRNA-level was reduced up to 20% of that of the wild type, accompanied by a strong increase of TAG in the lipid extracts. In spite of the TAG accumulation, the polar lipid species pattern appeared to be unchanged, confirming the TAG-lipase function of Tgl1.Copyright © 2016 Elsevier B.V. All rights reserved.BarkaFrederikFPlant Cell Physiology, Institute of Molecular Biosciences, Goethe University Frankfurt, Max-von-Laue-Straße 9, Biozentrum, 60438 Frankfurt am Main, Germany.AngstenbergerMaxMPlant Cell Physiology, Institute of Molecular Biosciences, Goethe University Frankfurt, Max-von-Laue-Straße 9, Biozentrum, 60438 Frankfurt am Main, Germany.AhrendtTilmanTMerck Stiftungsprofessur für Molekulare Biotechnologie, Institute of Molecular Biosciences, Goethe University Frankfurt, Max-von-Laue-Straße 9, Biozentrum, 60438 Frankfurt am Main, Germany.LorenzenWolframWMerck Stiftungsprofessur für Molekulare Biotechnologie, Institute of Molecular Biosciences, Goethe University Frankfurt, Max-von-Laue-Straße 9, Biozentrum, 60438 Frankfurt am Main, Germany.BodeHelge BHBMerck Stiftungsprofessur für Molekulare Biotechnologie, Institute of Molecular Biosciences, Goethe University Frankfurt, Max-von-Laue-Straße 9, Biozentrum, 60438 Frankfurt am Main, Germany; Buchmann Institute for Molecular Life Sciences (BMLS), Goethe University Frankfurt, Max-von-Laue-Straße 15, 60438 Frankfurt am Main, Germany.BüchelClaudiaCPlant Cell Physiology, Institute of Molecular Biosciences, Goethe University Frankfurt, Max-von-Laue-Straße 9, Biozentrum, 60438 Frankfurt am Main, Germany. Electronic address: c.buechel@bio.uni-frankfurt.de.engJournal ArticleResearch Support, Non-U.S. Gov't20151230

NetherlandsBiochim Biophys Acta02175130006-30020RNA, Antisense0Recombinant Proteins0TriglyceridesEC 3.1.1.3LipaseIMAmino Acid MotifsAmino Acid SequenceDiatomsenzymologygeneticsGene Expression Regulation, EnzymologicGene Knockdown TechniquesGenotypeHydrolysisKineticsLipasechemistrygeneticsmetabolismMolecular Sequence DataPhenotypePhylogenyRNA, AntisensegeneticsmetabolismRecombinant ProteinsmetabolismTriglyceridesmetabolismAntisenseLipaseLipidsPolyunsaturated fatty acids2015330201512172015122920161106020161106020166960ppublish2674764910.1016/j.bbalip.2015.12.023S1388-1981(15)00245-0253844832015022520181113

1098-553019722015JanJournal of bacteriologyJ BacteriolNonacetogenic growth of the acetogen Acetobacterium woodii on 1,2-propanediol.382391382-9110.1128/JB.02383-14Acetogenic bacteria can grow by the oxidation of various substrates coupled to the reduction of CO2 in the Wood-Ljungdahl pathway. Here, we show that growth of the acetogen Acetobacterium woodii on 1,2-propanediol (1,2-PD) as the sole carbon and energy source is independent of acetogenesis. Enzymatic measurements and metabolite analysis revealed that 1,2-PD is dehydrated to propionaldehyde, which is further oxidized to propionyl coenzyme A (propionyl-CoA) with concomitant reduction of NAD. NADH is reoxidized by reducing propionaldehyde to propanol. The potential gene cluster coding for the responsible enzymes includes genes coding for shell proteins of bacterial microcompartments. Electron microscopy revealed the presence of microcompartments as well as storage granules in cells grown on 1,2-PD. Gene clusters coding for the 1,2-PD pathway can be found in other acetogens as well, but the distribution shows no relation to the phylogeny of the organisms.Copyright © 2015, American Society for Microbiology. All Rights Reserved.SchuchmannKaiKMolecular Microbiology & Bioenergetics, Institute of Molecular Biosciences, Johann Wolfgang Goethe University, Frankfurt am Main, Germany.SchmidtSilkeSMolecular Microbiology & Bioenergetics, Institute of Molecular Biosciences, Johann Wolfgang Goethe University, Frankfurt am Main, Germany.Martinez LopezAntonioAMolecular Microbiology & Bioenergetics, Institute of Molecular Biosciences, Johann Wolfgang Goethe University, Frankfurt am Main, Germany.KaberlineChristinaCMolecular Microbiology & Bioenergetics, Institute of Molecular Biosciences, Johann Wolfgang Goethe University, Frankfurt am Main, Germany.KuhnsMartinMMolecular Microbiology & Bioenergetics, Institute of Molecular Biosciences, Johann Wolfgang Goethe University, Frankfurt am Main, Germany.LorenzenWolframWMerck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe University, Frankfurt am Main, Germany.BodeHelge BHBMerck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe University, Frankfurt am Main, Germany Buchmann Institute for Molecular Life Sciences (BMLS), Johann Wolfgang Goethe University, Frankfurt am Main, Germany.JoosFriederikeFMax-Planck-Institut für Biophysik, Strukturbiologie, Frankfurt am Main, Germany.MüllerVolkerVMolecular Microbiology & Bioenergetics, Institute of Molecular Biosciences, Johann Wolfgang Goethe University, Frankfurt am Main, Germany vmueller@bio.uni-frankfurt.de.engJournal ArticleResearch Support, Non-U.S. Gov't20141110

