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were identified by running known standards through the same UHPLC-MS system to determine their retention times. Peaks from samples were matched to the retention times from known standards for identification. Heat maps were generated using the Multi Experiment Viewer program.MetaboLightsPublicHybrid Quadrupole-Orbitrap high resolution mass spectrometer (Q Exactive Orbitrap; Thermo Scientific)Samples were resuspended in 150 μl HPLC grade water (Fisher Optima) for analysis on a Thermo-Fisher Vanquish Horizon UHPLC joined to a hybrid quadrupole-Orbitrap high resolution mass spectrometer (Q Exactive Orbitrap; Thermo Scientific). Chromatography was performed using a 100 mm x 2.1 mm x 1.7 μm BEH C18 Acquity column (Waters) at 30 °C. 15 μl of sample was injected via an autosampler at 4 °C and flow rate was 200 μl/min. Solvent A was 97:3 water/methanol with 9 mM Acetate and 10 mM tributylamine (TBA) with a pH of 8.2 (Sigma-Aldrich). Solvent B was 100% methanol with no TBA (Sigma-Aldrich). Products were eluted in 95% A/5% B for 2.5 min, then a gradient of 95% A/5% B to 5% A/95% B over 14.5 min, then held for an additional 2.5 min at 5% A/95% B. Finally the gradient was returned to 95% A/5% B over 0.5 min, and held for 5 min to re-equilibrate the column.A profile of the joint Toxoplasma-host infection metabolome finds broad changes to metabolism and discovers a novel parasite metabolic capability. 10.1101/463075.William OlsonUniversity of Wisconsin Madisonforeskin fibroblastmass spectrometryHFF dishes in triplicate were infected with 2 x 10^6 tachyzoites, or mock infected with an equal addition of media by volume. At time points 1.5, 3, 6, 9, 12, 24, 36, and 48 hr post infection (HPI), dishes were washed 3x with ice cold PBS, then quenched with 80:20 HPLC grade Methanol:Water (Sigma-Aldrich). Dishes were incubated on dry ice in a −80 °C for 15 min. Plates were scraped, the solution removed and spun at 2500 x g for 5 min at 4 °C. The supernatant was removed and stored on ice, then the pellet was washed again in quenching solution and re-spun. Supernatants were combined, dried down under a N2 gas manifold, and stored at −80 °C.Homo sapiensRAW files were converted to mzXML files using the MassMatrix file conversion tool. Data analysis was performed using the Metabolomics Analysis and Visualization Engine (MAVEN) software[1]. </br></br> Ref:</br> [1] Melamud E, Vastag L, Rabinowitz JD. Metabolomic analysis and visualization engine for LC-MS data. Anal Chem. 2010 Dec 1;82(23):9818-26. doi:10.1021/ac1021166. PMID:21049934</br>Media Taurine AbundanceSBPase Expression in LysateGlucose-6-13C LabelingInfection StatusExogenous SBPaseExogenous BFPLysate TreatmentTaurine 15N Labelingwolson3@wisc.eduhttps://www.ebi.ac.uk/metabolights/MTBLS899Low passage type II ME49 Toxoplasma gondii was used in all experiments. Human Foreskin Fibroblasts (HFFs) from the ATCC were grown in 60 mm dishes in DMEM with 10% Fetal Bovine Serum (FBS), 2 mM L-glutamine, and 1% penicillin-streptomycin (Sigma-Aldrich). Once HFFs were in deep quiescence, defined as 10 days post confluency, DMEM media was changed to metabolomic media, RPMI1640 supplemented with 2 mM L-glutamine, 1% FBS dialyzed against PBS (MW cutoff of 10 kD), 10mM HEPEs, and 1% penicillin-streptomycin. After 35 hr, the media was again changed with metabolic media, 1 hr before infection with T. gondii.Metabolomicsultra-performance liquid chromatography-mass