Mapa Metabólico

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Metabolic Pathways BLOOD GROUP ALGINATES O-ANTIGENS HYALURONIC ACID DERMATAN STARCH SUBSTANCES PEPTIDOCHONDROITIN PECTIN INULIN CELLULOSE GLYCAN CH OHCHITIN COO - O COO - 6.3.2.7-10 6.3.2.13 HO O 2.4.99.7 CH2OH O OPC OPPU CH3CH NHAC O CHOH CHOH CH2OH HO HO 1.1.1.158 3.1.3.29 N-Ac-Neuraminate CH2OH O HO O CH2 C (Sialate) COO CH2OH O HO HO OH 2.7.1.7 Mannose-1-P HO OH OPPU UDP-N-Ac-Glucosamine COO HOCH 2 OH H OH OH C C C H OH H COO - C H C C H H H O HOCH 2 OH OH C C C H CO H OH H HOCH 2 C OH C HOCH 2 OH H H OH H OH C H C CHO OH H L-Xylose OH H HOCH 2 C HOCH 2 C H CH2OH C C CHO H H OH 1.1.1.10 L-Arabinose H OH H C C H H C C OH 2.7.1.47 HOCH 2 C C H H C C H OH H OH H CO HOCH 2 C H HOCH 2 CO CH OH 2 PQ 1e- P700 PC H OH C C POCH 2 4.1.2.- H H H POCH 2 C POCH C C CHO POCH2 HO C C H H H OH C C C P-Ribosyl amine C CO CH2OP Pi Dihydroxyacetone-P POCH 2CHOHCOOP α α 3 α β ADP HO COO L I P I D COSCoA Oleoyl-CoA 1.14.99.5 CH3(CH2)14COS-ACP 9 CH 3(CH2)2CH 2CH2COSACP 3-Enoyl-ACP Hexanoyl-ACP 4.2.1. .60 4.2.1 CH3(CH2)2CH=CHCO-S-ACP 2, 3-Hexenoyl-ACP CH3CH=CHCO-S-ACP 1.3.1.9 Butanoyl-ACP Crotonoyl-ACP CH3(CH2)n+2COS-CoA 6.2.1.3 FATTY ACID 3.1.2.20 2.3.1.15 Carnitine O-Acyl-carnitine L I P I D CH2O-CO-R" Triacylglycerol 2.3.1.20 glycerol 3.1.3.4 2.7.1.107 ACYL-CoA 1.3.99.3 (Mitochondria) CH3(CH2)2CH2CH2COSCoA Hexanoyl-CoA CH3CH2CH2COSCoA CH3(CH2)2CH=CHCOSCoA 4.2.1.17 CH3CH=CHCOSCoA 4.2.1.55 2, 3-Hexenoyl-CoA 1.3.99.2 Butanoyl-CoA 4.2.1.17 2, 3-Enoyl-CoA 1.3.99.3 Crotonoyl-CoA 3-OH-Hexanoyl-CoA CH3CH(OH)CH 2COSCoA CH 3CH2CH 2CH2COSCoA CH3CH2CH=CHCOSCoA CH3CH2CH(OH)CH 2COSCoA Pentenoyl-CoA Pentanoyl-CoA OH O - R'-CO-OCH COO O + CH 2O PO CH 2CHNH 3 PHOSPHATIDYL SERINE O 2.7.8.8 Phosphatidyl ethanolamine CEPHALIN O + POCH2CH2 NH3 2.7.7.14 CDP-Ethanolamine LECITHIN .3 2.7.8 + NH 3 CH3(CH2)12CH=CHCH(OH)CHCH 2OH UDP-Sugars Acyl-CoA Ceramide 3.1.4.12 Geranyl-PP CH3 trans-Retinal (C20) Ubiquinone 2.5.1.10 (Coenzyme Q) 5.2.1.3 Light 1.1.1.105 11-cis-Retinal Phytol (C20) Plastoquinone CH2OH O 11-cis-Retinol Dark (Vitamin A) CH 3 CH2OH 5.2.1.7 trans-Retinol HO O CH3 (Vitamin K) (C15) CH CH2 CH H2 C C H CH2 COO- HEME CH3 CH N H N H H N H N H3 C C H2 CH2 H3 C CH2 N H N H H N H N H3 C C H2 CH2 CH2 CH2 CH2 CH2 CH2 COO- COO- CH2 CH2 COO- COO- 4.99.1.1 Protoporphyrinogen 1.3.3.3 - CH2 