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Metabolic pathways poster
- 1. 2H+ H+ OXALOACETATE PYRUVATE SUCCINYL-CoA GLUTARATE CITRATE MALATE 2-OXO- ASPARTATE NO2 - NO3 - N2 NH4 CH3COSCoA ACETYL-CoA HOH CO2 NAD TRANSA M INATION 2H+ 2H + + CO2 5-Amino- levulinate Glycine H+ H+ H+ H+ H+ H+ c H+ H+a F0 F1 F1 β2 1α β α γ 10 c-sub-units AD P+ Pi a H+ 3.6.1.34 H +-transporting ATP synth ase α δ F6 oscp ATP ADP +Pi FUMARATE UQH2 UQ UQH2 NADH+H+ CH2COO- C(OH)COO- CH2COO- CH(OH)COO- CHCOO- CH2COO- -OOCCOCH2CH2COO- -OOCCH2CH2CO.SCoA -OOCCOCH2COO- CH3CH(OH)CH2CO.SCoA -OOCCH=CHCOO- CCCC Glyoxylate Cycle -OOCCHO GTP GDPATP + HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen 5-Amino- levulinate COO- CH2 CH2 H2NCH2C=O FADH2 FADCyt.b Fe-S SUCCINATE II CH3COCOO- PYRUVATE Pi X Y Cyt.c1 Fe-S 2e- 2e- 1e- 1e- III 2UQ UQ UQH22UQH2 2UQ. _ UQ. _ Cyt.bL Cyt.bH Cyt.c IV CuA CuB CuA 1.9.3.1 2e- Heme a Heme a3 2H+ 2H+4H+ 4H+ 2H+ NAD+ NADH+H+ NAD+ 1.1.1.39 1.2.4.1 2.3.1.12 3.1.3.43 4.1.1.32 4.1.3.7 4.2.1.3 1.1.1.41 1.2.4.2 2.3.1.61 6.2.1.4 -OOCCH2CH2COO- 1.3.5.1 4.2.1.2 1.1.1.37 6.4.1.1 4.1.3.8 4.1.3.1 4.1.3.2 ISOCITRATE 2.6.1.1 2.3.1.16 4.1.1.71 1.2.1.16 5.1.99.1 5.4.99.2 4.3.1.1 1.4.1.2 1.4.1.14 6.3.5.4 1.6.6.1 1.7.99.4 1.7.7.1 1.6.6.4 1.18.6.1 2.3.1.37 1.10.2.2 1.10.2.2 γ εδ β H++ 33 β AT P ADP ENDERGONIC REACTION 1.6.5.3 I FMNH2 FMN I 1.6. 5.3 2Fe -S (5 Clusters) H+ H+ H+ H+ ATP 4H+ 2H+ 2H+ or H+ PHOTO- SYSTEM l O2 3.6.1.34 NADP+ Glyceraldehyde Ribulose-1,5-bis-P 2β 88 H+ c 32 ε a 32 α1 α ε α β2 1 3 α α β 3 α β H+ H+ H+ H+ H+H+ H+ H+ H+H+ H+H+H+H+ H+ H+ H+H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+H+ H+H+ H+H+H+ Translocated protons H+ H+ H+ H+ Pi Ferredoxin 4H+ PC PC PC PQH2 2PQH2 PQ _ . 2PQ _ . Fe-S Cyt.f PQ 2PQ Cyt bf 2e- 1e- 1e- 2e- 2e- 2e- 2e- Cyclic Photophosphorylation PQ PHOTO- SYSTEM II Cyt bc Non-cyclic electron flo w 2e- 2e- Mn 2e- * Protons from Water H2O H+ H+ 2H+ 2H+ γ ATP synthase CO2 Fixation H+ ADPPi H+ NADPH+H+ eee ATPTHYLAKOID MEMBRANE CHLOROPLAST OUTER MEMBRANE THYLAKOID LUMEN STROMA (electric current) P680 Chl.a QA QB Pheophytin P700 Chl.A0 A1 Fe-S ATP ADP ATP 1/2O2 H2O PQH2 To Brain - A M I N O A C I D S P Y R I M I D I N E S P U R I N E S C A T E C H O L A M I N E S A R O M A T I C A M I N O A C I D S hv VISION L I P I D P H O T O S Y N T H E S I S P O R P H Y R I N S S T E R O I D S I S O P R E N O I D S P H O S P H O L I P I D S D E G R A D A T I O N L I P I D B I O S Y N T H E S I S P E N T O S E S H E X O S E S P O L Y S A C C H A R I D E S COCH CH(NH )COO2 3 + FOLIC ACID C1 POOL VALINE ATP ATP 4.1.1.4 1.1.1.30 CH COCH3 3 CH COCH COO3 2 CH CH(OH)CH COO3 2 3-OH-ButyrateAcetone Acetoacetate KETONE BODIES HYALURONIC ACID DERMATAN BLOOD GROUP SUBSTANCES PEPTIDO- GLYCAN N-Ac-Neuraminate (Sialate) UDP- Iduronate UDP-N-Ac- Galactosamine UDP- Galacturonate GDP-Fucose TDP-Rhamnose ADP- Glucose UDP-Glucose TDP-4-Oxo- 6-deoxyglucose MANNOSE CHITIN CHONDROITIN PECTIN ALGINATES INULIN CELLULOSE O-ANTIGENS STARCH GLYCOGEN LACTOSE GALACTOSE O OH HO OH OH CH3 O OPPT O OH OH O OH ACNH HO OH O OHHO OPPU NHAC OH OH OH OH HO OH NHCOCH OH HO O OPPG CH OH2 HO P UDP-N-Ac- Glucosamine pyruvate N-Ac-Mannosamine-6-P UDP-Glucuronate GDP-Mannose N-Ac-Mannosamine UDP-N-Ac-Glucosamine N-Ac-Glucosamine-6-P Sorbitol Fructose-1-P Erythrose-4-P 3-Dehydrogulonate L-Xylose L-Lyxose D-Xylulose D-Ribose Ribitol L-Arabitol L-Xylulose L-Ribulose L-Ribulose-5-P L-Xylulose-5-P L-Arabinose Xylitol D-Xylose D-Arabinose