spectrometrysedoheptulose 7-phosphateToxoplasma gondiipentose-phosphate shunt, non-oxidative branchpentose-phosphate shunt, oxidative branchuntargeted metabolitessedoheptulose-bisphosphatase activitysedoheptulose 1,7-bisphosphatetranscriptomic dataultra-performance liquid chromatography-mass spectrometrysedoheptulose 7-phosphateToxoplasma gondiipentose-phosphate shunt, non-oxidative branchpentose-phosphate shunt, oxidative branchuntargeted metabolitessedoheptulose-bisphosphatase activitysedoheptulose 1,7-bisphosphatetranscriptomic dataMass spectra were collected on a hybrid quadrupole-Orbitrap high resolution mass spectrometer (Q Exactive Orbitrap; Thermo Scientific) by electrospray ionization (negative mode). Scan range was 75 to 1000 m/z.dGDPHydroxyphenylacetic acidCDP3-hydroxybutyryl-CoAThiamine pyrophosphateglucono-delta-lactonetrans,trans-farnesyl diphosphatethymidineglucose-1-phosphatefructose-1-6-bisphosphateKynurenic acidglutamateD-glucosamine-1-phosphateorotidine-5'-phosphateshikimateorotateFlavonecytidineN-carbamoyl-L-aspartateprephenateUDP-D-glucuronateGMPcoenzyme AadenosinedGTPcyclic-AMPdTMPdeoxyribose-phosphatedihydroxy-acetone-phosphateUDP-N-acetyl-glucosaminealpha-ketoglutarateGeranyl-PPasparagineallantoateornithinecytosineD-sedoheptulose-1-phosphatequinolinatealanine3-methylphenylacetic acidpropionyl-CoAOctulose 8-phosphatecitratephenylpyruvatedeoxyinosineFMNS-adenosyl-L-methioninamineMethylcysteinedCMP5-methyl-THFguanosinexanthine3-phosphoglyceratexanthosinelipoatelactateATPfumarate4-Pyridoxic acidindoleglutathione disulfidedUTPcysteineXanthurenic acidADP7-methylguanosinearginineIDPcystathionine2-Hydroxy-2-methylbutanedioic acidthiamineacetylphosphatemethylmalonyl-CoAIndoleacrylic acidleucineAminoadipic acidlysinefolatemethionineallantoinN-acetyl-L-ornithinePyrophosphateUMPtyrosinePhenyllactic acidN-acetyl-glutamateNADPHdTTPisocitrateglucosamine1-Methyl-HistidinesuccinatedTDPglucose-6-phosphateglycolatehomocysteinephenylalanineNADP+FADp-hydroxybenzoatedeoxyguanosinetrehaloseUric acidanthranilateglyoxylatepyruvateGuanidoacetic aciddAMPacetoacetyl-CoAAcetylcarnitinenicotinateCitraconic acidcarnitineuracilN-acetyl-glucosamine-6-phosphate3-hydroxy-3-methylglutaryl-CoAS-adenosyl-L-methioninethymineADP-D-glucoseinosineGTPAscorbic acid2-oxo-4-methylthiobutanoatesarcosinedCDPS-adenosyl-L-homocysteineCholic acidisoleucinemyo-inositolGDPhypoxanthineglycineCellobiosePhenylpropiolic acidD-gluconate2-Isopropylmalic acidCMP2,3-dihydroxybenzoic acidhomocysteic acidaconitatephosphoenolpyruvatedCTPribose-phosphateN-acetyl-glucosamine-1-phosphateD-glucono-delta-lactone-6-phosphatexanthosine-5-phosphateSedoheptoluse bisphosphatedephospho-CoAhydroxyprolineS-ribosyl-L-homocysteineD-glucosamine-6-phosphateN-acetyl-glutaminedeoxyadenosine4-aminobutyratedeoxyuridineglutamine2-dehydro-D-gluconateNADHpyridoxineS-methyl-5'-thioadenosinemalonyl-CoAPyroglutamic acidhexose-phosphateKynurenineUDP-D-glucoseOctulose BisphosphatepantothenatePyridoxaminetryptophanriboflavinthiamine-phosphateN-AcetylputrescinemethylnicotinamidedGMPD-sedoheptulose-7-phosphate2-keto-isovalerateN-Acetyl-L-alaninecyclic bis(3'->5') dimeric GMPglyceratehistidineNAD+fructose-6-phosphate3-S-methylthiopropionateserinedihydroorotateHydroxyisocaproic acidsn-glycerol-3-phosphateL-arginino-succinatetrehalose-6-PhosphateN-acetyl-glucosamineUTPhydroxyphenylpyruvatecholesteryl sulfate6-phospho-D-gluconateMethylmalonic