Coproporphyrinogen N H N H H N H N H 2C OOC CH2 C H2 Brazil SIGMA-ALDRICH BRASIL LTDA. Free Tel: 0800 701 7425 Tel: (+55) 11 3732 3100 Fax: (+55) 11 5522 9895 Canada SIGMA-ALDRICH CANADA LTD. Free Tel: 1800 565 1400 Free Fax: 1800 265 3858 Tel: (+1) 905 829 9500 Fax: (+1) 905 829 9292 sigma-aldrich.com/metpath Chile SIGMA-ALDRICH QUIMICA LIMITADA Tel: (+56) 2 495 7395 Fax: (+56) 2 495 7396 China SIGMA-ALDRICH (SHANGHAI) TRADING CO. LTD. Free Tel: 800 819 3336 Tel: (+86) 21 6141 5566 Fax: (+86) 21 6141 5567 Czech Republic SIGMA-ALDRICH spol. s r. o. Tel: (+420) 246 003 200 Fax: (+420) 246 003 291 CH2 COO- COO- 4.1.1.37 Uroporphyrinogen Denmark SIGMA-ALDRICH DENMARK A/S Tel: (+45) 43 56 59 00 Fax: (+45) 43 56 59 05 Finland SIGMA-ALDRICH FINLAND OY Tel: (+358) 9 350 9250 Fax: (+358) 9 350 92555 France SIGMA-ALDRICH CHIMIE S.à.r.l. Free Tel: 0800 211 408 Free Fax: 0800 031 052 Tel: (+33) 474 82 28 00 Fax: (+33) 474 95 68 08 4.3.1.8 4.2.1.75 CH 2 CH 2 H2 C H2 C CH2 ©2003 International Union of Biochemistry and Molecular Biology www.iubmb.org 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 5-Amino- -OOC CH2 COO- H2 O COOlevulinate CH2 CH2 (C30) CH2 H2NCH2C=O CH2 CH2 H 2C CH3 CH2 CH2 H 2 C H 2C CH2 CH2 1.3.3.4 -OOC Squalene ADP + IV 1/ O 2 2 COOCH2 COOCOO- CH2 CH2 CH2 COO- Lanosterol 5.4.99.7 1.14.99.7 COOCOOCH3 H2 C H2 C CH3 H Zymosterol CH2 CH3 CH 2 H2 C H3 C N H β 2 Pi AT E H+ H+ H+ β H+ H+ Porphobilinogen 3 α δ CH3 OOCCH 2C = CHCOSCoA HC OOCC H C H+ H+ N2 ADP Pi ATP 2.7.1.33 P OCH 2C(CH 3)2CH(OH)CONHCH 2CH2COO 4-P-Pantothenate Cysteine 6.3.2.5 COO P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCHCH 2SH 4-P-Pantothenylcysteine 1.2.1.25 CH3CH 2CHCOSCoA 4.1.1.36 P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH 2SH 4-P-Pantetheine Y RGONIC REACTIO N 1.4.1.9 OOCCH 2CH2CH2COCOO 2-Oxoadipate 2.7.2. NH2 CH 2.6.1.13 Guanidoacetate Creatine CH3COCOO + NH2 OHCCOO 4.1.3.16 OOCCH(OH)CH 2COCOO CH2 CHCOO 1.14.11.2 HOCH 4-Hydroxy2-oxoglutarate Biosynthesis Degradation 4-Hydroxyglutamate N H NH N CH3 CO CH 2 Degradation Biosynthesis Photosynthesis Dark Reactions Human Metabolism is identified as far possible by black arrows 1.5.1.12 Degradation Biosynthesis COMPARTMENTATION + OOCCH(OH)CH 2CH(NH 3)COO CHCOO HYDROXY PROLINE HN C Biosynthesis Degradation Vitamins Co-enzymes & Hormones 2.6.1.23 CH2 H2C P- HNCN(CH 3)CH2COO 