United StatesJ Bacteriol2985120R0021-91936DC9Q167V3Propylene GlycolIMAcetobacteriumgrowth & developmentmetabolismultrastructurePropylene Glycolmetabolism20141112602014111260201522660201571ppublish25384483PMC427258410.1128/JB.02383-14JB.02383-14Drake HL, Gößner AS, Daniel SL. 2008. Old acetogens, new light. Ann N Y Acad Sci 1125:100–128. doi:10.1196/annals.1419.016.10.1196/annals.1419.01618378590Müller V. 2003. Energy conservation in acetogenic bacteria. Appl Environ Microbiol 69:6345–6353. doi:10.1128/AEM.69.11.6345-6353.2003.10.1128/AEM.69.11.6345-6353.2003PMC26230714602585Ragsdale SW, Pierce E. 2008. Acetogenesis and the Wood-Ljungdahl pathway of CO2 fixation. Biochim Biophys Acta 1784:1873–1898. doi:10.1016/j.bbapap.2008.08.012.10.1016/j.bbapap.2008.08.012PMC264678618801467Wood HG, Ragsdale SW, Pezacka E. 1986. The acetyl-CoA pathway of autotrophic growth. 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1539-726255122014DecJournal of lipid researchJ Lipid ResA comprehensive insight into the lipid composition of Myxococcus xanthus by UPLC-ESI-MS.262026332620-3310.1194/jlr.M054593Analysis of whole cell lipid extracts of bacteria by means of ultra-performance (UP)LC-MS allows a comprehensive determination of the lipid molecular species present in the respective organism. The data allow conclusions on its metabolic potential as well as the creation of lipid profiles, which visualize the organism's response to changes in internal and external conditions. Herein, we describe: i) a fast reversed phase UPLC-ESI-MS method suitable for detection and determination of individual lipids from whole cell lipid extracts of all polarities ranging from monoacylglycerophosphoethanolamines to TGs; ii) the first overview of a wide range of lipid molecular species in vegetative Myxococcus xanthus DK1622 cells; iii) changes in their relative composition in selected mutants impaired in the biosynthesis of α-hydroxylated FAs, sphingolipids, and ether lipids; and iv) the first report of ceramide phosphoinositols in M. xanthus, a lipid species previously found only in eukaryotes.Copyright © 2014 by the American Society for Biochemistry and Molecular Biology, Inc.LorenzenWolframWMerck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe-Universität Frankfurt, D-60438 Frankfurt am Main, Germany.BozhüyükKenan A JKAMerck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe-Universität Frankfurt, D-60438 Frankfurt am Main, Germany.CortinaNiña SNSCluster of Excellence Macromolecular Complexes, Johann Wolfgang Goethe-Universität Frankfurt, D-60438 Frankfurt am Main, Germany Buchmann Institute for Molecular Life Sciences (BMLS), Johann Wolfgang Goethe-Universität Frankfurt, D-60438 Frankfurt am Main, Germany.BodeHelge BHBMerck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe-Universität Frankfurt, D-60438 Frankfurt am Main, Germany Buchmann Institute for Molecular Life Sciences (BMLS), Johann Wolfgang Goethe-Universität Frankfurt, D-60438 Frankfurt am Main, Germany.engJournal ArticleResearch Support, Non-U.S. Gov't20141020