acidshikimate-3-phosphateaspartateCDP-ethanolaminehomoserineAcetyllysine2,3-Diphosphoglyceric acidUDPAMP2-oxobutanoatebiotinoxaloacetatetaurinesucroseIMPprolineD-glyceraldehyde-3-phosphatemalateguaninedATP5-phosphoribosyl-1-pyrophosphateO-acetyl-L-serinecitrullinehistidinolD-glucarateOctulose 1-phosphatebutyryl-CoAadenosine 5'-phosphosulfateCDP-cholineglutathionep-aminobenzoateTaurodeoxycholic aciduridinesuccinyl-CoAguanosine 5'-diphosphate-3'-diphosphateD-erythrose-4-phosphateDeoxycholic acidIndole-3-carboxylic acidS-adenosyl-L-homoCysteineacetoacetateCarbamoyl phosphatethreonineadeninevalinedUMPacetyl-CoA3-phospho-serineCTPbiochemical pathways, host organism, Metabolic Process, joints, nucleocytoplasm, Product, determination, Glukose, Aminosaeure, Addresses, Metabolic Concepts, Infestations and Infections, Amino acid, Monohydrate, Embden-Meyerhof, Pentose, Profiles, (DL)-Isomer, Pentose Shunts, Pentose Phosphate Shunt, Embden Meyerhof Parnas Pathway, P'-5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, Pentosephosphate, Long Term, primary metabolites, Hexose Monophosphate Shunts, Carbon-12, Joint, Nicotinamide-Adenine, GRP1, Dextrose, Grp1, Pharmaceutical Product, Concepts, 1, Embden-Meyerhof Pathway, Metabolism Concept, Nicotinamide Adenine Dinucleotide Phosphate, Phenomenon, Effect, multicellular organismal biosynthetic process, Metabolic Profiles, sedoheptulose, C, single-organism biosynthetic process, amino acids, Man (Taxonomy), enzymes, catabolism, anabolism, PTPSTEP, Pathways, metabolic process resulting in cell growth, Phosphate, DL-glucose, Triphosphopyridine, medicine, Pharmaceutical, l(2)k08110, Carbon, biotransformation, s, Toxoplasmas, 3-di-(13)O-labeled, Infections and Infestations, Nucleotide, transcription from bacterial-type RNA polymerase promoter, Catabolism, Long-Term Effects, intracellular, inner salt, GPH, joint, Pathway, Process, Krebs cycle, Aminokarbonsaeure, metabolism resulting in cell growth, Modern, Longterm Effect, anaerobic glycolysis, dephosphorylation, Embden-Meyerhof-Parnas, Citric Acid, alpha-amino carboxylic acids, hexose monophosphate pathway, Vitreous, Embden-Meyerhof-Parnas Pathway, Shunt, Pentose-Phosphate Pathways, 3.1.3.48, secretion, Pentose Phosphate, Pharmaceutic, internal to cell, Tricarboxylic Acid Cycle, (alpha-D)-Isomer, NADPH, D-Glucose, Amino Acid, Acid, Amino acids, Step, CG11628, Adenosine 5'-(trihydrogen diphosphate), 6C, 2'-(dihydrogen phosphate), Pentose Phosphate Shunts, Infection and Infestation, Striatum-enriched protein-tyrosine phosphatase, Toxoplasma gondius, Krebs, Embden-Meyerhof pathway, Nicotinamide-Adenine Dinucleotide, Vitreous Carbon, Pentose-Phosphate, glycolysis, Parasite, D Glucose, Rib, STEP, Tricarboxylic Acid, bacterial transcription, metabolites, carbonium, Biocatalyst, Toxoplasma, Acids, Glucose Monohydrate, Embden-Meyerhof Pathways, humans, GRP1/cytohesin 1, Glucose, Effects, Processes, Biocatalysts, Aminocarbonsaeure, secondary metabolites, Pentosephosphate Shunts, carbon, Tricarboxylic Acid Cycles, biosynthesis, alpha-amino acid, Metabolic Processes, pentose phosphate shunt, Coenzyme II, Human, gondius, CG11633, cytohesin/GRP1, pentose-phosphate pathway, Homo sapiens, Metabolism, Krebs Cycle, Cycle, pentose phosphate pathway, modified Embden-Meyerhof pathway, Dinucleotide Phosphate, citric acid cycle, Hexose Monophosphate Shunt, Metabolism Phenomena, Metabolic Profile, Pentose-Phosphate Pathway, Man, protoplasm, Drugs, Cycles, Triphosphopyridine