D-Ribulose ASCORBATE 2, 3-Dioxogulonate N-Ac-Glucosamine-1-P Inositol-PInositolGlucuronateGulonate Gulonolactone 2-Oxogulonolactone Fructose 6-P-Gluconate D-Ribulose-5-P D-Xylulose-5-P Mannose-1-P GDP-Glucose TDP-Glucose UDP-Galactose Galactose-P Glucose-1-P Glucose-6-P Fructose-6-P Fructose- 1:6-bis-P OH H H H O HOCH2 C C C C CO OH OHH OH H H O HOCH2 C C C CO CO OHH H OH H C C OH CO P-Ribosyl amine Glycerate 2, 3-Diphospho- glycerate 3-P-Glyceraldehyde 1:3-bis-P-Glycerate 3-P-Glycerate 2-P-Glycerate P-enolpyruvate Inositol CH OH2 CH OH2 HOCH CH OH2 CH O2 HOCH P Glycerol UDP-Galactose UDP-Sugars CH CH OH3 2 ETHANOL Dihydroxy- acetone-P (Glycerone-P) Glucosamine-6-P Phospho- serine Chain elongation Mitochondrial Serine Serine Indole-3-glycerol-P 3-Deoxy-D-arabino- heptulosonate-7-P Indoleacetate (Auxin) Indoxyl Formylkynurenine Kynurenine 3-Hydroxy kynurenine 3-Hydroxy anthranilate 2-Amino-3-carboxy muconate semialdehyde NH OH Tryptamine 1-(o-Carboxy phenylamino) 1-deoxyribulose-5-P N-(5-P-Ribosyl) anthranilate Anthranilate Catechol NH Indole- acetaldehyde NH CH CHO2 Indolepyruvate N H C-CH(OH)CH(OH)CH O2 P CH 2-Aminomuconate- 6-semialdehyde CH CH NH2 2 2 NH 1.2.3.7 4.1.1.43 3.5.1.9 3.7.1.3 4.2.1.20 1.13.11.6 4.1.1.45 2.4.2.18 4.6.1.4 4.1.1.48 1.14.13.9 4.6.1.3 Dehydro- quinate 4.2.1.10 1.1.1.25 2.5.1.19 Shikimate-3-P Shikimate-5 enolpyruvate 3-P Chorismate PEP 2.7.1.71 1.4.1.19 Homogentisate Phenylpyruvate Cinnamate Coumarate Prephenate 2-Amino muconate Fumarate Aspartate GLYCINE Sarcosine Hydroxy- pyruvate P-Hydroxy- pyruvate SERINE Imidazole glycerol-P P-Ribosyl-ATP P-Ribosylformimino 5-aminoimidazole- carboxamide-R P Formimino glutamate Imidazolone propionate Urocanate Cystathionine Homocysteine Phosphoadenylyl- sulphate (PAPS) CH (NH )COOH2 3 + Histidinol-PHistidinolHistidinal 3.1.3.15 2.6.1.91.1.1.23 3.6.1.31 5.3.1.162.4.2.17 Asparagine ALANINE 3-Sulphinyl pyruvate Oxobutyrate 2-Aceto-2- hydroxy- butyrate O-Phospho- homoserine HO SCH CH NH2 2 2 2 Hypotaurine HO SCH CH NH3 2 2 2 Taurine Glutamate γ-Glutamylcysteine Glutathione Glycine Cysteine ß-Alanine Cysteate S-Adenosyl homocysteine 4.2.99.2 1.1.1.86 4.2.1.9 1.1.1.86 4.2.1.9 2.6.1.32 4.1.3.18 S-Adenosyl methionine (SAM) 2-Methylaceto- acetyl-CoA 2-Acetolactate 2-3-Dihydroxy isovalerate 2-Oxo- isovalerate 3-Hydroxy- isobutyrate 3-Hydroxy- Isobutyryl-CoA Methyl acrylyl-CoA 2-Methyl-3- hydroxy- butyryl-CoA Tiglyl-CoA 2 Methylbutyryl- CoA 2:3-Di-OH- 3-methylvalerate 2-Oxo-3-methyl valerate Isobutyryl-CoA Cysteine sulphinate 4.2.99.9 2-Isopropyl- malate CH CH COCOO3 2 + CH CH(NH )COO3 3 CH CH(OH)COO3 HO SCH COCOO2 2 OCH COCOO2P OCH CH(NH )COO2 3P HOCH COCOO2 HOCH CH(NH )COO2 3 + + OH CH COCOO2 COO OH OH O COO OH OH HO P COO OH OH O CH2 P COO O-C-COO OH O OH OOC CH COCOO2 N H HOC-CH(OH)CH(OH)CH 2OP CH COO NH2 COO OH NH2COO COO OCH OOCCH NHCH2 3 CH (CH ) COS-ACP3 2 14 CH (CH ) COSCoA3 2 14 CH (CH ) CH=CHCO-S-ACP3 2 2 CH CH=CHCO-S-ACP3 CH CH(OH)CH COS-ACP3 2 COSCoA Linoleate Oleoyl-CoA Stearoyl-CoA Dehydrostearoyl-CoA OH-Stearoyl-CoA Oxostearoyl-CoA Palmitoyl-ACP Palmitoyl-CoA ACYL-ACP 2, 3-Enoyl-ACP 3, 4-Decenoyl-ACP 2, 3-Decenoyl-ACP 3-OH-Acyl-ACP 3-Oxoacyl-ACP 3-Oxo-Decanoyl-ACP 3-Oxo-Hexanoyl-ACP3-OH-Hexanoyl-ACP2, 3-Hexenoyl-ACP Butanoyl-ACP Crotonoyl-ACP 3-OH-Butanoyl-ACP Acetoacetyl-ACP Hexanoyl-ACP 3-OH-Decanoyl-ACPDecanoyl-ACP Palmitoleoyl-ACP γ-Linolenate Arachidonate Leukotriene B4 COSCoA CO-S-ACP Thromboxane B2 HOOCCH CO-S-ACP2 Malonyl-ACP