United StatesJ Lipid Res03766060022-22750Bacterial Proteins0LipidsIMBacterial ProteinsgeneticsChromatography, High Pressure LiquidChromatography, Reverse-PhaseDatabases, ChemicalGas Chromatography-Mass SpectrometryLipid MetabolismLipidsanalysischemistryMetabolomicsmethodsMolecular StructureMutationMyxococcus xanthusmetabolismSpectrometry, Mass, Electrospray IonizationTandem Mass Spectrometryceramide phosphoinositolselectrospray ionization-mass spectrometryether lipidslipid profileslipidomicsmyxobacteriareversed phaseultra-performance liquid chromatography2014102260201410226020151020602015121ppublish25332432PMC424245410.1194/jlr.M054593S0022-2275(20)36701-8Kaiser D. 2008. Myxococcus—from single-cell polarity to complex multicellular patterns. Annu. Rev. Genet. 42: 109–130.18605899Weissman K. J., Müller R. 2010. Myxobacterial secondary metabolites: bioactivities and modes-of-action. Nat. Prod. Rep. 27: 1276–1295.20520915Kearns D. B., Shimkets L. J. 2001. Lipid chemotaxis and signal transduction in Myxococcus xanthus. Trends Microbiol. 9: 126–129.11239790Ring M. W., Schwär G., Thiel V., Dickschat J. S., Kroppenstedt R. M., Schulz S., Bode H. B. 2006. Novel iso-branched ether lipids as specific markers of developmental sporulation in the myxobacterium Myxococcus xanthus. J. Biol. Chem. 281: 36691–36700.16990257Bhat S., Ahrendt T., Dauth C., Bode H. B., Shimkets L. J. 2014. Two lipid signals guide fruiting body development of Myxococcus xanthus. MBio. 5: e00939–e009313.PMC395052624520059Fautz E., Rosenfelder G., Grotjahn L. 1979. Iso-branched 2- and 3-hydroxy fatty acids as characteristic lipid constituents of some gliding bacteria. J. Bacteriol. 140: 852–858.PMC216725118159Bode H. B., Ring M. W., Kaiser D., David A. C., Kroppenstedt R. M., Schwär G. 2006. Straight-chain fatty acids are dispensable in the myxobacterium Myxococcus xanthus for vegetative growth and fruiting body formation. J. 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1552-44691062014JunNature chemical biologyNat Chem BiolA multifunctional enzyme is involved in bacterial ether lipid biosynthesis.425427425-710.1038/nchembio.1526Fatty acid-derived ether lipids are present not only in most vertebrates but also in some bacteria. Here we describe what is to our knowledge the first gene cluster involved in the biosynthesis of such lipids in myxobacteria that encodes the multifunctional enzyme ElbD, which shows similarity to polyketide synthases. Initial characterization of elbD mutants in Myxococcus xanthus and Stigmatella aurantiaca showed the importance of these ether lipids for fruiting body formation and sporulation.LorenzenWolframWMerck-Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe-Universität Frankfurt, Frankfurt, Germany.AhrendtTilmanTMerck-Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe-Universität Frankfurt, Frankfurt, Germany.BozhüyükKenan A JKAMerck-Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe-Universität Frankfurt, Frankfurt, Germany.BodeHelge BHBMerck-Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Johann Wolfgang Goethe-Universität Frankfurt, Frankfurt, Germany.engGENBANKKJ633122KJ633123KJ633124KJ633125Journal ArticleResearch Support, Non-U.S. Gov't20140511