Nucleotide, protoplast, Longterm, formation, Metabolomes, nucleotide metabolism, Profile, Pentose Phosphate Pathways, l(2)SH2 0323, Metabolic Concept, Long-Term, clinical infection, Shunts, synthesis, Infestation and Infection, Kohlenstoff, Enzyme, drugs, Neural-specific protein-tyrosine phosphatase, Pentosephosphate Pathways, Pharmaceuticals., articular joint, Toxoplasma gondii, Long-Term Effect, Preparation, Anhydrous, Citric Acid Cycles, Pentosephosphate Shunt, Products, Embden Meyerhof Pathway, (beta-D)-Isomer, degradation, synthesize, drug, D-altro-2-heptulose, stepk, enzyme activity, alpha-amino acids, carbone, Concept, Metabolic Phenomena, carbono, Metabolism Concepts, oxidative TCA cycle, Long Term Effects, chemical analysis, Phenomena, Infection, metabolism, l(2)SH0323, Metabolic Phenomenon, CYH1, multicellular organism metabolic process, articulation, biodegradation, Metabolic, Pharmaceutic Preparations, metabolite, Pentose Shunt, Amino, Hexose Monophosphate, Embden-Meyerhof-Parnas pathway, Nicotinamide-Adenine Dinucleotide Phosphate, Anhydrous Dextrose, Longterm Effects, DmelCG11628, Carbon 12, Drug, Preparations, single-organism metabolic process, TCA cycle, D Ribose, Pentosephosphate Pathway, Modern Man, D-Ribose, assay, Pharmaceutical Products, Pharmaceutical Preparation, Glc, Anabolismbiochemical pathways, Parasite., joint, host organism, Metabolic Process, joints, wide/broad, degradation, Process, Processes, metabolism resulting in cell growth, Metabolic Concepts, Infestations and Infections, Profiles, broad, Metabolic Processes, Concept, Metabolic Phenomena, gondius, Metabolism Concepts, Joint, Metabolism, Phenomena, Infection, Concepts, secretion, Metabolism Concept, Phenomenon, Metabolic Profile, Metabolism Phenomena, metabolism, Metabolic Phenomenon, Metabolic Profiles, multicellular organism metabolic process, articulation, biodegradation, Metabolic, Metabolomes, catabolism, Profile, Metabolic Concept, Infection and Infestation, metabolic process resulting in cell growth, Toxoplasma gondius, clinical infection, Infestation and Infection, wide, single-organism metabolic process, articular joint, Toxoplasma, biotransformation, Toxoplasma gondii, Toxoplasmas, Infections and Infestations, Catabolism, AnabolismfalseA profile of the joint Toxoplasma-host infection metabolome finds broad changes to metabolism and discovers a novel parasite metabolic capabilityThe obligate intracellular parasite Toxoplasma gondii is auxotrophic for several key metabolites and must scavenge these, and carbon sources like glucose. from the host. While the importance of metabolism to Toxoplasma infection it obvious, it is unclear how Toxoplasma infection actually changes metabolism. To address this question, we measured changes in the joint host-parasite metabolome over a time course of infection. Host and parasite transcriptomes were simultaneously generated to measure changes in expression of metabolic enzymes that might correlate with changes in metabolite abundance. Toxoplasma infection changed metabolite abundance in multiple pathways, including the tricarboxylic acid cycle, the pentose phosphate pathway, glycolysis, amino acid synthesis, and nucleotide metabolism. Our analysis indicated that changes in some pathways, such as the tricarboxylic acid cycle, were mirrored by changes in parasite transcription, while changes in others, like the pentose phosphate pathway, were paired with changes in both the host and parasite transcriptomes. Further