HOOCCH CO-SCoA2 Malonyl-Co-A CH CO-S-ACP3 Acetyl-ACP CH O-CO-R2 CH OH2 R’-CO-OCH FATTY ACID ACYL-CoA (Cytosol) CH O-CO-R2 CH O2 R’-CO-OCH P Cardiolipin Phosphatidylglycerol Acetylcholine Glycerophosphocholine Lysolecithin Choline plasmalogen CDP-choline Choline-P Mevaldate CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2 Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine Acyl-CoA Acyl-CoA Cerebroside GalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2 NHCOR Isopentenyl-PP (C5) Dimethylallyl-PP (C5) Geranyl-geranyl-PP (C20) Farnesyl-PP (C15) Squalene (C30) Geranyl-PP (C10) Desmosterol Zymosterol Lanosterol CH C = CHCH O3 2 PP CH3 Ceramide Gangliosides NHCOR CH O2 PP OPP CH2 CHOLESTEROL CH C(OH)CH CH OH3 2 2 CH COO2 CH C(OH)CH CHO3 2 CH COO2 NADP+ Dehydroascorbate OH H O HOCH2 C C C C CO OHH OH OH H O HOCH2 C C CO CO CO H NAD+ Pi ADPADP Phytoene (C40) Lycopene (C40) ß-CAROTENE (C40) RhodopsinMetarhodopsin Retinoate trans-Retinal 11-cis-Retinoltrans-Retinol (Vitamin A) Retinol esters Dark Light Ubiquinone (Coenzyme Q) Menaquinone Plastoquinone Phylloquinone (Vitamin K) Opsin CHO CH OH2 CHO CH OH2 CH3CH O3 CH O3 n O O O O Phytol (C20) α-Tocopherol (Vitamin E) Quinolinate Quinolinate- nucleotide Nicotinate- nucleotide Desamino-NAD 5-Hydroxy- tryptophan 5-Hydroxytryptamine (SEROTONIN) N-Acetyl-5-O-methyl-serotonin (MELATONIN) NH CH CH NHCOCH2 2 3HO NH CH CH NHCOCH2 2 3CH O3 + NAD( P) NICOTINATE N-Acetyl-serotonin 2.4.2.19 Dopamine Dopa Dopaquinone THYROXINEMELANIN OH OH CHOHCH NHCH2 3 OH OH CHOHCH NH2 2 4-OH-3-Methoxy- phenylglycol CHOHCH NH2 2 OH OCH3OCH3 CHOHCH OH2 OH OCH3 4-OH-3-Methoxy- D-mandelate Cyclic AMP ATP Dephospho-Coenzyme A 4-P-Pantetheine 4-P-Pantothenylcysteine 4-P-Pantothenate Pantoate 6.3.2.1 1.1.1.169 3.5.1.22 2.7.1.33 NH NH O O O O CH OH2 OH OCH3 CH(OH)COO H2 NH3 + CH-COO CO O COO NRibose- P N + COO NH CH COO2 O OH CH O2 P NHCOCH NH2 2 OH Formyl glycinamide-R P Urea Formyl glycinamidine-R P Allantoate Allantoin URATE ADP Xanthine Hypoxanthine Inosine Adenine Adenylo- succinate 5-Amino imidazole-R P 5-Amino-4-imidazole carboxylate-R P 5-Amino-4-imidazole (N-succinylcarboxamide)-R P 5-Aminoimidazole carboxamide-R P Formylamido- imidazole- carboxamide-R P H NCONH2 2 HN H C2 CHO NH RP NH C C C O C CO OC NH NH H N HN H C C O C CH OC NH N N HN Carbamoyl ß-alanine Dihydro- uracil Uracil d-ADP d-ATP GTP GDP XANTHOSINE-P (XMP) TTP TDP ß-Ureido isobutyrate Dihydro thymine Thymine d-UMP d-CMP d-CDP CDP Carbamoyl aspartate Dihydro orotate Orotate Orotidine-P Uridine-P (UMP) UDP 3-Amino- isobutyrate CH C NH2 CHOC NH NCH C O CHOC N H HN CH-CH3 C O OC NH HN CH2 CH2 CH2 C O OC NH HN C O CHOC NH HN C CH3 Methylmalonyl semialdehyde OHCCHCOO CH3 CH2 C O CH-COOOC NH HN CH C O C-COOOC NH HN H NCONHCH CH COO2 2 2 C C C CH RP HC NH NH OOC-CH-CH COO2 N N N CHO NH RP NH OC H C2 2.7.7.43 3.1.3.29 1.1.1.158 5.1.3.13 2.7.1.38 3.2.1.23 3.1.3.29 4.1.3.20 2.7.1.60 5.1.3.14 5.1.3.7 5.1.3.1 2.7.1.4 5.4.2.3 3.1.1.17 1.1.1.49 1.1.1.21 2.7.7.23 3.1.3.251.13.99.11.1.1.19 1.1.3.8 5.3.1.3 2.7.1.53 1.1.1.9 2.7.1.15 2.7.1.17 5.1.3.4 5.1.3.1 2.2.1.2 4.1.2.13 2.7.1.11 2.7.1.47 2.2.1.1 1.2.1.12 1.1.1.29 1.1.1.95 1.3.1.35 1.14.99.25 2.3.1.41 2.3.1.41 2.3.1.41 1.1.1.100 5.3.99.5 4.2.1.60 5.3.99.3 1.14.99.1 1.13.11.34 1.3.1.10 1.3.1.9 1.14.99.5 1.3.1.9 4.2.1.61 4.2.1.60 4.2.1.60 4.2.1.59 4.2.1.58 1.3.1.9 1.3.1.9 6.2.1.3 3.1.2.20 1.1.1.100 5.3.1.1 HOOC-COOH Oxalate Glycolate HOCH CHO2 Glycol aldehyde Ethanolamine-P 