MetabolicChart - Enzymes available from Sigma Enzymes...

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Unformatted text preview: Enzymes available from Sigma Enzymes available from Sigma Enzymes available from Sigma COO O O O O OXIDOREDUCTASES Alcohol dehydrogenase Homoserine dehydrogenase Glycerol-3-phosphate dehydrogenase D-Xylulose reductase l-Xylulose reductase l-Iditol dehydrogenase Glucuronate reductase Aldehyde reductase UDPglucose dehydrogenase Histidinol dehydrogenase Shikimate dehydrogenase Lactate dehydrogenase Glycerate dehydrogenase 3-Hydroxybutyrate dehydrogenase 3-Hydroxyisobutyrate dehydrogenase Mevaldate reductase Hydroxymethylglutaryl-CoA reductase (NADPH) 3-Hydroxyacyl-CoA dehydrogenase Malate dehydrogenase Malate dehydrogenase (decarboxylating) Isocitrate dehydrogenase (NAD+) Phosphogluconate dehydrogenase (decarboxylating) l-Gulonate dehydrogenase Glucose-6-phosphate dehydrogenase Ribitol dehydrogenase Glyoxylate reductase (NADP+) Hydroxypyruvate reductase Malate dehydrogenase (NADP+) 3-Isopropylmalate dehydrogenase Ketol-acid reductoisomerase Phosphoglycerate dehydrogenase 3-Oxoacyl-[acyl-carrier-protein] reductase 3-Dehydrosphinganine reductase Retinol dehydrogenase 3-Dehydro-L-gulonate 2-dehydrogenase 3-Hydroxybutyryl-CoA dehydrogenase UDP-N-acetylmuramate dehydrogenase 2-Dehydropantoate 2-reductase Xanthine dehydrogenase IMP-dehydrogenase l-Gulonolactone oxidase Xanthine oxidase Choline dehydrogenase Glycerol-3-phosphate dehydrogenase Aldehyde dehydrogenase (NAD+) Benzaldehyde dehydrogenase (NADP+) Betaine-aldehyde dehydrogenase Aspartate-semialdehyde dehydrogenase Glyceraldehyde-3-phosphate dehydrogenase Glyceraldehyde-3-phosphate dehydrogenase Succinate-semialdehyde dehydrogenase (NAD(P)+) Malonate semialdehyde dehydrogenase (acetylating) Glycolaldehyde dehydrogenase 2-Oxoaldehyde dehydrogenase (NAD+) Succinate-semialdehyde dehydrogenase 2-Oxoisovalerate dehydrogenase (acylating) Methylmalonate-semialdehyde dehydrogenase (acylating) l-Aminoadipate-semialdehyde dehydrogenase Aminomuconate-semialdehyde dehydrogenase Retinal dehydrogenase Glutamate-5-semialdehyde dehydrogenase Oxoglutarate dehydrogenase Glyoxylate oxidase Indole-3-acetaldehyde oxidase Pyruvate dehydrogenase (lipoamide) Oxoglutarate dehydrogenase (lipoamide) Pyruvate synthase 2-Oxobutyrate synthase Dihydrouracil dehydrogenase (NAD+) Dihydropyrimidine dehydrogenase (NADP+) Acyl-CoA dehydrogenase (NADP+) Enoyl-[acyl-carrier-protein] reductase (NADH) Enoyl-[acyl-carrier-protein] reductase (NADPH, B-specific) Prephenate dehydrogenase (NADP+) Orotate reductase (NADH) Dihydrodipicolinate reductase Phosphatidylcholine desaturase Coproporphyrinogen oxidase Protoporphyrinogen oxidase Succinate dehydrogenase (ubiquinone) Succinate dehydrogenase Butyryl-CoA dehydrogenase Acyl-CoA dehydrogenase Glutaryl-CoA dehydrogenase Isovaleryl-CoA dehydrogenase Alanine dehydrogenase Glutamate dehydrogenase Serine dehydrogenase Valine dehydrogenase (NADP+) Leucine dehydrogenase Glycine dehydrogenase Glutamate synthase (NADH) Tryptophan dehydrogenase d-Aspartate oxidase l-Amino-acid oxidase Amine oxidase (flavin-containing) Ethanolamine oxidase Glycine dehydrogenase (decarboxylating) Pyrroline-5-carboxylate reductase Dihydrofolate reductase Methylenetetrahydrofolate reductase (NADP+) Formyltetrahydrofolate dehydrogenase Saccharopine dehydrogenase (NAD+, l-lysine-forming) Saccharopine dehydrogenase (NADP+, l-lysine-forming) Saccharopine dehydrogenase (NAD+, l-glutamate-forming) Saccharopine dehydrogenase (NADP+, l-glutamate-forming) 1-Pyrroline-5-carboxylate dehydrogenase Sarcosine oxidase Sarcosine dehydrogenase Dimethylglycine dehydrogenase Proline dehydrogenase Cystine reductase (NADH) NADH dehydrogenase (ubiquinone) Nitrate reductase (NADH) Nitrate reductase [NAD(P)H] Nitrate reductase (NADPH) Nitrite reductase [NAD(P)H] GMP reductase Urate oxidase Ferredoxin—nitrate reductase Nitrate reductase Hypotaurine dehydrogenase Dihydrolipoamide dehydrogenase Sulfite dehydrogenase Sulfite oxidase Sulfite reductase (ferredoxin) Sulfite reductase Adenylsulphate reductase Cytochrome-c oxidase l-Ascorbate—cytochrome-b5 reductase Ubiquinol—cytochrome-c reductase l-Ascorbate oxidase Plastoquinol—plastocyanin reductase Catechol 1,2-dioxygenase Catechol 2,3-dioxygenase Homogentisate 1,2-dioxygenase 3-Hydroxyanthranilate 3,4-dioxygenase Tryptophan 2,3-dioxygenase Cysteine dioxygenase ß-Carotene 15,15´-dioxygenase 4-Hydroxyphenylpyruvate dioxygenase Arachidonate 5-lipoxygenase myo-lnositol oxygenase g-Butyrobetaine dioxygenase Procollagen-proline dioxygenase Trimethyllysine dioxygenase Anthranilate 1,2-dioxygenase (deaminating, decarboxylating) Imidazoleacetate 4-monooxygenase Kynurenine 3-monooxygenase trans-Cinnamate 4-monooxygenase Benzoate 4-monooxygenase Nitric oxide synthase Phenylalanine 