United StatesNat Chem Biol1012319761552-44500Ethers0Lipids0Multifunctional EnzymesIMCatalytic DomainEthersGenes, BacterialGenome, BacterialLipidsbiosynthesischemistryMolecular Sequence DataMultifunctional EnzymesgeneticsphysiologyMultigene FamilyMyxococcus xanthusenzymologygeneticsphysiologySpores, BacterialphysiologyStigmatella aurantiacaenzymologygeneticsphysiology20139142014414201451360201451360201471660ppublish2481467310.1038/nchembio.1526nchembio.1526J Am Chem Soc. 2010 Aug 11;132(31):10628-920230003Can J Biochem Physiol. 1959 Aug;37(8):911-713671378Nature. 1970 Aug 15;227(5259):680-55432063Anal Biochem. 1984 Apr;138(1):141-36731838J Bacteriol. 2004 Jul;186(13):4361-815205438J Bacteriol. 2007 Dec;189(24):8793-80017905977Biochimie. 2013 Jan;95(1):59-6522771767Chem Biol. 2004 Feb;11(2):195-20115123281Mol Microbiol. 2009 Oct;74(2):497-51719788540Chem Biol. 1996 Nov;3(11):923-368939709J Biol Chem. 2006 Dec 1;281(48):36691-70016990257J Bacteriol. 1951 Sep;62(3):293-30014888646Food Chem. 2013 Jan 15;136(2):464-7123122085Folia Microbiol (Praha). 2012 Sep;57(5):463-7222763737Environ Microbiol. 2006 Nov;8(11):1935-4917014493Int J Syst Evol Microbiol. 2009 Jun;59(Pt 6):1524-3019502347J Bacteriol. 1998 Mar;180(6):1425-309515909Proc Natl Acad Sci U S A. 2001 Nov 20;98(24):13990-411717456Biochem Cell Biol. 1990 Jan;68(1):225-302350489Angew Chem Int Ed Engl. 2012 Nov 26;51(48):12086-923097192Conserv Biol. 2013 Feb;27(1):197-20923110546J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jan 5;814(1):155-6115607720J Bacteriol. 1978 Feb;133(2):763-8415048J Biol Chem. 2002 Sep 6;277(36):32768-7412084727Proc Natl Acad Sci U S A. 2013 Oct 29;110(44):17790-524127586Chem Phys Lipids. 2011 Jul;164(5):315-4021635876Mol Plant. 2013 Mar;6(2):246-923253604BMC Bioinformatics. 2010 Jan 27;11:5720105319Biochim Biophys Acta. 2011 Mar;1811(3):186-9321195206Appl Environ Microbiol. 2000 Mar;66(3):884-910698746FEBS Lett. 1976 Mar 15;63(1):107-111261671230971922013080720121121

1521-377351482012Nov26Angewandte Chemie (International ed. in English)Angew Chem Int Ed EnglReciprocal cross talk between fatty acid and antibiotic biosynthesis in a nematode symbiont.120861208912086-910.1002/anie.201205384BrachmannAlexander OAOMolekulare Biotechnologie, Institut für Molekulare Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue-Str. 9, 60438 Frankfurt am Main, Germany.ReimerDanielaDLorenzenWolframWAugusto AlonsoEduardoEKoppYannickYPielJörnJBodeHelge BHBengJournal ArticleResearch Support, Non-U.S. Gov't20121024

GermanyAngew Chem Int Ed Engl03705431433-78510Anti-Bacterial Agents0Fatty AcidsIMAnimalsAnti-Bacterial AgentsbiosynthesischemistryFatty AcidsbiosynthesischemistryNematodametabolism2012782012102660201210266020138860ppublish2309719210.1002/anie.201205384229542272012100220220410

1754-6834512012Sep06Biotechnology for biofuelsBiotechnol BiofuelsCytosolic re-localization and optimization of valine synthesis and catabolism enables inseased isobutanol production with the yeast Saccharomyces cerevisiae.6565The branched chain alcohol isobutanol exhibits superior physicochemical properties as an alternative biofuel. The yeast Saccharomyces cerevisiae naturally produces low amounts of isobutanol as a by-product during fermentations, resulting from the catabolism of valine. As S. cerevisiae is widely used in industrial applications and can easily be modified by genetic engineering, this microorganism is a promising host for the fermentative production of higher amounts of isobutanol.Isobutanol production could be improved by re-locating the valine biosynthesis enzymes Ilv2, Ilv5 and Ilv3 from the mitochondrial matrix into the cytosol. To prevent the import of the three enzymes into yeast mitochondria, N-terminally shortened Ilv2, Ilv5 and Ilv3 versions were constructed lacking their mitochondrial targeting sequences. SDS-PAGE and immunofluorescence analyses confirmed expression and re-localization of the truncated enzymes. Growth tests or enzyme assays confirmed enzymatic activities. Isobutanol production was only increased in the absence of valine and the simultaneous blockage of the mitochondrial valine synthesis pathway. Isobutanol production could be even more enhanced after adapting the codon usage of the truncated valine biosynthesis genes to the codon usage of highly expressed glycolytic genes. Finally, a suitable ketoisovalerate decarboxylase, Aro10, and alcohol dehydrogenase, Adh2, were selected and overexpressed. The highest isobutanol titer was 0.63 g/L at a yield of nearly 15 mg per g glucose.A cytosolic isobutanol production pathway was successfully established in yeast by re-localization and optimization of mitochondrial valine synthesis enzymes together with overexpression of Aro10 decarboxylase and Adh2 alcohol dehydrogenase. Driving forces were generated by blocking competition with the mitochondrial valine pathway and by omitting valine from the fermentation medium. Additional deletion of pyruvate decarboxylase genes and engineering of co-factor imbalances should lead to even higher isobutanol production.BratDawidDInstitute of Molecular Biosciences, Goethe-University Frankfurt, Max-von-Laue-Str, 9, 60438, Frankfurt am Main, Germany. e.boles@bio.uni-frankfurt.de.WeberChristianCLorenzenWolframWBodeHelge BHBBolesEckhardEengJournal Article20120906