2.7.1.30 2.3.1.7 3.7.1.2 4.1.3.5 2.7.8.8 2.1.1.17 2.1.1.71 1.3.1.35 2.7.8.2 3.1.4.3 3.1.4.4 2.7.7.15 3.1.1.5 3.1.4.2 2.7.1.32 2.7.1.82 1.2.4.1 2.3.1.12 1.8.1.4 2.6.1.2 1.4.1.1 4.1.1.1 2.3.1.50 1.1.1.102 3.1.4.12 2.7.8.3 2.4.1.62 3.2.1.46 5.2.1.3 1.2.1.36 2.3.1.76 3.1.1.21 5.2.1.7 5.4.99.7 1.14.99.7 4.3.1.8 4.2.1.75 4.1.1.371.3.3.31.3.3.4 4.99.1.1 2.5.1.29 2.4.1.47 4.1.1.28 2.3.1.5 2.1.1.4 6.3.5.1 6.3.1.5 2.4.2.11 2.7.7.18 2.6.1.5 1.2.1.32 1.13.11.5 2.1.1.28 2.1.2.2 6.3.3.1 3.5.2.5 1.4.1.10 1.7.3.3 1.1.1.204 1.1.3.22 1.1.3.22 4.1.1.28 4.1.1.21 2.1.2.3 2.4.2.1 1.5.99.2 2.1.1.5 2.6.1.22 3.5.2.3 2.6.1.51 1.4.1.7 3.1.3.3 2.6.1.52 2.1.3.2 ACETATE 2.4.2.4 2.1.1.45 RP CH C O CHOC N HN 1.3.1.14 2.4.2.10 4.1.1.23 2.7.7.7 2.7.7.7 2.7.7.7 1.17.4.1 2.7.7.7 2.7.4.14 4.4.1.1 1.6.4.1 1.13.11.20 4.4.1.8 4.2.1.22 1.1.1.27 4.1.1.29 6.3.2.3 6.3.2.2 1.8.1.3 LACTATE Acetaldehyde 2.7.1.24 2.7.7.3 4.1.1.36 Bile Acids CH CH COSCoA3 2 Propanoyl-CoA 1.1.1.31 2.1.3.1 4.1.1.41 5.1.99.1 6.4.1.3 6.3.2.5 2.1.1.14 2.1.1.13 4.6.1.1 CDP-Ethanolamine 1.1.1.35 4.2.1.17 + HO SCH CH(NH )COO2 2 3 3.5.2.7 NHHN CH OOC CHCH CH COO2 2 CMP-N-Acetyl neuraminate CDP-diacyl glycerol CHOLINE Ethanolamine Glyoxylate HISTAMINE 2.3.1.46 Homoserine Tyramine Plant PigmentsTannins Maleyl acetoacetate Fumaryl acetoacetate 5.2.1.2 CH COO2 OH OH OH CH CH NH2 2 2 OH OH CH CH NH2 2 2 Hydroxyphenyl pyruvate α-Tocopherol (Vitamin E) LIGNIN d-GTP OH OH OH O HO OH P OPPT CH3 HO OHOH O NADPH 2.2.1.1 2.7.1.3 1.1.1.45 1.1.1.130 1.10.3.3 1.10.2.1 1.1.1.10 ATP CH CH NH2 2 2 NH HO 5.4.99.5 1.14.16.12.6.1.51.13.11.27 Indole 4.1.99.1 1.13.11.11 OH O OH NH C C CH CH O2 P H HCOO NH2 COO 6.3.5.3 6.3.2.6 4.3.2.2 Guanine DNA 6.3.4.44.3.2.2 C C O C CH HC NH N N HN C C O C CH HC NH N N HN 3.5.3.4 2.4.2.1 2.7.7.62.7.7.6 2.7.7.6 2.7.7.6 2.7.4.6 2.7.4.3 2.7.4.4 2.7.4.6 2.4.2.15 1.1.1.205 6.3.4.1 6.3.5.2 2.7.4.4 3.5.4.3 3.2.2.2 2.4.2.1 3.1.3.5 3.1.4.6 6.3.4.2 1.17.4.1 1.17.4.1 3.5.4.12 2.7.4.8 2.7.4.9 2.7.4.6 2.4.2.4 1.3.1.2 3.5.2.23.5.1.6 3.5.1.6 3.5.2.2 3.5.4.1 Diphospho- mevalonate Mevalonate 3-Oxopentanoyl-CoA 3-Oxoacyl-CoA3-OH-Acyl-CoA2, 3-Enoyl-CoA 2, 3-Hexenoyl-CoA 3-OH-Hexanoyl-CoA Acetoacetyl-CoA3-OH-Butanoyl-CoACrotonoyl-CoA Pentanoyl-CoA 3-OH-Pentanoyl-CoA 1.1.1.35 1.1.1.35 1.1.1.157 1.3.99.3 1.3.99.3 1.3.99.2 1.1.1.35 Odd C Fatty acids Succinylhomoserine CO2 2-OXO ACID Glutamyl-P Glutamine UREA P-CreatineCreatine Creatinine Glycine CITRULLINE Glutamic semialdehyde 2-AMINO ACID Pyrroline-5- carboxylate GlyoxylatePyruvate 4-Hydroxy- 2-oxoglutarate 4-Hydroxy- glutamate 3-Hydroxy- pyrroline- 5-carboxylate Putrescine H NCH CH CH CH NH2 2 2 2 2 2 Spermidine Spermine N -Trimethyllysine66 N -Trimethyl- 3-OH-lysine Carnitine Glutaryl-CoA Saccharopine2-Aminoadipate semialdehyde 2-Aminoadipate2-Oxoadipate Arginino- succinate Guanidoacetate Methylmalonyl-CoA 4.1.2.12 Aspartyl Semialdehyde 2, 3-Dihydro- dipicolinate 1.2.1.11 4.2.1.52 1.3.1.26 Piperideine- 2, 6-dicarboxylate N-Succinyl- 2-amino-6-oxo- pimelate 2.6.1.17 N-Succinyl-2, 6 diaminopimelate Diamino- pimelate 3.5.1.18 3-Methyl- glutaconyl-CoA (CH ) CHCH COSCoA3 2 2(CH ) CHCH COSCoA3 2 2 3-Methyl- crotonyl-CoA Isovaleryl-CoA OxopantoateHCHO OOCCH C = CHCOSCoA2 CH3 CH COCHCOSCoA3 CH3 CH CH=CHCOSCoA3 CH3 CH CH(OH)CHCOSCoA3 CH3 C(OH)CH(OH)COO CH CH3 2 CH3 CH = CCOSCoA2 CH3 HOCH CHCOS-CoA-2 CH3 CH CHCO-SCoA3 CH3 C (OH)CH(OH)COO CH3 CH3 CH CH CHCOSCoA3 2 CH3 CH C = CHCOSCoA3 CH3 ATP 4-Aminobutyrate (GABA) 1.3.99.7 1.5.1.2 1.14.11.2 2.6.1.39 