4-monooxygenase Tyrosine 3-monooxygenase Tryptophan 5-monooxygenase Dopamine ß-monooxygenase Monophenol monooxygenase 1 14.99.1 Prostaglandin synthase 1 14.99.5 Stearoyl-CoA desaturase Squalene monooxygenase Linoleoyl-CoA desaturase Ribonucleoside-diphosphate reductase Nitrogenase TRANSFERASES Nicotinamide N-methyltransferase Guanidinoacetate N-methyltransferase Thetin—homocysteine S-methyltransferase Acetylserotonin N-methyltransferase Betaine—homocysteine S-methyltransferase Catechol O-methyl transferase Homocysteine S-methyltransferase 5-Methyltetrahydrofolate—homocysteine S-methyl transferase 5-Methyltetrahydropteroyltriglutamate — homocysteine S-methyltransferase Phosphatidylethanolamine N-methyltransferase Glycine N-methyltransferase Phenylethanolamine N-methyltransferase Thymidylate synthase Phosphatidyl-N-methylethanolamine N-methyltransferase Glycine hydroxymethyltransferase Phosphoribosylglycinamide formyltransferase Phosphoribosylaminoimidazole carboxamide formyltransferase Glutamate formiminotransferase Aminomethyl transferase Methylmalonyl-CoA carboxyltransferase Aspartate carbamoyltransferase Ornithine carbamoyltransferase Glycine amidinotransferase Transketolase Transaldolase Amino-acid N-acetyltransferase Glucosamine-phosphate N-acetyltransferase Arylamine N-acetyltransferase Choline O-acetyltransferase Carnitine O-acetyltransferase Phosphate acetyltransferase Acetyl-CoA C-acetyltransferase Dihydrolipoamide S-acetyltransferase Glycerol-3-phosphate O-acyltransferase Acetyl-CoA C-acyltransferase Diacylglycerol O-acyltransferase Lysolecithin acyltransferase Sphingosine N-acyltransferase Serine O-acetyltransferase 5-Aminolevulinate synthase [Acyl-carrier-protein] S-acetyltransferase [Acyl-carrier-protein] S-malonytransferase 3-Oxoacyl-[acyl-carrier-protein] synthase Homoserine O-succinyltransferase Serine C-palmitoyltransferase 1-Acylglycerol-3-phosphate O-acyltransferase Retinol O-fatty-acyltransferase Phosphorylase Inulosucrase 2 4.1.11 Glycogen (starch) synthase Sucrose synthase Chitin synthase Glucuranosyltransferase Starch synthase Lactose synthase Sphingosine ß-galactosyltransferase Cellulose synthase (GDP-forming) Glucomannan 4-ß-mannosyltransferase Alginate synthase Acylsphingosine galactosyltransferase Ganglioside galactosyltransferase Glycoprotein 6-a-l-fucosyltransferase Galactoside 2-a-l-fucosyltransferase Purine-nucleoside phosphorylase Pyrimidine-nucleoside phosphorylase Thymidine phosphorylase Hypoxanthine phosphoribosyltransferase Uracil phosphoribosyltransferase Orotate phosphoribosyltransferase Nicotinate phosphoribosyltransferase Amidophosphoribosyltransferase Guanosine phosphorylase ATP phosphoribosyltransferase Anthranilate phosphoribosyltransferase Nicotinate-nucleotide pyrophosphorylase (carboxylating) Sialyltransferases Sialyltransferase Dimethylallyltranstransferase Methionine adenosyltransferase Geranyltranstransferase Spermidine synthase 3-Phosphoshikimate 1-carboxyvinyl-transferase Farnesyltransferase Spermine synthase Farnesyltranstransferase Geranylgeranyl-diphosphate geranylgeranyl transferase 2.6.1.Transaminases Aspartate transaminase 2.6 1.2 Alanine transaminase Glycine transaminase 2.6 1.5 Tyrosine transaminase 2.6 1.6 Leucine transaminase Histidinol-phosphate transaminase Ornithine—oxo-acid transaminase Glutamine—fructose-6-phosphate transaminase Succinyldiaminopimelate transaminase ß-Alanine—pyruvate transaminase 4-Aminobutyrate transaminase l-3-Aminoisobutyrate transaminase 4-Hydroxyglutamate transaminase Tryptophan transaminase Valine—3-methyl-2-oxovalerate transaminase l-Lysine 6-transaminase 2-Aminoadipate transaminase Branched-chain-amino-acid transaminase Alanine-glyoxylate transaminase Serine—pyruvate transaminase Phosphoserine transaminase Valine—pyruvate transaminase Hexokinase Glucokinase Ketohexokinase Fructokinase Galactokinase Mannokinase 6-Phosphofructokinase P O L Y S A C C H A R I D E S GLYCOPROTEINS GANGLIOSIDES MUCINS AcNH CHOH CHOH HYALURONIC ACID PEPTIDOCHITIN GLYCAN CH OH 2 DERMATAN CHONDROITIN O COO - BLOOD GROUP ALGINATES O-ANTIGENS STARCH SUBSTANCES PECTIN INULIN CELLULOSE O CH3 HO HO OPPG OH HO CH3 O OPPT OH OH CH3 GLYCOGEN HO CH2OH O O OH OH OH OH OH CH2OH O NH CONH 2 CH2COO OH N + Ribose -O - P - O - P - O- Adenosine(P) + N + O O O + N COO Ribose - O - P - O - P - O -Adenosine O NICOTINATE 2.4.2 .11 N COO COO + COO N RP O O Indoleacetate (Auxin) CH2CHO Indoxyl HO NH NH NAD(P) NH HO NH CH 2CH2NH 2 Desamino-NAD HO COO OPC CH2OH HO HO O CH3CH COO- Nicotinatenucleotide CH3O NH Ribose- P CH 2CH2NHCOCH 3 Quinolinatenucleotide N OPPU NHAC HO OH OPPU OH HO etc. UDP-N-Ac-Muramate CH2OH O COO HO UDPIduronate COO HO OH O CMP-N-Acetyl neuraminate AcNH O CHOH CHOH CH2OH COO OH GDP-Fucose CH2OH O GDPMannuronate TDP-Rhamnose O OPPT OH CH2OH O OH LACTOSE + CH2CH(NH3)COO CH2CH2NHCOCH 3 COO COO O CH2OH