3.5.2.10 Purines & Pyrimidines Pentose Phosphate Pathway PROLINE Argininosuccinate P-Creatine Lipids Pyruvate Glyoxylate CH2 OOCCHCH 2COO N + H2NCNHCH 2CH 2CH2CH(NH3) COO 2.7.3.2 Amino Acids Biosynthesis Degradation NH H2NCN(CH 3)CH2COO LEGEND CHCOO 1.5.99.8 CH2 1.5.1.2 4.3.2.1 2.1.1.2 Saccharopine Carbohydrates Biosynthesis Degradation Pyrroline-5carboxylate 6.3.4.5 + NH2 2 + CH 2CH2CH2CH2CH (NH3) COO + S-Adenosylmethyl thiopropylamine N ARGININE H2NCNHCH 2COO A C I D S CH3-SCH 2CH2CHNH 2 2.5.1.16 2.1.3.3 NO A M I N O COO NH CHCH 2CH2COO 1.5.1.9 Putrescine Glutamic semialdehyde 1.14.13.39 LYSINE + OHCCH 2CH2CH2CH (NH3) COO 2-Aminoadipate 1.2.1.31 2-Aminoadipate 2.6.1.39 semialdehyde H2NCH2CH2CH2CH2NH2 + OHCCH 2CH 2CH(NH3) COO 4.1.1.17 3.5.3.6 N6-Trimethyllysine + OOCCH 2CH2CH2CH (NH3) COO .7 5.1.1 20 4.1.1. 1.5.1.7 - 10 + H2N(CH 2)4 CH(NH 3)COO + + (CH3)3N(CH 2)3 CH2CH(NH 3)COO 1.14.11.8 Spermidine 1.2.1.41 + H 2NCONHCH 2CH2CH2CH(NH3) COO 3.5.3.1 + NH3 OOCCH-CH 2CH2CH2CHCOO + NH 3 OOCCHCH 2CH2CH 2CH-COO + NH3 N-Succinyl- 2.6.1.17 N-Succinyl-2, 6 3.5.1.18 Diamino2-amino-6-oxodiaminopimelate pimelate pimelate H2N(CH 2)4NH (CH2)3NH2 CH2 CH2 + H2NCNHCH 2CH2CH2CH (NH3) COO Coenzyme A OOCCH 2CH2CONH OOCCH 2CH2CONH OOCCOCH 2CH2CH2CH-COO 2.5.1.22 + 6.3.5.5 UREA 2.7.1.24 P-ADP- OCH 2 C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH2SH (CH3)2CHCH 2COSCoA Isovaleryl-CoA Adenosyl 11 POOCCH CH CH(NH ) COO 3 2 2 H2NCONH 2 2.1.4.1 Dephospho-Coenzyme A (Decarboxylated SAM) Glutamine H2NCOOP ADP- OCH2 C(CH 3)2CH(OH)CONHCH 2CH2CO NHCH 2CH2SH LEUCINE 1.2.1.25 CH2 CH-COO N6-Trimethyl3-OH-lysine Spermine + H2NOCCH 2CH2CH (NH3) COO ATP CO2 Glycine + + NH H2 C 2.7.7.3 + (CH3)2CHCH 2 CH(NH 3)COO 2.6.1.6 + + (CH3)3N(CH 2)3 CH2CH(NH 3)COO 15 ORNITHINE s H 2C OOCC H2N(CH 2)3NH(CH2)4NH (CH2)3NH2 2.1.3.3 F0 nit CH 3 1.3.99.10 N 1.14.11.1 Glutaryl-CoA 3.5.1.2 6.3.1.2 NH4+ .7.1 1.7 .6.4 1.6 .1 .6 18 6.3.4.16 1. F1 10 c-sucb-u 6.3.2.1 PANTOTHENATE CH3CH2 ISOLEUCINE 3-Methylcrotonyl-CoA CH 2 CH-COO 1. 1. 4. 