1.2.1.31 1.14.11.8 2.5.1.16 2.5.1.22 4.1.3.16 2.6.1.23 1.5.99.8 1.5.1.2 6.4.1.4 1.3.99.10 4.2.1.33 2.6.1.6 1.1.1.85 Oxoleucine COOH (CH ) CHCHCH(OH)COO3 2 S-Adenosylmethyl thiopropylamine (Decarboxylated SAM) PROLINE Coenzyme A CH C= CHCH3 2 CH3 O CH CH 3 3 HO CH3CH3 CH3 CH C-CH H O3 2 2C PP CH2 CH C= CHCH O2 2 PP CH3 3-P-Glycerol Phosphatidyl ethanolamine CEPHALIN 3.1.4.12 2.7.8.3 Progesterone 1.5.1.12 2.7.3.2 4.2.1.173.1.2.4 2.6.1.32 4.4.1.15 Acetylserine 2.7.7.42.7.1.251.8.99.1 Adenylylsulphate (APS) 2.7.1.39 4.4.1.15 4.1.1.29 4.2.99.8 2.3.1.30 P-Ribosyl-PP 1.1.1.1 1.2.1.4 Aspartyl-P 5.1.1.7 2.7.1.40 4.1.3.18 4.1.3.18 1.5.1.9 1.14.11.1 CHOLINE 2.1.1.13 1.3.1.2 NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P ADP- NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2 P-ADP- NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2 1.4.1.8 1.3.99.3 1.3.99.3 1.4.1.9 4.2.1.18 4.1.1.20 1.3.99.7 1.8.99.2 + CH CO-OCH CH(NH )COO2 2 3 2.5.1.6 2.1.1.10 2.1.1.20 1.1.1.3 1.1.1.3 4.2.1.18 4.1.2.5 4.3.1.5 4.2.1.20 2.1.2.1 2.1.1.20 Glyoxylate 2.1.1.6 1.4.3.4 1.14.18.1 1.14.16.2 Hexanoyl-CoA Butanoyl-CoA 6.3.4.16 6.3.5.5 2.7.2.11 2.1.3.3 NO 1.14.13.39 3.5.3.63.5.3.1 4.3.2.1 4.1.1.17 2.7.7.41 2.6.1.4 1.1.1.100 1.1.1.8 2.3.1.51 2.3.1.15 2.7.8.5 SO - 4 2 1.14.16.4 NH2OOC OOC 4.1.1.25 1.3.1.13 1.3.1.13 2.7.4.6 CYTIDINE- triphosphate (CTP) Cytosine 2.4.2.9 4.1.1.11 2.6.1.18 4.3.1.3 4.2.1.49 3HSO- 1.1.1.105 2.3.1.41 NADPH 1.1.1.22 2.3.1.4 5.5.1.4 3.2.1.26 3.2.1.48 2.6.1.16 1.1.1.14 2.7.7.34 4.2.1.47 2.4.1.68 2.4.1.69 2.4.1.9 5.3.1.8 2.4.1.11 O OPPU CH OH2 CH OH2 HO OH OH HO 2.4.1.21 4.2.1.52 1.2.1.18 4.2.1.18 O CH C CHOC N HN DP CH C O CHOC N HN RPPP OCH2 H C C H OHOH CH NHN C H CP H O OCH2 C C H OH H OH C H C C C NH2 C CH HC N RP(PP) N N N + P NH2H O OCH2 C C H OH H OH C H C C OC C CH HC N RP N N NHP H OCH2 C C H OHOH CO CH2 C CONH2 C CH HC N RP N N NHP + OOCCH N(CH )2 3 3 Betaine Betaine aldehyde 2.4.1.16 5.1.3.6 2.4.1.33 2.7.7.13 5.4.2.8 5.3.1.8 O OH CH OH2 HO O PHO 2.7.1.28 2.7.1.31 6.3.4.13 5.3.1.1 2.2.1.1 4.1.1.9 3.1.2.11 ß-OH-ß-Methyl- glutaryl-CoA 6.3.4.5 5.3.1.6 2.5.1.21 2.1.1.2 3.5.2.10 6.3.2.13 6.3.2.7-10 2.7.7.27 2.7.7.9 3.5.4.10 C C O C CH OC N RP N N H HN C C O C CH N N N HN RP H N2 C 2.7.4.6 1.17.4.1 2.7.4.6 2.6.1.13 Carbamoyl-P 2.3.1.9 Carnitine 2.6.1.4 2.6.1.44 CH C(OH)CH COSCoA3 2 CH COO2 1.2.3.5 1.1.1.34 2.3.1.16 4.1.3.5 2.3.1.16 4.1.3.4 Menaquinone 4.1.1.15 2.6.1.19 4.2.1.16 Carnosine CH CH NH2 2 2C NHN C HC H 4.1.1.22 4.3.1.3 Ubiquinone Plastoquinone D-Ribose-5-P NH CH CH(NH )COO2 3HO + O OH OH HO OPPU COO- O OH OH HO OPPU COO- OH H OH HOCH2 C C CO H CO COO- O CHOH CHOHAcNH HO OPC OCO - CH OH2 O CHOH CHOHAcNH HO OH COO CH OH2 O OHOHHOHO CH O2 P O OH ACNH HO OH CH O2 P O OOHHOHO P CH OH2 O OHOH HOHO CH OH2 O OHHO OH 3 CH O2 P O OHHO O NHCOCH3 P CH OH2CH OH2CH OH2 O OHHO OH NH2 CH O2 P O OH HO OH OPPU CH OH2 O O HO OH OH HO P CH OH2 CH OH2 O O HO OH OH O OHOH OH CH OH2 O OHHO OH OH CH2CH OP2 OH H H HOH C C C C OH OHH COO-HOCH2 H OH OHOH C C C CHO HH HOCH2 H OH OHH C C C CHO HOH HOCH2 OH H OHH C C C CHO HOH HOCH2 H OH HOH C C C CHO OHH HOCH2 OH H HOH C C C CHO OHH HOCH2 OH H OHOH C C C CHO HH HOCH2 H OH HOH C C C C OHH H OH COO-POCH2 OH H OH C C CO H POCH2 CH OH2 H OH H C C CO OH HOCH2 CH OH2 CH OH2POCH2 H OH OH C C CO H CH OH2POCH2 OH H H C C CO OH CH OH2 POCH2 H OH OH C C CO H HOCH2 CH OH2 OH H OH C C CO H HOCH2 CH OH2 OH H H C C CO OH HOCH2 CH OH2 H OH OHH C C C HOH HOCH2 CH OH2 OH H OHOH C