O HO OH HO OH OH OH Indoleacetaldehyde CH 2COCOO NH NH Indole 5-Hydroxytryptophan + CO CH2CH(NH 3)COO CHO 5-Hydroxytryptamine N-Acetyl-serotonin (SEROTONIN) + COCH2CH(NH 3)COO OH NH2 COO OH NH2 NH N-Acetyl-5-O-methyl-serotonin (MELATONIN) COO OCH NH2 COO Quinolinate OH OH OPPU NHCOCH 3 HO OH HO OPPG CH2OH O GDP-Mannose OPPU OH CH2OH O TDP-4-Oxo6-deoxyglucose ADPGlucose CH2OH O OH HO OH HO GALACTOSE OPPU HO CH2OH O OH OP OH + CO CH2CH(NH 3)COO NH2 HO N-Ac-Neuraminate CH2OP O (Sialate) HO O CH2 C COO OPPU NHAC UDP-N-AcGalactosamine COO O Indolepyruvate Formylkynurenine + CH2CH(NH 3)COO NH NH Kynurenine 3-Hydroxy kynurenine C-CH(OH)CH(OH)CH 2OP CH UDPGalacturonate OPPU MANNOSE CH 2OP O GDP-Glucose 2 UDP-Glucose Galactose-P CH 2OH O HO OH HO HO OH CH2CH 2NH2 UDP-N-AcGlucosamine pyruvate N-Ac-Mannosamine-6-P ACNH HO OH OH CH2OH O CH2OH O HO OH HO O P HO OH OH Mannose-1-P TDP-Glucose CH 2OH O OPPU OH Tryptamine COO OC P OCH 2 CH2 HOCH HCOH C NH TRYPTOPHAN HO COO OH OH N Indole-3-glycerol-P COO HO OH H 1-(o-Carboxy phenylamino) 1-deoxyribulose-5-P COO COO HOC-CH(OH)CH(OH)CH 2OP CH N 3-Hydroxy 2-Amino-3-carboxy 2-Aminomuconateanthranilate muconate semialdehyde 6-semialdehyde COO HH Catechol NH C C CH CH2OP OH OH COO NH2 OCH NH2 COO A R O M A T I C A M I N O A C I D S OOC OOC CH 2COCOO NH 2 H N-(5-P-Ribosyl) anthranilate COO CH2 O Anthranilate OOC UDP-Glucuronate CH2OH O CH2OP O OP NHCOCH 3 HO OH OH COO OH OH COO 2-Amino muconate OPPU HO OH HO OH CH2 OH H E X O S E S ACNH HO OH OH HO OH NHAC HO OH Mannose-6-P CH 2OP O HO OH OH NH2 OP UDP-Galactose CH2OH O N-Ac-Mannosamine UDP-N-Ac-Glucosamine COO O OH N-Ac-Glucosamine-1-P OH OH OH OH OP HO OH OH N-Ac-Glucosamine-6-P H H C OH C CO CH2OH NHCOCH 3 Glucose-1-P 3-Deoxy-D-arabinoheptulosonate-7-P O -OOC O CH2COO H OH O O Dehydroquinate O Dehydroshikimate CH2COO Shikimate OH PO OH CH2COCOO Shikimate-3-P PEP OH OH PO Shikimate-5 enolpyruvate 3-P + OH O-C-COO Chorismate + OH OC-COO Prephenate CH2COCOO CH2CH(NH3) COO CH2CH(NH3) COO 2.3.1 .4 OH H HOCH 2 C H C OH OH C C H HOCH 2 C Glucosamine-6-P HO OH OH OH COO - OH OH H HO OH OH OH HO OH Gulonate OH H C H C OH H OH OH C H O C H CO Glucuronate OH H C H C HOCH 2 OH C H O CO CO Inositol HOCH 2 C H OH H C Inositol-P C CO OH Fructose H H C OH H C C CH2OH OH SUCROSE GLUCOSE Fumaryl Maleyl Homogentisate acetoacetate acetoacetate CHOHCH 2NHCH 3 OH CHOHCH 2NH2 OH COO O CH2COO 2.7 1.47 OH Hydroxyphenyl pyruvate OH OH + OH TYROSINE PHENYLALANINE 4.1 .1.2 5 CH2CH2NH2 4.3.1 .5 Phenylpyruvate CH2CH2NH2 CH2CH(NH3) COOOH CH=CHCOO HOCH 2 OH OH C O HOCH 2 C CH2OP O 1 ATP Epinephrine (Adrenaline) OH Norepinephrine (Noradrenaline) 6 .1. 2.1 OH Dopamine α-Tocopherol (Vitamin E) OH O Dopa H2 C CH-COO + NH3 OH Ubiquinone O O + CH2CH(NH3) COO Gulonolactone 2-Oxogulonolactone OH H C OH OH HOCH 2 C H CO C COOH OH H HOCH 2 C H C OH CO CO COO - ASCORBATE OH H HOCH2 C H C CO O CO OH OH H O Tyramine OH Cinnamate Menaquinone CH=CHCOO Sorbitol H POCH2 C H C OH H C C COO - 2.7 CO .1. 4 HO OH OH ADP CHOHCH 2NH2 OCH 3 OH HN P E N T O S E S 3-Dehydrogulonate OH H HOCH 2 C H C OH C CHO H 2, 3-Dioxogulonate H C OH C CHO H HOCH 2 C H C Dehydroascorbate CO CH 2OH H H C 3 .17 .1.1 P-Glucono lactone Glucose-6-P CH2 OP O OH OH I O I CH(OH)COO OCH 3 HO OH Normetepinephrine (Normetadrenaline) CHOHCH 2OH OCH 3 OH Coumarate NADP + OH HOCH 2 C OH H L-Xylose OH H HOCH 2 C H C H C OH OH CH2OH D-Arabinose D-Ribulose OH H HOCH 2 C H C OH CO CH 2OH POCH2 OH H C H C OH CO OH OH H OH OH OH C CO HOCH 2 C CH2OP OH OH H OH 6-P-Gluconate NADPH 4-OH-3-MethoxyD-mandelate CH2OP O NHCOCH 2NH2 H 2C OC NH CHO NH RP 4 .3. 1.4 Dopaquinone Plastoquinone O O O NH OH I OH I 4-OH-3-Methoxyphenylglycol NH H 2C HN C CHO NH RP MELANIN THYROXINE OOC-CH-CH 2COO HNCO C N LIGNIN Tannins O C Plant Pigments NADP + CH2OH HOCH 2 Fructose-1-P H H H OH OH H H H C CO CH2OH H POCH 2 C H H H C HO C CO CH2OH POCH2 C L-Arabitol HOCH 2 C H C H L-Xylulose H CHO HOCH 2 C OH H C C OH CH 2OH NADPH L-Xylulose-5-P H HOCH 2 C OH H C C OH OH H OH OH C C C CH2OH POCH2 Fructose-6-P ATP C CHO OH OH H OH OH H C OH OH OH OH CHO Ribitol H H C C Glycinamideribosyl-P OH OH HC H 2N C N CH N OOC N C C CH N RP Formyl Formyl glycinamide-R P glycinamidine-R P H2NCONH 2 5-Amino imidazole-R P OC C N H NH H NH CO HN OC RP 5-Amino-4-imidazole H2 N H 2N C CH H 2N C N CH RP O CC NH C N carboxylate-R P HN O C N 5-Amino-4-imidazole (N-succinylcarboxamide)-R P HN HC O C N N C C CH NH RP 5-Aminoimidazole carboxamide-R P H 2N CN OH OH L-Arabinose OH H HOCH 2 C H C H C OH OH 5.3 .1. 