experiments led to the discovery of a Toxoplasma enzyme, sedoheptulose bisphosphatase, which funnels carbon into the pentose phosphate pathway through an energetically driven dephosphorylation reaction. This second route for ribose synthesis resolves a possible conflict between the Toxoplasma tricarboxylic acid cycle and pentose phosphate pathway, which are both NADP+ dependent. During periods of high energetic and ribose need, the competition for NADP+ could result in lethal redox imbalances. Sedoheptulose bisphosphatase represents a novel step in Toxoplasma central carbon metabolism that allows Toxoplasma to satisfy its ribose demand without using NADP+. Sedoheptulose bisphosphatase is not present in humans, highlighting its potential as a drug target.2019-05-102019-03-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:41321CHEBI:28834CHEBI:17407CHEBI:16359CHEBI:17211CHEBI:9410CHEBI:16494CHEBI:15467CHEBI:15517CHEBI:15531CHEBI:15539CHEBI:15345CHEBI:15351CHEBI:16497CHEBI:15380CHEBI:16625CHEBI:88356CHEBI:15346CHEBI:90355CHEBI:37050CHEBI:17633CHEBI:90333CHEBI:17111CHEBI:15468CHEBI:18077CHEBI:15996CHEBI:15422CHEBI:16284CHEBI:16474CHEBI:30851CHEBI:15713CHEBI:17625CHEBI:50392CHEBI:17720CHEBI:17677CHEBI:16311CHEBI:17621CHEBI:17200CHEBI:28862CHEBI:35825CHEBI:17808CHEBI:24809CHEBI:18344CHEBI:49537CHEBI:17405CHEBI:10072CHEBI:16908CHEBI:15751CHEBI:17552CHEBI:16761CHEBI:59783CHEBI:15641CHEBI:22211CHEBI:28635CHEBI:29888CHEBI:30769CHEBI:30887CHEBI:44897CHEBI:18009CHEBI:16666CHEBI:17659CHEBI:33574CHEBI:30744CHEBI:17969CHEBI:77854CHEBI:27470CHEBI:15999CHEBI:28846CHEBI:18026CHEBI:16675CHEBI:78682CHEBI:17050CHEBI:16264CHEBI:18075CHEBI:17709CHEBI:15842CHEBI:17239CHEBI:18012CHEBI:30754CHEBI:17052CHEBI:18066CHEBI:17489CHEBI:48928CHEBI:17626CHEBI:30915CHEBI:11851CHEBI:17533CHEBI:17858CHEBI:15652CHEBI:6650CHEBI:15350CHEBI:15859CHEBI:17015CHEBI:15584CHEBI:17672CHEBI:17713CHEBI:1438CHEBI:30860CHEBI:16027CHEBI:17013CHEBI:15940CHEBI:15741CHEBI:37574CHEBI:16192CHEBI:30831CHEBI:16119CHEBI:30763CHEBI:17345CHEBI:17202CHEBI:7916CHEBI:17622CHEBI:16695CHEBI:15918CHEBI:9532CHEBI:30753CHEBI:15846CHEBI:17361CHEBI:16108CHEBI:32816CHEBI:16742CHEBI:15811CHEBI:17256CHEBI:40992CHEBI:16856CHEBI:23634CHEBI:15344CHEBI:18107CHEBI:16010CHEBI:35581CHEBI:48153CHEBI:16891CHEBI:29052CHEBI:7125CHEBI:15784CHEBI:15978CHEBI:17268CHEBI:27897CHEBI:16077CHEBI:30865CHEBI:16680CHEBI:78697CHEBI:47878CHEBI:73685CHEBI:15414CHEBI:9082CHEBI:15721CHEBI:78320CHEBI:17497CHEBI:18283CHEBI:14314CHEBI:33508CHEBI:22652CHEBI:16217CHEBI:16732CHEBI:16436CHEBI:16938CHEBI:17775CHEBI:26562CHEBI:134365CHEBI:138395CHEBI:30837CHEBI:17748CHEBI:27469CHEBI:33198CHEBI:90324CHEBI:17172CHEBI:16335CHEBI:22660CHEBI:18237CHEBI:16750CHEBI:28997CHEBI:17057CHEBI:28044CHEBI:16450CHEBI:17596CHEBI:16708CHEBI:16235CHEBI:37024CHEBI:17821CHEBI:18186CHEBI:25017CHEBI:24898CHEBI:16344CHEBI:16709CHEBI:16704CHEBI:16811CHEBI:15956CHEBI:17562CHEBI:17712CHEBI:17368CHEBI:17568CHEBI:16551CHEBI:17992CHEBI:26271CHEBI:28300CHEBI:17981CHEBI:15356CHEBI:17755CHEBI:16543CHEBI:47987CHEBI:27625CHEBI:27570CHEBI:18257CHEBI:27266CHEBI:22653CHEBI:16040CHEBI:26986CHEBI:30653CHEBI:17230CHEBI:17822CHEBI:16449CHEBI:18211CHEBI:15676CHEBI:15891CHEBI:25094CHEBI:16255CHEBI:18385CHEBI:5417CHEBI:90364CHEBI:29016CHEBI:17768CHEBI:45658CHEBI:16410CHEBI:70958CHEBI:22193CHEBI:73024CHEBI:28683CHEBI:42491CHEBI:16002CHEBI:17126CHEBI:16865CHEBI:15428CHEBI:16238CHEBI:15625CHEBI:17509CHEBI:15682CHEBI:24741CHEBI:68440CHEBI:59640CHEBI:20794CHEBI:15611