C C HH HOCH2 CH OH2 H OH HOH C C C C OHH H OH CH OH2HOCH2 H OH OH C C CHO H POCH2 H OH HOH C C C CO OHH HOCH2 CH O2 P H OH OHOH C C C HH HOCH2 CH OH2 H OH OH C C C H CO H HO POCH2 CH OH2 P H OH OH C C C H CO H HO CH O2 POCH2 H OH OH C C H C CHO OH H POCH2POCH2 O OH NH2 OH CH O2 P CHOHCHOPOCH2 HOCH2COCH2OP O OH O OP P OH CH O2 P CHOHCOOPPOCH2 CHOHPOCH2 COO COO OH OHO OH COO CH (CH ) CH(OH)CH COS-CoA3 2 14 2CH (CH ) CH(OH)CH COS3 2 14 2 CH (CH ) COCH COS-CoA3 2 14 2 CH (CH ) COCH COS-CoA3 2 14 2 CH (CH ) COS-CoA3 2 n+2 CH (CH ) CH=CHCOS-CoA3 2 14 CH (CH )3 2 nCH=CHCOS-CoA CH (CH )3 2 5 2CH=CHCH COSACP CH (CH )3 2 6CH=CHCOSACP CH (CH )3 2 6COCH COSACP2CH (CH )3 2 6 2 2CH CH COSACP CH (CH )3 2 2 2 2CH CH COSACP CH CH CH COSACP3 2 2 CH (CH )3 2 6CH(OH)CH COSACP2 CH CH=CHCO.S-ACP3 CH (CH )3 2 2 2COCH COSACP CH3COCH COSACP2 CH (CH )3 2 n 2COCH COSACPCH (CH )3 2 n 2CH(OH)CH COSACP CH (CH )3 2 2 2CH(OH)CH COSACP ACYL-CoA (Mitochondria) CH (CH ) CH CH COSCoA3 2 2 2n CH (CH ) CH=CHCOSCoA3 2 n CH (CH CH(OH)CH COSCoA3 2n CH (CH ) CH CH COSCoA3 2 2 2 2 CH (CH ) CH=CHCOSCoA3 2 2 CH (CH ) COCH COSCoA3 2 2n CH COCH COSCoA3 2 CH (CH ) CH(OH)CH COSCoA3 2 2 2 CH CH(OH)CH COSCoA3 2CH CH=CHCOSCoA3CH CH CH COSCoA3 2 2 CH CH CH CH COSCoA3 2 2 2 Pentenoyl-CoA CH CH CH=CHCOSCoA3 2 CH CH CH(OH)CH COSCoA3 2 2 CH (CH ) COCH COSCoA3 2 2 2 CH CH COCH COSCoA3 2 2 OH OH HO OH O O- CH O-PO2 CH CHOHCH OH2 2 O CH2 CH2 R'-CO-OCH O-CO-R O-PO O- HOCH CH2 2 NH3 +POCH CH2 2NH3 + CPP-OCH CH2 2NH3 + O - CH O-CO-R2 CH O P2 OCH CH2 2NH3 + CH COCH CH N(CH )3 2 2 3 3 HOCH CH N(CH )2 2 3 3 + CH CH2 COO(NH )3 + OH OH CH CH2 COO-(NH )3 + CO NH2 CH CH(NH )COO2 3 + NH OC CO NH OC N H C H H N2 HC CH N N C RP H N2 CH C CHOC N N DP NH2 RPPP CH C CHOC N N NH2 C C C CH RP(P) HC N N N N NH2 H NCOO2 P (CH ) NH2 3 2H N(CH ) NH2 2 3 (CH ) NH2 4 (CH ) NH2 3 2H N(CH ) NH2 2 4 CH -SCH CH CHNH3 2 2 2 Adenosyl + + CH3 CH3 CHCH(NH )COO3 ++ C NHN C HC H CH CH(NH )CH OH2 3 2 + C NHN C HC H CH CH(NH )CH OP2 3 2 C NHN C H HC CH COCH OP2 2 + HSCH CH CH(NH )COO2 2 3 + + SCH CH CH(NH )COO2 2 3 CH CH(NH )COO2 3 RP C O C-COOOC N HN CH 2.4.1.23 CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2 NH3 + CH (CH ) CH(OH)CHCH OH3 2 14 2 NH3 + CH (CH ) COCHCH OH3 2 14 2 NH3 + GalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2 NH3 + 4.1.1.70 H NCONH2 2 OHCCH N(CH )2 3 3 + C-CH3 C O CHOC N DP HN DP CPP-OCH CH N(CH )2 2 3 3 + OCH CH N(CH )2 2 3 3 + 1.2.1.41 UDP-N-Ac-Muramate O O CH CH3 COO- NHAC HO OPPU CH OH2 4.1.3.20 O OH CH3 HO HO OPPG 2.7.7.24 2.4.1.22 2.7.7.12 5.1.3.2 5.3.1.4 Sedoheptulose-PP 3.1.1.28 4.2.1.24 N CH2 CH2 N N N CH3 CH3 CH CH COO CH CH CH2 H C3 H C3H C3 HC C C H H Fe CH2 CH2 COO- - CH3 CH3 CH2 CH2 CH2 H C3 H C3 N H N H N H N H CH CH H C2 C C H2 H2 - CH2 CH2 COO CH2 CH2 COO - H C2 H C2 CH 2 CH 2 OOC COO H N2 N H - - CH2 H C2 H C2 H C2 H2 H2 CH2 CH2 CH2 CH2 CH2 CH2 N H N H N H N H COO COO COO COO C C - - CH2 CH2 COO CH2 CH2 COO- - - - OOC- OOC - CH3 CH3 H C3 H C3 H C2 H2 H2 N H N H N H N H CH2 CH2 CH2 CH2 CH2 C C COO- CH2 CH2 COO CH2 CH2 COO- - COO- COO- CH C(OH)CH CH O3 2 2 PP CH COO2 OHCCOO HOCH COO2 NH2 H NCNHCH COO2 2 + NH2 H NCN(CH )CH COO2 3 2 + NH2 HNCN(CH )CH COO3 2P- + HN C NH CO N CH2 CH3 OOCCHCH COO2 H NCNHCH CH CH CH2 2 2 2 N (NH )3 + COO CHCOOHC CH2HOCH N OOCCH(OH)CH CH(NH )COO2 3 + CHCOO CH2HOCH H C2 N H NH CHCOO CH2CH2 CH2 OOCCH(OH)CH COCOO2 N CHCOO CH2CH2 CH CH COCOO3 OHCCOO + H NCONHCH CH CH CH2 2 2 2 (NH )3 COO H NOCCH CH CH2 2 2 COO(NH )3 + R-CO-COO + COOR-CH(NH )3 + COOH NOCCH CH2 2 (NH3 + OOC-CH-COSCoA CH3 P OOCCH CH2 COO(NH )3 + OOCCH CH CHO2 2 OHCCH CH2 COO(NH )3 + (CH ) NCH CH(OH)CH COO3 3 2 2 + OHCCH CH CH2 2 + COO(NH )3 POOCCH CH CH2 2 + COO(NH )3 OHCCH CH CH CH2 2 2 COO(NH )3 + NH CHCH CH COO2 2 COO CH CH CH CH CH2 2 2 2 COO(NH )3 + H N(CH )2 42 CH(NH )COO3CH(NH3 ++ (CH ) N(CH )3 3 2 3CH CH(NH )COO2 3 + + CH2 C H OOCC N HC CH-COO CH2 C H2 CH-COOOOCC N H C2 OOCCOCH CH CH CH-COO2 2 2CH CH2 2 2 OOCCH CH CONH2 2 OOCCHCH CH CH CH-COO2 2 2 OOCCH CH CONH2 2CH2 2 NH3 + OOCCH-CH CH CH CHCOO2 2 2 NH3 + NH3 + (CH ) CHC(OH)CH3 2 2 COOH COO (CH ) CHCH COCOO3 2 2 + (CH ) CHCH3 2 2 CH(NH )COO3 HOCH CHCOO2 CH3 CHCOCOO CH3 CH3CH COC(OH)CH3 3 COO + POCH CH CH(NH )COO2 2 3 + HOCH CH CH(NH )COO2 2 3 + CH CH CH(NH )COO2 2 3OOCCH CH2COO2 + CH SH2 OOCCH(NH )CH CH CONHCHCONHCH COO3 2 2 2 HOCH C(CH ) COCOO2 3 2 HOCH C(CH ) CH(OH)COO2 3 2 NHCH CH COO2 2HOCH C(CH ) CH(OH)CO3 2)2 3 2 NHCH CH COO2 2OCH C(CH ) CH(OH)CO2 3 2P CH CH3 2 CH3 CH + CH(NH )COO3 CH COC(OH)CH CH3 2 3 COO CHCOCOO CH CH3 2 CH3 NHCHCH SH2 COO NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P + CH SH2 OOCCH(NH )CH CH CONHCHCOO3 2 2 + Adenosyl SCH CH CH(NH )COO2 2 3 + SCH CH CH(NH )COO2 2 3 + HO SCH CH(NH )COO3 2 3 + + S-CH CH(NH )COO2 3 S-CH CH(NH )COO2 3 + HSCH CH(NH )COO2 3 1.1.1.23 H C NHN C HC CH CHCOO2 NHCOCH CH NH2 2 2 + H C NHN C HC CH CH(NH )COO2 3 CHCH CH COO2 2 NHN CH OC C CH CHCOO NHN CH CH CH COO3 N H OOC CH-COOOC NH2 CH2 H NCH CH COO2 2 2 H NCH2 2 CH3 CHCOO H NCONHCH CHCOO2 2 CH3 C C O CH RP HC N N N HN C CC O CH HCO N N N RP C CH N N H N2 H C C C O CH N N C C CH N N RP H N2 H N2 C O O O P~ ~P O O O O P O O CH2 N N N N O OHOH NH2 HC CH N N N N O O P O O O CH2 OH NH2 HC CH COO CO NH OC N H C H H N2 NH2 OOC-CH-CH COO2 HNCO C CH N N C RPRP H N2 OOC C CH N RP N C H N2 CH=CHCOO OH CH=CHCOO CH COCOO2 CH2 P COO OH O O O COO O CH COO2 O CH COO2-OOC OCH2 CH2 OHH C P HOCH HCOH OC COO COOHO OH OHO NH2 COO OCH NH CH COCOO2 NH CHO CO NH2 OH CH CH(NH )COO2 3 + N COO COO N + COO COO RP O OH OH HO OPPU COO O OH NHCOCH3 HO OPPU COO CH OH2 O O CCH2 NHAC HO OPPU COO CH OH2 O OHHO OH OH COO OOCCH N(CH )2 3 2 Dimethylglycine 1.1.99.1 1.2.1.8 COO HO HO COO O HO OH COO CH(O )PPOCH2 COO CH(OH)HOCH2 COOCOO CH(O )PHOCH2 COO CH =C(O )2 P COO CONH2 Ribose -O - P - O - P - O- Adenosine(P) + N O O O O + COO N Ribose - O - P - O - P - O -Adenosine O O O O II II OH O CH CH2 COO(NH )3 + Epinephrine (Adrenaline) Norepinephrine (Noradrenaline) Normetepinephrine (Normetadrenaline) HOCH CH N(CH )2 2 3 3 + Adenosyl + + SCH CH CH(NH )COO2 2 3 CH3 (CH ) N(CH )3 3 2 3CH CH(NH )COO2 3 + + OH OOCCH CH CH COSCoA2 2 2 OOCCH CH CH NH2 2 2 2 OOCCH CH CH COCOO2 2 2 OOCCH CH CH CH2 2 2 COOCOO(NH )3 ++ HO H HO H H HO H HO H Prostaglandin PGE2 OH HOCH2 C C CO C COO OHH OHH H - COO OR'-CO-OCH CH O-CO-R2 CH O POCMP2 O CH CH N(CH )2 2 3 + OHOCH CH OPO2 CH OH2 O- CH OPO2 O CH OCH=CHR2 CH CH N(CH )2 2 3 3 + O- CH OPO2 OR'-CO-OCH CH O-CO-R2 3.1.1.32 CH CH N(CH )2 2 3 3 + O- OHOCH CH OPO2 CH O-CO-R2 CH CH N(CH )2 2 3 3 + O- CH CH(NH )COO2 3 + + C NHN C HC H CH CH(NH )CHO2 3 HS 11-cis-Retinal Pi ADP NADP+ GDP- Mannuronate Mannose-6-P Dehydro- shikimate Shikimate RNA d-GDP d-CTP GUANOSINE-P (GMP) ß-Alanine P-Ribosyl-AMP P-Ribulosylformimino 5-aminoimidazole- carboxamide-R P Imidazole acetol-P HS HSO- PANTOTHENATE 3-Isopropyl- malate Succinic semialdehyde 2.4.1.17 Diacyl glycerol 2.3.1.6 1.14.12.1 1.4.4.2 CH CHO3 3.5.4.19 4.2.1.19 