4 HOCH 2 OH H OH OH C H C H Xylitol D-Xylose POCH2 C H H HOCH 2 C C H OH C CO CH2OH CO CH OH 2 H C CHO D-Ribulose-5-P H POCH 2 C OH C CO CH 2OH HOCH 2 C Erythrose-4-P POCH 2 OH OH ADP HO C CO CH2OP CH2OP O Urea H 2N OC COO C NH H NH2 CO NH H2 N OC O H2 N HCO N CH N RP C A T E C H O L A M I N E S Ribokinase Ribulokinase Xylulokinase Phosphoribulokinase Dephospho-CoA kinase Adenylylsulfate kinase Triokinase Glycerol kinase Glycerate kinase Choline kinase Pantothenate kinase Pantetheine kinase Mevalonate kinase Homoserine kinase Pyruvate kinase D-Ribulokinase l-Xylulokinase N-Acylmannosamine kinase Shikimate kinase Pyrophosphate—serine phosphotransferase Ethanolamine kinase Diacylglycerol kinase Phosphoglycerate kinase Aspartate kinase Formate kinase Glutamate 5-kinase Creatine kinase Phosphomevalonate kinase Adenylate kinase Nucleoside-phosphate kinase Nucleoside-diphosphate kinase Guanylate kinase dtmp kinase Cytidylate kinase Ribose-phosphate pyrophosphokinase Pantetheine-phosphate adenylyltransferase Sulfate adenylyl transferase RNA nucleotidyltransferase (DNA-directed) DNA nucleotidyltransferase (DNA-directed) UTP—glucose-1-phosphate uridylyltransferase UTP—hexose-1-phosphate uridylyltransferase UDP glucose—hexose-1-phosphate uridylyltransferase Mannose-1-phosphate guanylyltransferase Ethanolamine-phosphate cytidylyltransferase Choline-phosphate cytidylyltransferase Nicotinate-nucleotide adenylyltransferase UDP-N-acetylglucosamine pyrophosphorylase Glucose-1-phosphate thymidylyltransferase Glucose-1-phosphate adenylyltransferase Glucose-1-phosphate guanylyltransferase Phosphatidate cytidylyltransferase N-Acylneuraminate cytidylyltransferase Ethanolamine phosphotransferase Diacylglycerol cholinephosphotransferase Ceramide cholinephosphotransferase CDPdiacylglycerol—glycerol-3phosphate 3-phosphatidyltransferase CDPdiacylglycerol—serine O-phosphatidyltransferase CDPdiacylglycerol—inositol 3-phosphatidyltransferase 3-Oxoacid CoA-transferase 3-Oxoadipate CoA-transferase 19 1. 4. 1. C N H NH C C CO NH H C H C CHO CO CH2OH D-Ribose OH OH OH L-Lyxose L-Ribulose L-Ribulose-5-P OH H OH OH H 4.1.2.- 1.1.1 .9 D-Xylulose D-Xylulose-5-P 2.7 .1. 15 OH H Fructose1:6-bis-P NH2 4 .1. 2.6 .10 1 20 .4. 1 1. 1. GLYCINE O CH2(NH3)COO + Allantoate N NH2 Allantoin O O O N NH2 URATE N CH N Hypoxanthine Xanthine C CH C OC NH NH Inosine 3.1.3 .5 Formylamidoimidazolecarboxamide-R P HN O C N N C C CH N RP HC N CH O P O O HC H POCH 2 C H C H C CHO POCH2 H C H C H OH C C CO CH2OP P-Ribosyl amine OH OH Glyoxylate Sarcosine 2. OOCCH 2NHCH3 N CH2 O N N -O P~O P~O P O CH 2O O O O HC NH2 N C N C CH C HC N RP(P) N OOC-CH-CH 2COO Fumarate (AMP) OH OOCCH 2N(CH3)2 Cyclic AMP ATP d-ADP OH OH ADP ADENOSINE-P Adenine NH N C C N CH C HC NH RP N Aspartate INOSINE-P (IMP) HN O C N N C C CH N RP Adenylosuccinate 3.5.4 .3 OC P H O T O S Y N T H E S I S Chlorophyll Pheophytin PHOTOSYSTEM II 2H + Chloroplast Stroma PHOTOSYSTEM I D-Ribose-5-P ADP+P i OH OH OH Dimethylglycine OOCCH2N(CH3)3 + Sedoheptulose-PP POCH 2CHOHCHO OH OH OH H 2.7.7 .7 DNA RNA O C d-GTP d-CTP GTP TTP 2.7. 2.7 .7 . 6 d-GDP XANTHOSINE-P (XMP) 2.4.2 .1 HN H2 N C O C N N C C CH N RP H P U R I N E S Ferredoxin 2e* ATP Betaine + d-ATP 2e* 3H+ PQ Cyt. b 2e* 2H + Mn e- PQH2 Thylakoid Membrane 2H+ Dihydroxyacetone-P (Glycerone-P) HOCH2CO CH2OP 5.3 .1.1 5.3.1 3-P-Glyceraldehyde .1 Pi Pi NAD+ OHCCH 2N(CH3)3 Betaine aldehyde FOLIC ACID C1 POOL ATP 0 2.7 .7 .7 1.1 7.4 .1 Guanine GDP 2.7 .7.6 O C 4.6 1.17.4 .1 O C GUANOSINE-P (GMP) NH2 C CH CH OC N DP N f PC P680 2H2O 3H 2H+ Tr P700 ns H ans located proto H H H + + + + PC + NADP + HOCH2CH2N (CH3) 3 CH3 H2NCH 2 CHCOO CH3 H2NCONHCH 2CHCOO HN OC H + + + O2 Thylakoid Lumen Thylakoid Membrane H + H + H+ H H+ H + NADPH+H + H H C CO CH 2OP Glyceraldehyde CH2OP O HOCH 2CH(OH)CHO CHOLINE NADH HOCH2CH(NH3)COO + SERINE 3-Aminoisobutyrate 2. 1. 1. 13 ß-Ureido isobutyrate Dihydro thymine CH-CH3 CH 2 NH HN OC C CH 3 CH NH O C TDP O C O 2.7 .4.9 HN OC Thymine HN OC C-CH3 CH N DP C THYMIDINE-P 2.4.2 .4 O C CH HN CH OC N DP d-UMP d-CMP d-CDP HN H2NCONHCH 2CH 2COO Mg ++ P OCH 2 C OH OH Chloroplast Stroma Ribulose-1:5-bis-P Fixation CO2 COO HO HO COO OH OH OP O P 1:3-bis-P-Glycerate ADP POCH 2CHOHCOO P H2NCH 2CH2COO HOCH2COCOO ß-Alanine P-Ribosyl-PP Hydroxypyruvate + P OCH2CH(NH3)COO -OOC NH2 CH2 OC CH-COO N Carbamoyl ß-alanine HN OC O C Dihydrouracil HN OC O C CH2 CH2 OC NH Uracil O C N NH CH CH CH2 O2 COO ATP OH COO HO O OH Phosphoserine Carbamoyl aspartate H H C H C H C H URIDINEDihydro Orotate Orotidine-P Uridine-P UDP (UMP) triphosphate orotate (UTP) H P OCH 2 C H C H C H C NH 2 N OC C NH CH C HC N N H P OCH 2 C H C CO CH2 N NH C CH C HC N N RP CONH 2 CH-COO NH CH C-COO NH HN OC CH C-COO RP CH HN OC N CH RP HN OC CH CH N RPPP O C Cytosine N OC NH 2 C CH N CH OC NH NH 2 CDP C N CH CH RPPP CYTIDINEtriphosphate (CTP) H H C C C H CH N P Y R I M I D I N E S Linoleate COO COSCoA γ-Linolenate Arachidonate CO-S-ACP L I P I D B I O S Y N T H E S I S 5. 