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1521-37651882012Feb20Chemistry (Weinheim an der Bergstrasse, Germany)ChemistryDetermination of the absolute configuration of peptide natural products by using stable isotope labeling and mass spectrometry.234223482342-810.1002/chem.201103479Structure elucidation of natural products including the absolute configuration is a complex task that involves different analytical methods like mass spectrometry, NMR spectroscopy, and chemical derivation, which are usually performed after the isolation of the compound of interest. Here, a combination of stable isotope labeling of Photorhabdus and Xenorhabdus strains and their transaminase mutants followed by detailed MS analysis enabled the structure elucidation of novel cyclopeptides named GameXPeptides including their absolute configuration in crude extracts without their actual isolation.Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.BodeHelge BHBInstitut für Molekulare Biowissenschaften, Molekulare Biotechnologie, Goethe Universität Frankfurt, Max-von-Laue-Strasse 9, 60436 Frankfurt am Main, Germany. h.bode@bio.uni-frankfurt.deReimerDanielaDFuchsSebastian WSWKirchnerFerdinandFDauthChristinaCKeglerCarstenCLorenzenWolframWBrachmannAlexander OAOGrünPeterPengJournal ArticleResearch Support, Non-U.S. Gov't20120120

GermanyChemistry95137830947-65390Biological Products0Peptides0Peptides, CyclicIMBiological ProductschemistryIsotope LabelingmethodsMagnetic Resonance SpectroscopyMass SpectrometrymethodsPeptideschemistryPeptides, CyclicchemistryStereoisomerism2011114201212460201212460201251060ppublish2226680410.1002/chem.201103479196173622009091720211020

1098-5530191182009SepJournal of bacteriologyJ BacteriolIsoprenoids are essential for fruiting body formation in Myxococcus xanthus.584958535849-5310.1128/JB.00539-09It was recently shown that Myxococcus xanthus harbors an alternative and reversible biosynthetic pathway to isovaleryl coenzyme A (CoA) branching from 3-hydroxy-3-methylglutaryl-CoA. Analyses of various mutants in these pathways for fatty acid profiles and fruiting body formation revealed for the first time the importance of isoprenoids for myxobacterial development.LorenzenWolframWMolekulare Biotechnologie, Institut für Molekulare Biowissenschaften, Biozentrum/Campus Riedberg, Goethe Universität Frankfurt, Max-von-Laue-Str. 9, 60438 Frankfurt am Main, Germany.RingMichael WMWSchwärGertrudGBodeHelge BHBengJournal ArticleResearch Support, Non-U.S. Gov't20090717

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1520-60257212009JanJournal of natural productsJ Nat ProdMyxotyrosides A and B, Unusual rhamnosides from Myxococcus sp.828682-610.1021/np8005875Myxobacteria are gliding bacteria of the delta-subdivision of the Proteobacteria and known for their unique biosynthetic capabilities. Two examples of a new class of metabolites, myxotyrosides A (1) and B (2), were isolated from a Myxococcus sp. The myxotyrosides have a tyrosine-derived core structure glycosylated with rhamnose and acylated with unusual fatty acids such as (Z)-15-methyl-2-hexadecenoic and (Z)-2-hexadecenoic acid. The fatty acid profile of the investigated Myxococcus sp. (strain 131) is that of a typical myxobacterium with a high similarity to those described for M. fulvus and M. xanthus, with significant concentrations of neither 15-methyl-2-hexadecenoic acid nor 2-hexadecenoic acid being detected.OhlendorfBirgitBInstitute of Pharmaceutical Biology, UniVersity of Bonn, Nussallee 6, D-53115 Bonn, Germany.LorenzenWolframWKehrausStefanSKrickAnjaABodeHelge BHBKönigGabriele MGMengJournal Article