3.3.1.1 4.1.1.12 4.1.2.5 COO- 2OHCCH 2.1.4.1 2.4.99.7 5.1.3.12 1.1.1.132 4.2.1.46 2.7.1.7 2.4.1.29 2.4.1.21 2.4.1.13 2.4.1.1 etc. 5.4.2.2 2.7.1.6 2.7.7.10 3.1.1.18 4.1.1.34 2.7.1.47 2.7.1.16 3.1.3.9 ADP P-Glucono lactone 1.1.1.44 O O OHHO OH CH O2 P PHENYLALANINETYROSINE TRYPTOPHAN INOSINE-P (IMP) THYMIDINE-P HISTIDINE URIDINE- triphosphate (UTP) CYSTINE CYSTEINE ISOLEUCINE LEUCINE LYSINE ORNITHINE ARGININE HYDROXY PROLINE PHOSPHATIDYL SERINEPhosphatidyl inositol LECITHIN SPHINGOMYELIN STEROIDS Pregnenolone 2.7.6.1 2.4.2.14 6.3.4.7 5.3.1.9 3.1.3.11 1.2.1.13 2.7.2.3 H OH OH C C C H CO OH C H H OH POCH2 CH O2 P 5.4.2.1 ADP 4.2.1.11 Endoplasmic Reticulum 1.1.1.100 3.1.1.3 Phosphatidate 2.3.1.39 4.2.1.17 4.2.1.17 4.2.1.55 1.1.1.79 1.2.1.21 1.4.3.8 1.1.1.32 2.7.1.36 2.7.4.2 4.1.1.33 2.5.1.1 2.5.1.10 2.7.8.5 2.7.8.1 4.1.1.65 2.7.7.14 1.3.99.7 PO O CH (CH ) CH=CHCH(OH)CHCH O3 2 12 2 NHAcyl CH CH N(CH )2 2 3 3 + O- 3.5.1.23 1.13.11.21 2.5.1.32 1.1.1.105 2.4.2.19 1.2.1.32 METHIONINE 4.1.3.27 4.2.1.51 1.14.17.1 1.14.18.1 1.14.13.11 Glycinamide- ribosyl-P 4.2.1.22 3-Oxohexanoyl-CoA THREONINE 1.2.1.25 1.2.1.25 1.2.1.25 1.5.1.7 - 10 GLUTAMATE 2.3.1.38 ATP NADH SUCROSE ADENOSINE-P (AMP) Triacylglycerol FAT RNA CH3 CH2 OC-COOOH COO CH CH2 COO(NH )3 + GLYCOPROTEINS GANGLIOSIDES MUCINS 4.1.2.- 2.6.1.- GLUCOSE O-Acyl-carnitine O-Acyl-carnitine OH O- - R-CO-OCH R'-CO-OCH R'-CO-OCH O HCO-CO-R CH CH(OH)CH O-P-OCH2 2 2 CH O-CO-R’2 OR'-CO-OCH O- CH O-CO-R2 CH O-PO2 O- 2.7.8.11 H NCH CH CH CH2 2 2 2 COO(NH )3 + 2.3.1.20 3.1.3.4 2.7.1.107 NH2 + + H NCNHCH CH CH CH2 2 2 2 COO(NH )3 H OH HOH C C C CO OHH HOCH2 CH OH2 R-CH2COO CH O-CO-R2 CH O-CO-R"2 R’-CO-OCH OH O CH CHNH2 3 + OR'-CO-OCH O- CH O-CO-R2 CH O PO2 COO OOCCH CH CH2 2 COO(NH )3 + CH CH(OH)CH(NH )COO3 3 O OHHO OH OH CH OH2CH OH2 NH CH O-CO-R2 1.3.1.13 4.1.1.28 Malonic semi- aldehyde 2.7.2.4 2.1.3.3 3.5.1.2 6.3.1.2 6.3.5.5 Carbohydrates Biosynthesis Degradation Amino Acids Biosynthesis Degradation Lipids Biosynthesis Degradation Purines & Pyrimidines Biosynthesis Degradation Biosynthesis Degradation Vitamins Co-enzymes & Hormones Pentose Phosphate Pathway Photosynthesis Dark Reactions COMPARTMENTATION The "Backbone" of metabolism involves GLYCOLYSIS in the CYTOPLASM, the TCA CYCLE (mainly) in the Mitochondrial matrix and ATP FORMATION spanning the MITOCHONDRIAL INNER MEMBRANE An electron flow (an electric current) generated from NADH and UQH2 drives the translocation of protons from the matrix to the intermembrane space. The retrolocation of these protons through the F0 subunits of ATP synthase to the matrix then supplies the energy needed to form ATP from ADP and phosphate Electron Flow Proton Flow Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme Commission (EC) Reference Numbers of Enzymes LEGEND Human Metabolism is identified as far possible by black arrows Biosynthesis Degradation HEMOGLOBIN CHLOROPHYLL ATP TRANSLOC ATED PROTONS 2.7.1.1 ATP 2.7.1.2 Argentina SIGMA-ALDRICH DE ARGENTINA S.A. Free Tel: 0810 888 7446 Tel: (+54) 11 4556 1472 Fax: (+54) 11 4552 1698 Australia SIGMA-ALDRICH PTY LTD. Free Tel: 1800 800 097 Free Fax: 1800 800 096 Tel: (+61) 2 9841 0555 Fax: (+61) 2 9841 0500 Austria SIGMA-ALDRICH HANDELS GmbH Tel: (+43) 1 605 81 10 Fax: (+43) 1 605 81 20 Belgium SIGMA-ALDRICH NV/S.A. Free Tel: 0800 14747 Free Fax: 0800 14745 Tel: (+32) 3 899 13 01 Fax: (+32) 3 899 13 11 Brazil SIGMA-ALDRICH BRASIL LTDA. 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