1.1 3.99 4.9 .3 9 .1 O Leukotriene B4 COO 3-P-Glycerate POCH2CHOH COO P-Hydroxypyruvate HC N P OCH2COCOO P OCH2 C P-Ribosyl-ATP C CH 2CHCOO NH C H OH OH O NH2 N +C C N CH C HC N N RP(PP) HYDROLASES Triacylglycerol lipase Phospholipase A2 Lysophospholipase Acetylcholinesterase Gluconolactonase Retinyl-palmitate esterase Acylcarnitine hydrolase 6-Phosphogluconolactonase Phospholipase A1 Acetyl-CoA hydrolase Succinyl-CoA hydrolase 3-Hydroxyisobutyryl-CoA hydrolase Acetoacetyl-CoA hydrolase Acyl-CoA hydrolase Acid phosphatase Phosphoserine phosphatase Phosphatidate phosphatase 5´-Nucleotidase Glucose-6-phosphatase Fructose-bisphosphatase Histidinol-phosphatase myo-Inositol-1(or 4)-monophosphatase Phosphatidylglycerophosphatase N-Acylneuraminate-9-phosphatase Nucleotidase Glycerophosphocholine phosphodiesterase Phospholipase C Phospholipase D 1-Phosphatidylinositol phosphodieterase Sphingomyelin phosphodiesterase ß-Glucosidase ß-Galactosidase ß-Fructofuranosidase Glucosylceramidase Galactosylceramidase Sucrose a-glucosidase Inosine nucleosidase Adenosylhomocysteinase Asparaginase Glutaminase ß-Ureidopropionase Arylformamidase Succinyl-diaminopimelate desuccinylase Pantothenase Ceramidase Dihydropyrimidinase Dihydroorotase Allantoinase Imidazolonepropionase Creatininase Arginase Allantoicase Arginine deiminase Cytosine deaminase Guanine deaminase AMP deaminase IMP cyclohydrolase dCMP deaminase Phosphoribosyl-AMP cyclohydrolase Adenosinetriphosphatase Nucleoside-triphosphatase Phosphoribosyl-ATP pyrophosphatase H+-transporting ATP synthase Fumarylacetoacetase Kynureninase Phosphoamidase LYSASES 4 1.1.21 4.2 1.46 P-Ribosyl-AMP C NH CH + CH2CH(NH 3)COO OH OH O OH OH P OCH 2 C Oleoyl-CoA Stearoyl-CoA CH3(CH2)14COS-ACP COSCoA Palmitoleoyl-ACP Dehydrostearoyl-CoA Palmitoyl-CoA 2, CH3(CH2)n CH=CHCOS-CoA CH 3(CH2)14COSCoA CH3(CH2)14CH=CHCOS-CoA Prostaglandin PGE 2 CH3(CH2)14CH(OH)CH 2COS-CoA COS HO OH Thromboxane B2 CH3(CH2)14COCH 2COS-CoA OH-Stearoyl-CoA Oxostearoyl-CoA Mitochondrial 2, 3-Diphosphoglycerate POCH2CH(O P) COO HOCH2CH(OH) COO Glycerate Carnosine NHCOCH 2CH2NH2 HC N HC N C NH CH P-Ribulosylformimino P-Ribosylformimino 5-aminoimidazole- 5-aminoimidazolecarboxamide-R P carboxamide-R P + + + CH2CH(NH 3)CHO HC N C CH 2CH(NH 3)CH2OH HC N C RP OH OH HN Imidazole glycerol-P HC N C H C NH CH2COCH 2OP CH2CH(NH 3)CH2OP CH3(CH2)14COCH 2COS-CoA Endoplasmic Reticulum ACETATE CH 3COO HISTIDINE Histidinal OOC HN Histidinol OC N NH CH Histidinol-P NH CH CH N C Palmitoyl-ACP ACYL-ACP CH3(CH2)6CH2CH 2COSACP Chain elongation CH 3(CH2)n CH(OH)CH 2COSACP 3-Enoyl-ACP 3-OH-Acyl-ACP 3-Oxoacyl-ACP CH 3(CH2)n COCH 2COSACP 2-P-Glycerate HOCH2CH(O P)COO Imidazole acetol-P CH CHCOO HC C C H NH CH2CH2NH2 N CHCH 2CH2COO NH CH CHCH 2CH2COO NH CH HISTAMINE Decanoyl-ACP Hexanoyl-ACP Butanoyl-ACP 1.3.1 .9 3, 4-Decenoyl-ACP 2, 3-Decenoyl-ACP 2, 3-Hexenoyl-ACP Crotonoyl-ACP CH3CH=CHCO-S-ACP CH3(CH2)2CH=CHCO-S-ACP CH3(CH2)6CH=CHCOSACP CH3(CH2)5CH=CHCH 2COSACP ETHANOL CH3CH 2OH CH (CH ) CH(OH)CH COSACP 3 26 2 0 4 0 .2.1.6 2.3 Formimino glutamate Imidazolone propionate NH CH Urocanate 2SO 4 3-OH-Decanoyl-ACP CH3(CH2)2CH(OH)CH 2COSACP 3-Oxo-Decanoyl-ACP CH 3(CH2)6COCH 2COSACP .1.3 0 + CH2CO-OCH2CH(NH 3)COO Acetylserine + S-CH 2CH(NH 3)COO + S-CH 2CH(NH 3)COO HS CH 3(CH2)2CH 2CH2COSACP CH3CH=CHCO.S-ACP 3-OH-Hexanoyl-ACP 3-OH-Butanoyl-ACP CH2OH HOCH CH2 OH HOCH CH2O P 3-Oxo-Hexanoyl-ACP Acetoacetyl-ACP CH3COCH 2COSACP CH3(CH2)2COCH 2COSACP P-enolpyruvate ADP Malonyl-ACP 2 .1. 3.7 HOOCCH 2CO-S-ACP CH2=C(OP ) COO HSO3 Acetaldehyde HS 4.1 1 .1. CH3CHO Phosphoadenylylsulphate (PAPS) Adenylylsulphate (APS) 4.2 .99 + .8 HSCH 2CH(NH 3)COO CYSTINE CYSTEINE + CH2CH(NH 3)COO + SCH 2CH2CH(NH 3)COO Cystathionine + HSCH 2CH2CH(NH 3)COO Homocysteine + CH 3 - SCH 2CH2CH(NH 3)COO METHIONINE + CH 3 - SCH 2CH 2CH(NH 3)COO + CH3CH2CH2COSACP CH3CH(OH)CH 2COS-ACP + HO 2SCH 2CH(NH 3 )COO Adenosyl R-CH2COO CH2OH CH3(CH2)n +2COS-CoA FATTY ACID ATP HSO3 Cysteine + HO3SCH 2CH(NH 3)COO Glutamate 4.1 .1. 29 Cysteate 6.3.2 .2 HO3SCH 2CH2NH2 S-Adenosyl homocysteine CH2SH + OOCCH(NH 3)CH2CH2CONHCHCOO + SCH 2CH2CH(NH 3)COO Adenosyl ACYL-CoA (Cytosol) Glycerol CH2O-CO-R CH2O-CO-R" 3-P-Glycerol CH2O-CO-R KETONE BODIES Acetone 3-OH-Butyrate CH3COCH 3 CH3CH(OH)CH 2COO HO2SCH 2COCOO L I P I D D E G R A D A T I O N Carnitine O-Acyl-carnitine O-Acyl-carnitine CH3(CH2)n CH2CH2COSCoA R’-CO-OCH CH2O-CO-R R’-CO-OCH CH2OH Malonyl-Co-A CH 3CO-S-ACP HOOCCH 2CO-SCoA PYRUVATE CH3CO COO 4.1.3 .18 + CH3CH(NH3)COO 3-Sulphinyl pyruvate sulphinate R’-CO-OCH CH2O P Triacylglycerol FAT Diacyl glycerol Phosphatidate Acetoacetate CH3(CH2)n COCH 2COSCoA CH3COCH 2COO Acetyl-ACP ALANINE Hypotaurine HO2SCH 2CH2NH2 Taurine γ-Glutamylcysteine 6.3.2 .3 Glycine + CH3CH(OH)CH(NH 3)COO + OOCCH2CH2COOCH2CH2CH(NH 3)COO CH3CH(OH)COO Succinylhomoserine CH3 CH3 CH2SH + OOCCH(NH 3)CH2CH2CONHCHCONHCH 2COO 1.1 .1.2 7 ACYL-CoA (Mitochondria) CH3(CH2)n CH=CHCOSCoA 2, 3-Enoyl-CoA CH3(CH n CH(OH)CH 2COSCoA 3-OH-Acyl-CoA 3-Oxoacyl-CoA CH 3 COSCoA ATP GTP LACTATE THREONINE 4.1.3 .18 + POCH 2CH2CH(NH 3)COO O-Phospho- homoserine COO + HOCH 2CH2CH(NH 3)COO Bile Acids HCHO CH3 + CHCH(NH 3)COO CH3 Glutathione HOCH 2 C(CH 3)2COCOO Oxopantoate 4.2 .1. 