United StatesJ Nat Prod79068820163-38640Antineoplastic Agents0Fatty Acids0Glycolipids0myxotyroside A0myxotyroside BQN34XC755ARhamnoseIMAnimalsAntineoplastic Agentschemistryisolation & purificationpharmacologyBacillus megateriumdrug effectsChlorelladrug effectsDrug Screening Assays, AntitumorEscherichia colidrug effectsEurotiumdrug effectsFatty AcidsgeneticsGas Chromatography-Mass SpectrometryGlycolipidschemistryisolation & purificationpharmacologyMicrobial Sensitivity TestsMolecular StructureMyxococcuschemistryPlasmodium falciparumdrug effectsPseudomonas putidadrug effectsQuorum SensingRhamnoseanalogs & derivativeschemistryisolation & purificationpharmacology20081231902008123190200922090ppublish1911389410.1021/np800587510.1021/np8005875trying2...
Publications by Wolfram Lorenzen | LitMetric

Publications by authors named "Wolfram Lorenzen"

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UV-vis absorbance spectra, molar extinction coefficients and circular dichroism spectra for the two cyanobacterial metabolites anabaenopeptin A and anabaenopeptin B.

Till Steiner Franziska Schanbacher Wolfram Lorenzen Heike Enke Elisabeth M-L Janssen

Data Brief

December 2024

The UV-vis absorbance spectra, molar extinction coefficients and circular dichroism spectra, as well as NMR and high resolution tandem mass spectrometry spectra were determined for two prominent secondary metabolites from cyanobacteria, namely anabaenopeptin A and anabaenopeptin B. The compounds were extracted from the cyanobacterium CBT929 and purified by flash chromatography and HPLC. Exact amounts of isolated compounds were assessed by quantitative H-NMR with internal calibrant ethyl 4-(dimethylamino)benzoate in DMSO‑ at 298 K with a recycle delay (d1) of 120 s.

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Precursor-Directed Biosynthesis and Fluorescence Labeling of Clickable Microcystins.

Julia Moschny Wolfram Lorenzen Alexandra Hilfer Robert Eckenstaler Stefan Jahns

J Nat Prod

June 2020

Microcystins, cyclic nonribosomal heptapeptides, are the most well-known cyanobacterial toxins. They are exceptionally well studied, but open questions remain concerning their physiological role for the producing microorganism or their suitability as lead compounds for anticancer drug development. One means to study specialized metabolites in more detail is the introduction of functional groups that make a compound amenable for bioorthogonal, so-called click reactions.

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Identification of a triacylglycerol lipase in the diatom Phaeodactylum tricornutum.

Frederik Barka Max Angstenberger Tilman Ahrendt Wolfram Lorenzen Helge B Bode

Biochim Biophys Acta

March 2016

Diatoms accumulate triacylglycerols (TAGs) as storage lipids, but the knowledge about the molecular mechanisms of lipid metabolism is still sparse. Starting from a partial sequence for a putative TAG-lipase of the diatom Phaeodactylum tricornutum retrieved from the data bases, we have identified the full length coding sequence, tgl1. The gene encodes an 813 amino acid sequence that shows distinct motifs for so called "true" TAG-lipases [EC 3.

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Nonacetogenic growth of the acetogen Acetobacterium woodii on 1,2-propanediol.

Kai Schuchmann Silke Schmidt Antonio Martinez Lopez Christina Kaberline Martin Kuhns Wolfram Lorenzen

J Bacteriol

January 2015

Acetogenic bacteria can grow by the oxidation of various substrates coupled to the reduction of CO2 in the Wood-Ljungdahl pathway. Here, we show that growth of the acetogen Acetobacterium woodii on 1,2-propanediol (1,2-PD) as the sole carbon and energy source is independent of acetogenesis. Enzymatic measurements and metabolite analysis revealed that 1,2-PD is dehydrated to propionaldehyde, which is further oxidized to propionyl coenzyme A (propionyl-CoA) with concomitant reduction of NAD.

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A comprehensive insight into the lipid composition of Myxococcus xanthus by UPLC-ESI-MS.