5 2 CH3(CH2)2CH2CH2COSCoA Hexanoyl-CoA CH3CH2CH2COSCoA 2, 3-Hexenoyl-CoA Crotonoyl-CoA Pentenoyl-CoA CH 2O-CO-R CH3CH2CH=CHCOSCoA CH3CH=CHCOSCoA CH3(CH2)2CH=CHCOSCoA 3-OH-Hexanoyl-CoA 3-OH-Butanoyl-CoA CH3CH2CH(OH)CH 2COSCoA CH3CH(OH)CH 2COSCoA CH3(CH2)2CH(OH)CH 2COSCoA 3-Oxohexanoyl-CoA Acetoacetyl-CoA 3-Oxopentanoyl-CoA OHCCOO CH3CH2COCH 2COSCoA CH3COCH 2COSCoA CH3(CH2)2COCH 2COSCoA ACETYL-CoA Malonic semialdehyde OHCCH 2COO CH3 CH3CH2COCOO 2-Acetolactate Oxobutyrate 4.1 .3.1 8 CH3 HOCH 2CHCOO CH3COC(OH)CH 3 2-3-Dihydroxy isovalerate CH3 C (OH)CH(OH)COO CH3 CHCOCOO 2-Oxo- VALINE isovalerate CH3 CH3 Pantoate ß-Alanine HOCH 2 C(CH 3)2CH(OH)COO Butanoyl-CoA Odd C Fatty acids Pentanoyl-CoA CH2O-CO-R R'-CO-OCH O CH2O-PO O OH OH CH 3CH2CH 2CH2COSCoA 3-OH-Pentanoyl-CoA CH 2O-CO-R R'-CO-OCH O O CH2O POCMP 4 OOCCOCH 2COO Methylmalonyl semialdehyde 2.3.1 .16 CH3 OHCCHCOO .31 1.1.1 3-Hydroxyisobutyrate COO CH3COC(OH)CH 2CH3 3-HydroxyIsobutyryl-CoA CH3 HOCH 2CHCOS-CoA- Methyl acrylyl-CoA CH3 CHCOCOO CH2 = CCOSCoA Isobutyryl-CoA CH 3 + CHCH(NH 3)COO CH3CHCO-SCoA HOCH 2 C(CH3)2CH(OH)CO NHCH 2CH2COO PANTOTHENATE R'-CO-OCH HO OH OH - Phosphatidyl inositol PHOSPHATIDYL SERINE O COO + CH 2O PO CH 2CHNH 3 O Glyoxylate HOCH 2COO CH2COO CH3C(OH)CH 2COSCoA CH 2O-CO-R’ Serine Inositol R'-CO-OCH CDP-diacyl glycerol O Glycolate HOCH 2CHO ß-OH-ß-Methylglutaryl-CoA CH2COO CH3C(OH)CH 2CHO OXALOACETATE OOCCH(OH)CH 2COO 2-Aceto-22-Oxo-3-methyl 2:3-Di-OHhydroxy- 3-methylvalerate valerate butyrate CH3 CH 3 CH3COCHCOSCoA CH3CH(OH)CHCOSCoA CH3 CH3CH=CHCOSCoA C(OH)CH(OH)COO CH3CH2 P OCH 2C(CH 3)2CH(OH)CONHCH 2CH2COO CH3CH2 CH3CH2 ISOLEUCINE CH 3 COO P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCHCH 2SH 4-P-Pantothenate Cysteine 8 CH2COO C(OH)COO CH2COO 4-P-Pantothenylcysteine CH 3CH2COSCoA P H O S P H O L I P I D S CH 2O-CO-R R'-CO-OCH O O CH2O-CO-R R'-CO-OCH O CH2O-CO-R CH2O-PO CH 2CHOHCH 2OH HOOC-COOH O HCO-CO-R Oxalate MALATE OOCCH=CHCOO CH2 O-POCH 2CH(OH)CH 2 O-P-OCH 2 O O + CH2OPO CH2CH2N(CH 3)3 O CH 2 O-CO-R R'-CO-OCH O O R'-CO-OCH + + CH2OPO CH2CH2N(CH 3)3 CH2OPOCH2CH2N(CH 3)3 O O CH2OCH=CHR Phosphatidyl ethanolamine CEPHALIN + CH 2O P OCH 2CH2 NH 3 Cardiolipin - OPhosphatidylglycerol Glycol aldehyde + HOCH 2CH 2NH 3 CITRATE HOOCCHO 4. .2 1.3 Propanoyl-CoA CH3 2-Methylaceto2-Methyl-3- 2 Methylbutyryl1.1.1.35 acetyl-CoA hydroxyCoA butyryl-CoA COOH CH3CH 2CHCOSCoA P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH 2SH 4-P-Pantetheine CDP-Ethanolamine CH2O-CO-R HOCH O + CPP- OCH 2CH2 NH3 Ethanolamine-P CH2OH HOCH O + CH2OPO CH2CH 2N(CH 3) O + POCH2CH2 NH3 Mevaldate FUMARATE COOH (CH3)2CHCHCH(OH)COO Glyoxylate CHOHCOO CHCOO CH2COO 4.3 .1. 1 + OOCCH 2CH(NH 3)COO (CH3)2CHC(OH)CH 2COO Ethanolamine CH3COCH 2CH2N(CH 3 )3 2-Isopropylmalate 3-Isopropyl- Oxoleucine malate (CH3)2CHCH 2COCOO + (CH3)2CHCH 2 CH(NH 3)COO LEUCINE ADP- OCH2 C(CH 3)2CH(OH)CONHCH 2CH2CO NHCH 2CH2SH Dephospho-Coenzyme A OOC-CH-COSCoA - Lysolecithin Glycerophosphocholine + P OCH 2CH2 N(CH 3)3 3.1 .4.2 2 Acetylcholine CH C(OH)CH CH OH 3 2 2 Mevalonate CH COO ISOCITRATE 5-Amino levulinate Choline plasmalogen Serine + NH 3 CH 3(CH2)14COCHCH 2OH LECITHIN + CPP-O CH2CH2N(CH 3)3 Dehydrosphinganin Gangliosides NHAcyl + CH3(CH2)12CH=CHCH(OH)CHCH 2O PO CH2CH2N(CH 3)3 O Sphinganin 4-Sphingenin UDP-Sugars Acyl-CoA UDP-Galactose O NHCOR + NH 3 CH3(CH2)14CH(OH)CHCH 2OH + NH 3 CH3(CH2)12CH=CHCH(OH)CHCH 2OH .3 2.7.8 CDP-choline 2 Choline-P + HOCH 2CH2N(CH 3)3 CH2COO CO2 SUCCINATE GTP GDP+Pi OOCCH 2CH2COO ASPARTATE 1.2.1 .16 Methylmalonyl-CoA 2.7 . 2.4 + P OOCCH 2CH(NH3)COO CH3 3-Methylglutaconyl-CoA H C N OOCCH 2C = CHCOSCoA 3-Methylcrotonyl-CoA H2 C N CH3 CH3C = CHCOSCoA Isovaleryl-CoA (CH3)2CHCH 2COSCoA P-ADP- OCH 2 C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH2SH Coenzyme A + NH3 OOCCH-CH 2CH2CH2CHCOO + NH 3 CHOLINE SUCCINYL-CoA -OOCCOCH CH COO2 2 - OOCCH CH COSCoA 2 2 Aspartyl-P 1 .2 .1. + NH 3 CH3(CH2)12CH=CHCH(OH)CHCH 2O- Galactose CH3C(OH)CH 2CH2OPP Diphosphomevalonate 11 Psychosine NHCOR 2-OXOGLUTARATE NADH+H + NAD + Aspartyl Succinic Semialdehyde semialdehyde OOCCH 2CH2CHO + OHCCH 2CH (NH3)COO HC OOCC CH 2 CH-COO H 2C OOCC CH2 CH-COO OOCCH 2CH2CONH OOCCH 2CH2CONH OOCCOCH 2CH2CH2CH-COO OOCCHCH 2CH2CH 2CH-COO + NH3 A M I N O A C I D S Pyruvate decarboxylase Oxaloacetate decarboxylase Acetoacetate decarboxylase Malonyl-CoA decarboxylase Aspartate 1-decarboxylase Aspartate 4-decarboxylase Glutamate decarboxylase Ornithine decarboxylase Diaminopimelate decarboxylase Phosphoribosylaminoimidazole carboxylase Histidine decarboxylase Orotidine-5’-phosphate decarboxylase Tyrosine decarboxylase Aromatic-L-amino-acid decarboxylase Sulfoalanine decarboxylase Phosphoenolpyruvate carboxykinase (GTP) Diphosphomevalonate decarboxylase Dehydro-l-gulonate decarboxylase Phosphopantothenoylcysteine decarboxylase Uroporphyrinogen decarboxylase Ribulose-bisphosphate carboxylase Methylmalonyl-CoA decarboxylase Phenylpyruvate decarboxylase Aminocarboxymuconatesemialdehyde decarboxylase Indole-3-glycerol-phosphate synthase Phosphoenolpyruvate carboxykinase (ATP) Adenosylmethionine decarboxylase Phosphatidylserine decarboxylase 2-Oxoglutarate decarboxylase Threonine aldolase Ketopantoaldolase Fructose-bisphosphate aldolase 2-Dehydro-3-deoxyphosphogluconate aldolase Isocitrate lyase Malate synthase Hydroxymethylglutaryl-CoA lyase Hydroxymethylglutaryl-CoA synthase Citrate (si)-synthase ATP citrate (pro-S)-lyase 4-Hydroxy-2-oxoglutarate aldolase Acetolactate synthase N-Acylneuraminate-9-phosphate synthase Homocitrate synthase Citramalate lyase Anthranilate synthase Tryptophanase Fumarate hydratase Aconitate hydratase Citrate dehydratase Dihydroxy-acid dehydratase 3-Dehydroxyquinate dehydratase Phosphopyruvate hydratase (enolase) l-Serine dehydratase Threonine dehydratase Enoyl-CoA hydratase Methylglutaconyl-CoA hydratase Imidazoleglycerol-phosphate dehydratase Tryptophan synthase Cystathionine B-synthase Porphobilinogen synthase 3-Isopropylmalate dehydratase dTDPglucose 4,6-dehydratase GDPmannose 4,6-dehydratase Urocanate hydratase Prephenate dehydratase Dihydrodipicolinate synthase 3-Hydroxybutyryl-CoA dehydratase Crotonoyl-[acyl-carrier-protein] hydratase 3-Hydroxyoctanoyl-[acyl-carrier protein] dehydratase 3-Hydroxydecanoyl-[acyl-carrier protein] dehydratase 3-Hydroxypalmitoyl-[acyl-carrier protein] dehydratase Uroporphyrinogen-III synthase 2-Oxopent-4-enoate hydratase Threonine synthase Cysteine synthase O-Succinylhomoserine (thiol)-lyase Aspartate ammonia-lyase Methylaspartate ammonia-lyase Histidine ammonia-lyase Phenylalanine ammonia-lyase Argininosuccinate lyase Adenylosuccinate lyase Cystathionine g-lyase Cystathionine ß-lyase D-Cysteine desulfhydrase Adenylate cyclase 3-Dehydroquinate synthase Chorismate synthase Ferrochelatase 2, 3-Dihydrodipicolinate Piperideine2, 6-dicarboxylate Acyl-CoA Cerebroside CH3 CH2 Glycine + H2NOCCH 2CH (NH3) COO + (CH3)3NCH2CH(OH)CH 2COO Asparagine Carnitine OH + + (CH3)3N(CH 2)3 CH2CH(NH 3)COO N-Succinyl2-amino-6-oxopimelate 6 N-Succinyl-2, 6 diaminopimelate Diaminopimelate SPHINGOMYELIN - CH3(CH2)12CH=CHCH(OH)CHCH 2OH Ceramide CH3(CH2)12CH=CHCH(OH)CHCH 2O- Galactose CH3C-CH2CH2OPP 2-AMINO ACID I Fe--S + R-CH(NH3) COO OOCCH 2CH 2CH2COSCoA N -Trimethyl3-OH-lysine 6 + + (CH3)3N(CH 2)3 CH2CH(NH 3)COO + + (H3N)(CH2)4 CH(NH 3)COO N -Trimethyllysine LYSINE .7 5.1.1 0 .2 4.1.1 - 10 Isopentenyl-PP (C5) I S O P R E N O I D S S T E R O I D S P O R P H Y R I N S Lycopene (C40) To Brain - VISION Phytoene (C40) Dimethylallyl-PP (C5) CH 3 CH3 CH3C = CHCH 2OPP FMN 4H 2H+ + TR 2.6.1.- Glutaryl-CoA OOCCH 2CH2CH2COCOO 2-Oxoadipate + OOCCH 2CH2CH2CH (NH3) COO AN ß-CAROTENE (C40) Metarhodopsin COO- hv O CH3 Rhodopsin CH3O CH3O CH3C= CHCH 2 CH2C= CHCH 2OPP CH2OPP 4H + 2e- FMNH 2 SA MI N 2-OXO ACID AT IO N + OOCCH 2CH 2CH (NH3) COO R-CO-COO 4-Aminobutyrate (GABA) H2N(CH 2)3NH(CH2)4NH (CH2)3NH2 OOCCH 2CH2CH2NH2 2-Aminoadipate 2-Aminoadipate semialdehyde Adenosyl + + OHCCH 2CH2CH2CH (NH3) COO COO NH CHCH 2CH2COO + CH 2CH2CH2CH2CH (NH3) COO Saccharopine CH3-SCH 2CH2CHNH 2 2H+ Mitochondrial Outer Membrane Mitochondrial Intermembrane Space 4.1 2.7.2 .11 5 .1.1 Spermine S-Adenosylmethyl thiopropylamine (Decarboxylated SAM) L E G Carbohydrates Biosynthesis E N D Geranyl-PP (C10) Opsin CHO Geranyl-geranyl-PP n Retinoate O Ubiquinone (Coenzyme Q) (C20) UQ UQH2 II Fe--S FAD SUCCINATE FUMARATE NO3 NO2 N2 _ GLUTAMATE + POOCCH2CH 2CH(NH3) COO H2N(CH 2)4NH (CH2)3NH2 Degradation Degradation Degradation Degradation trans-Retinal Light 11-cis-Retinal CHO Menaquinone Plastoquinone O HO CH 3 O Phytol (C20) CH3 O CH3 CH2OH OPP CH2 2H+ III 2H+ Glutamyl-P Amino Acids Lipids Spermidine Biosynthesis ISOMERASES Ribulose-phosphate 3-epimerase UDPglucose 4-epimerase l-Ribulose-phosphate 4-epimerase UDPglucuronate 4-epimerase UDP-N-acetylglucosamine 4-epimerase UDPglucuronate 5´-epimerase 5 1.3.13 dTDP-4-Dehydrorhamnose 3,5-epimerase UDP-N-acetylglucosamine 2-epimerase Methylmalonyl-CoA epimerase Maleylacetoacetate isomerase Retinal isomerase Retinol isomerase Triose-phosphate isomerase Arabinose isomerase l-Arabinose isomerase Xylose isomerase Ribose-5-phosphate isomerase Mannose-6-phosphate isomerase Glucose-6-phosphate isomerase N-(5´-Phospho-d-ribosylformimino)5-amino-1-(5´´-phosphoribosyl)4-imidazolecarboxamide isomerase Isopentenyl-diphosphate ³-isomerase Prostaglandin-E synthase Thromboxane-A synthase Phosphoglycerate mutase Phosphoglucomutase Phosphoacetylglucosamine mutase Phosphomannomutase