Wolfram Lorenzen Kenan A J Bozhüyük Niña S Cortina Helge B Bode

J Lipid Res

December 2014

Analysis of whole cell lipid extracts of bacteria by means of ultra-performance (UP)LC-MS allows a comprehensive determination of the lipid molecular species present in the respective organism. The data allow conclusions on its metabolic potential as well as the creation of lipid profiles, which visualize the organism's response to changes in internal and external conditions. Herein, we describe: i) a fast reversed phase UPLC-ESI-MS method suitable for detection and determination of individual lipids from whole cell lipid extracts of all polarities ranging from monoacylglycerophosphoethanolamines to TGs; ii) the first overview of a wide range of lipid molecular species in vegetative Myxococcus xanthus DK1622 cells; iii) changes in their relative composition in selected mutants impaired in the biosynthesis of α-hydroxylated FAs, sphingolipids, and ether lipids; and iv) the first report of ceramide phosphoinositols in M.

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A multifunctional enzyme is involved in bacterial ether lipid biosynthesis.

Wolfram Lorenzen Tilman Ahrendt Kenan A J Bozhüyük Helge B Bode

Nat Chem Biol

June 2014

Fatty acid-derived ether lipids are present not only in most vertebrates but also in some bacteria. Here we describe what is to our knowledge the first gene cluster involved in the biosynthesis of such lipids in myxobacteria that encodes the multifunctional enzyme ElbD, which shows similarity to polyketide synthases. Initial characterization of elbD mutants in Myxococcus xanthus and Stigmatella aurantiaca showed the importance of these ether lipids for fruiting body formation and sporulation.

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Reciprocal cross talk between fatty acid and antibiotic biosynthesis in a nematode symbiont.

Alexander O Brachmann Daniela Reimer Wolfram Lorenzen Eduardo Augusto Alonso Yannick Kopp

Angew Chem Int Ed Engl

November 2012

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Cytosolic re-localization and optimization of valine synthesis and catabolism enables inseased isobutanol production with the yeast Saccharomyces cerevisiae.

Dawid Brat Christian Weber Wolfram Lorenzen Helge B Bode Eckhard Boles

Biotechnol Biofuels

September 2012

Background: The branched chain alcohol isobutanol exhibits superior physicochemical properties as an alternative biofuel. The yeast Saccharomyces cerevisiae naturally produces low amounts of isobutanol as a by-product during fermentations, resulting from the catabolism of valine. As S.

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Determination of the absolute configuration of peptide natural products by using stable isotope labeling and mass spectrometry.

Helge B Bode Daniela Reimer Sebastian W Fuchs Ferdinand Kirchner Christina Dauth Wolfram Lorenzen

Chemistry

February 2012

Structure elucidation of natural products including the absolute configuration is a complex task that involves different analytical methods like mass spectrometry, NMR spectroscopy, and chemical derivation, which are usually performed after the isolation of the compound of interest. Here, a combination of stable isotope labeling of Photorhabdus and Xenorhabdus strains and their transaminase mutants followed by detailed MS analysis enabled the structure elucidation of novel cyclopeptides named GameXPeptides including their absolute configuration in crude extracts without their actual isolation.

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Isoprenoids are essential for fruiting body formation in Myxococcus xanthus.

Wolfram Lorenzen Michael W Ring Gertrud Schwär Helge B Bode

J Bacteriol

September 2009

It was recently shown that Myxococcus xanthus harbors an alternative and reversible biosynthetic pathway to isovaleryl coenzyme A (CoA) branching from 3-hydroxy-3-methylglutaryl-CoA. Analyses of various mutants in these pathways for fatty acid profiles and fruiting body formation revealed for the first time the importance of isoprenoids for myxobacterial development.

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Myxotyrosides A and B, Unusual rhamnosides from Myxococcus sp.

Birgit Ohlendorf Wolfram Lorenzen Stefan Kehraus Anja Krick Helge B Bode

J Nat Prod

January 2009

Myxobacteria are gliding bacteria of the delta-subdivision of the Proteobacteria and known for their unique biosynthetic capabilities. Two examples of a new class of metabolites, myxotyrosides A (1) and B (2), were isolated from a Myxococcus sp. The myxotyrosides have a tyrosine-derived core structure glycosylated with rhamnose and acylated with unusual fatty acids such as (Z)-15-methyl-2-hexadecenoic and (Z)-2-hexadecenoic acid.

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