Glutamate-1-semialdehyde 2,1-aminomutase Methylmalonyl-CoA mutase Chorismate mutase 5.4 99.7 Lanosterol synthase myo-Inositol- l-phosphate synthase LIGASES Mitochondrial Inner Membrane _ NH+ 4 ATP CO2 H2NCH2CH2CH2CH2NH2 Biosynthesis Biosynthesis Retinol esters + H2NOCCH 2CH2CH (NH3) COO CH2OH CH 3 Farnesyl-PP (C15) trans-Retinol (Vitamin A) Dark 11-cis-Retinol CH2OH Phylloquinone (Vitamin K) α-Tocopherol (Vitamin E) 2H+ Fe-S and 2eCytochromes Cyt.c Cu and Cytochromes M I TO 2H+ MITOCHONDRIAL MATRIX 1.1 .1 8.6 Glutamine + OHCCH 2CH 2CH(NH3) COO Purines & Pyrimidines Glutamic semialdehyde Putrescine CH2 CH2 CH N CHCOO Vitamins, Co-Enzymes & Hormones Pyruvate Glyoxylate OOCCH(OH)CH 2COCOO CH2 CHCOO CH3COCOO OHCCOO Pentose Phosphate Pathway Photosynthesis Dark Reactions Human Metabolism is identified as far as possible by black arrows STEROIDS Progesterone HO H IV 2H+ Carbamoyl-P H2NCOOP + H 2NCONHCH 2CH2CH2CH(NH3) COO HO H HO H H HO H 2H+ Lanosterol COOCH2 -OOC H 2C H 2C H 2C 2H+ H2O 3H + CITRULLINE Pyrroline-5carboxylate CH2 Pregnenolone CHLOROPHYLL H3 C HC CHOLESTEROL CH2 CH H C N Fe N H3 C CH2 CH2 COOC H N CH3 CH2 CH2 COOH3 C CH CH3 CH2 CH H3 C H2 C Desmosterol CH2 CH H2 C N H H N C H2 CH2 CH3 CH2 CH2 COOCH3 CH 2 CH H3 C Zymosterol COOCH2 CH2 N H H N H2 C N H H N C H2 CH3 COOCH2 CH2 CH2 CH3 CH2 CH2 COO- Squalene (C30) CH2 H 2 C N H H N CH2 CH2 COOC H2 N H H N COOCOO-OOCCH CH COCH NH CH2 2 2 2 2 CH2 CH2 CH2 CH2 CH2 CH2 IA Pi ADP ATP + H2NCH2CH2CH2CH (NH3) COO CH2 4-Hydroxy2-oxoglutarate Biosynthesis Degradation Small numbers refer to the IUBMB Enzyme Commission Reference Numbers for Enzymes The "BACKBONE" of metabolism involves GLYCOLYSIS, the TCA CYCLE and OXIDATIVE PHOSPHORYLATION. It is a major source of energy (ATP) and is the origin and termination of most of the pathways. GLYCOLYSIS occurs in the CYTOPLASM. The TCA CYCLE is in the MITOCHONDRIAL MATRIX. OXIDATIVE PHOSPHORYLATION (ATP SYNTHESIS) spans the MITOCHONDRIAL INNER MEMBRANE. This last part has been redesigned to illustrate the activation of ATP-synthase and formation of ATP - driven by the electromotive translocation of protons across the mitochondrial inner membrane. A similar compartmentation occurs in the chloroplast, where light-driven proton translocation across the inner thylakoid membrane initiates synthesis of the ATP necessary for Photosynthesis. In both cases flow of electrons and protons is shown in red or blue arrows 1H+ ORNITHINE H2NCONH 2 OOCCHCH 2COO N + H2NCNHCH 2CH 2CH2CH(NH3) COO PROLINE HOCH H2C N H CH2 CHCOO NH COMPARTMENTATION + OOCCH(OH)CH 2CH(NH 3)COO N N H H N 5-Amino levulinate COOCH2 CH2 N NE R UREA ME HEMOGLOBIN H2 C MB -OOC H2 C H2 C RAN E Glycine + H3 C CH2 CH2 COO- + H2NCNHCH 2CH2CH2CH (NH3) COO NH2 NO Argininosuccinate 4-Hydroxyglutamate HOCH HC CH2 CHCOO CH2 CH2 COO- - OOC COO- N H RO TO N ARGININE S 1H+ 3H + HYDROXY PROLINE HN C NH CO CH 2 N CH3 + NH 2 3-Hydroxypyrroline5-carboxylate N HEME Protoporphyrinogen Coproporphyrinogen COO- H2 N + NH2 IX III III Porphobilinogen ATP ADP Pi + NH2 Electron Flow Proton Flow Guanidoacetate H2NCNHCH 2COO H2NCN(CH 3)CH2COO Creatine P- HNCN(CH 3)CH2COO P-Creatine Creatinine Some other pathways occurring in the mitochondria are identified by a pale yellow background Long-chain-fatty-acid-CoA ligase Aspartate—ammonia ligase Glutamate—ammonia ligase Aspartate—ammonia ligase (ADP-forming) NAD+ synthetase Pantoate—ß-alannine ligase Glutamate—cysteine ligase Glutathione synthase Phosphopantothenate—cysteine ligase Phosphoribosylaminoimidazolesuccinocarboxamide synthase UDP-N-Acetylmuramoyl-l-alanyld-glutamate—lysine ligase UDP-N-acetylmuramate—alanine ligase UDP-N-acetylmuramoylalanine— d-glutamate ligase UDP-N-acetylmuramoylalanyld-glutamyl-lysine—d-alanyl-d-alanine ligase UDP-N-Acetyl muramoylalanyl-dglutamate—2,6-diaminopimelate ligase Phosphoribosylglycinamidine cyclo-ligase GMP synthase CTP synthase Formate—tetrahydrofolate ligase Adenylosuccinate synthase Argininosuccinate synthase Ribose-5-phosphate—ammonia ligase Phosphoribosylamine—glycine ligase Carbamoyl-phosphate synthase (ammonia) Formate—dihydrofolate ligase NAD+ synthetase (glutamine-hydrolysing) GMP synthetase (glutamine-hydrolysing) Phosphoribosylformylglycinamidine synthetase Asparagine synthase (glutamine-hydrolysing) Carbamoyl-phosphate synthase (glutamine-hydrolysing) Pyruvate carboxylase Acetyl-CoA carboxylase Propionyl-CoA carboxylase Methylcrotonoyl-CoA carboxylase CH TRA N SLO CAT ON DR L I ED P Cytoplasm Cytoplasmic Membrane Enzymes available from Sigma Enzymes available from Sigma Enzymes available from Sigma ...
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This note was uploaded on 11/26/2009 for the course BIO 361 taught by Professor Lake during the Fall '08 term at SUNY Stony Brook.

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