1.4.1.14 β H+ CH3 CH3C = CHCOSCoA N OOCCH 2CH 2CH2COSCoA (GABA) + H2NCH2CH2CH2CH (NH3) COO ε 6.4.1.4 3-Methylglutaconyl-CoA 4-Aminobutyrate GLUTAMATE AT I ON NO2- (CH3)2CHCH 2COCOO OOCCH 2CH2CH2NH2 + OOCCH 2CH 2CH (NH3) COO H+ H+ H+ H+ D PROTONS E NDE AαT H+ + H+ 1.1.1.169 HOCH2 C(CH3)2CH(OH)CO NHCH 2CH2COO + CHCH(NH 3)COO COOH (CH3)2CHCHCH(OH)COO CITRULLINE γ γ α X ATP P +1 P i a 4.2.1.24 N H H2 N CH3CH(OH)CHCOSCoA Oxopantoate Pantoate ß-Alanine 3.5.1.22 1.2.1.25 CH3 CH3 CH3CH=CHCOSCoA HOCH 2 C(CH 3)2COCOO HOCH 2 C(CH 3)2CH(OH)COO CH3CHCO-SCoA 2.6.1.32 (SAM) 3)COO CH 3 CH3CH2 2.5.1.6 S-Adenosyl methionine Glutathione 2-3-Dihydroxy 4.2.1.9 2-Oxo- 1.4.1.8 VALINE isovalerate isovalerate CHCOCOO 1.2.1.32 CH3 2.6.1.32 CH3 2SO 4 + CH 3 SCH CH CH(NH )COO 3 + 2 2 2.1.1.10 2.1.1.20 4.1.2.12 CH3 + CHCH(NH CH3 4.3.1.3 CH2SH + OOCCH(NH 3)CH2CH2CONHCHCONHCH 2COO Bile Acids CH2 = CCOSCoA 4.2.1.19 Glycine .3 CHCOCOO N CHCOO Adenosyl 6.3.2 CH3 CH METHIONINE Adenosyl CH3 CH2COCH2OP NH + CH 3 SCH CH CH(NH )COO 2 2 3 2.1.1.13 2.1.1.14 γ-Glutamylcysteine C H Imidazole acetol-P 2.7.7.4 (APS) HCHO C (OH)CH(OH)COO CH3 CH 3 Carnitine Carbamoyl-P β C H3 C CH CH N Fe N ATP N NH CH Adenylylsulphate CH2SH + OOCCH(NH 3)CH2CH2CONHCHCOO CH C Urocanate S-Adenosyl homocysteine Taurine CH3 2.6.1.19 2-OXO ACID 1.6.6.1 1.7.99.4 F1 TRA N S L O CH3 HO COO- CH2 N HC Desmosterol CHLOROPHYLL CH2 H C 2H 1.9.3.1 H HO N + SCH 2CH2CH(NH 3)COO 2.3.1.46 CH3CH2 + OHCCH 2CH (NH3)COO 4.1.1.70 2.6.1.- IN NO3- or ting ATP nsp 3.6.1.34 synt h tra oscp AD HEMOGLOBIN H3 C H HO CHOLESTEROL Pregnenolone CH + .2 HO3SCH 2CH2NH2 C HC C CH 3-Hydroxy- 4.2.1.17 Methyl 1.3.99.3 Isobutyryl-CoA Isobutyryl-CoA acrylyl-CoA Glutamyl-P F6 2eH HO 1 2-AMINO ACID δ 2H+ CuB Heme a3 Progesterone .1.1 1.3.99.7 M 2H+ Heme a STEROIDS 1.2 R-CO-COO +- 6.3.2 9 1.8.1.3 OOCCH 2CH2CHO Aspartyl 4.2.1.52 2, 3-Dihydro-1.3.1.26 PiperideineSemialdehyde dipicolinate 2, 6-dicarboxylate Succinic semialdehyde OH 1.4.1.2 2.5.1.21 (Vitamin E) Aspartyl-P UQ 1.10.2.2 Farnesyl-PP CH 3 α-Tocopherol Phylloquinone _ UQ. CuA CuA CH3 2H+ e as O 2.3.1.76 3.1.1.21 Cyt.c OPP CH2 CH2OH Menaquinone CHO 1.1.1.105 1e- Glutamate 3.3.1.1 H C OH OH HN 2.6.1.9 4.2.1.49 Homocysteine H P OCH 2 C C H CHCH 2CH2COO + HSCH 2CH2CH(NH 3)COO 4.4.1.8 3-Isopropyl- 1.1.1.85 Oxoleucine 4.2.1.33 malate 4.2.1.18 + R-CH(NH3) COO 1eCyt.bH Cyt.c1 2UQ (C10) Geranyl-geranyl-PP n O CHO 1.2.1.36 CH3C= CHCH 2 CH2C= CHCH 2OPP CH2OPP 5-Aminolevulinate RPPP CYTIDINEtriphosphate Imidazole glycerol-P CH2CH(NH 3)CH2OP NH CH 2.7.1.25 4.2.1.22 Cystathionine HOCH 2CHCOS-CoA- + (CH3)3NCH2CH(OH)CH 2COO A Retinoate CH3O O 2.5.1.1 CH3 CH 3 2.5.1.29 6.3.4.2 CH 2.7.4.6 CH C N P Y R I M I D I N E S (CTP) NH CH Imidazolone propionate Phosphoadenylylsulphate CH3 3.1.2.4 COOH Asparagine NS CH3O Opsin (C5) 2.5.1.32 Rhodopsin 2e- 2UQ_ . III 2eFe-S Cyt.bL N C(OH)CH(OH)COO 2-Isopropylmalate + H2NOCCH 2CH (NH3 COO TRA hv 1.13.11.21 COO- Retinol esters CH3C = CHCH 2OPP 4H+ Dimethylallyl-PP (C40) To Brain - VISION (C5) 1.1.1.86 + P OOCCH 2CH(NH3)COO 5.4.99.2 Glycine UQH2 1.10.2.2 3.1.3.15 3.5.2.7 + CH2CH(NH 3)COO + SCH 2CH2CH(NH 3)COO 1.1.1.3 (CH3)2CHC(OH)CH 2COO 1.1.1.3 5.1.99.1 2.3.1.37 2UQH2 6.4.1.3 4.2.1.18 1.2.1.16 SUCCINATE 2H+ C N CDP NH 2 N RPPP Histidinol-P 2-Methylaceto-1.1.1.35 2-Methyl-3-4.2.1.17Tiglyl-CoA 2 Methylbutyryl1.3.99.3 acetyl-CoA hydroxyCoA butyryl-CoA .4 6.3.5.4 SUCCINYL-CoA d-CDP N OC CH CH CONH 2 N NH C CH C HC N N RP CH2 HC CH 2CH(NH 3)CH2OH OC CH3 2.7.2 4.3.1.1 -OOCCH2CH2CO.SCoA CH2 Isopentenyl-PP ASPARTATE 6.2.1.4 II NH CH + HOCH 2CH2CH(NH 3)COO COO CH3 1.2.4.2 2.3.1.61 UQH2 CH3C-CH2CH2OPP CH3 Phytoene Lycopene (C40) UQ 4.1.1.33 31 1.1.1. Methylmalonyl-CoA 4.1.1.71 2-OXO- + CO OH OH CHCH 2CH2COO O-Phospho- 2.7.1.39Homoserine homoserine CH3 HOCH 2CHCOO CH 3CH2COSCoA -OOCCH2CH2COO- FAD C N 4.2.1.9 2-Aceto-22-Oxo-3-methyl 2:3-Di-OHhydroxy- 1.1.1.86 3-methylvalerate valerate butyrate 2.1.3.1 4.1.1.41 5.1.99.1 GLUTARATE 1.3.5.1 Fe-S Cyt.b C + OOCCH2CH2COOCH2CH2CH(NH 3)COO CH3COCHCOSCoA 1.1.1.41 OOCCH=CHCOO- HC NH CH Hypotaurine 3-Hydroxyisobutyrate OOC-CH-COSCoA FADH2 H Histidinol 1.1.1.23 .1.2 CH3 FUMARATE UQH2 NHCOR Cerebroside 3.2.1.46 2.4.1.47 1.3.99.7 + CH2CH(NH 3)CHO 4.1 Oxobutyrate .3.1 H P OCH 2 C DP 1.17.4.1 Propanoyl-CoA -OOCCOCH CH COO2 2 or 2H+ - O C N 2.7.4.14 Cytosine HN OC 2.4.2.9 RP Cysteate 2-Acetolactate 16 CH(OH)COOCHCOOCH2COOC 4.1.3.1 MALATE 4H+ 2H+ 4.2.1.2 d-CMP NH 2 C CH CH OC NH P-Ribulosylformimino P-Ribosylformimino 5-aminoimidazole- 5.3.1.16 5-aminoimidazolecarboxamide-R P+ carboxamide-R P + + HO3SCH 2CH(NH 3)COO CH3COC(OH)CH 3 8 NH2 N OC C NH CH C HC N N OH OH O 1.8.99.2 4.2.99.9 + POCH 2CH2CH(NH 3)COO 4.2.99.2 2.3.1. 4.2.1.3 CH3CH(OH)CH2CO.SCoA 1.6. 5.3 Diphosphomevalonate CH3(CH2)12CH=CHCH(OH)CHCH 2O- Galactose C Succinylhomoserine 4.1.3.7 CH2COOC(OH)COOCH2COO- ISOCITRATE 2H 2Fe -S (5 Clusters) 4H+ Psychosine CH3(CH2)12CH=CHCH(OH)CHCH 2OH H C HO2SCH 2CH2NH2 CITRATE + C-COO RP N NH CH 4.4.1.1 CYSTEINE COO Methylmalonyl semialdehyde Glyoxylate Cycle 1.1.1.37 CH2COO Acyl-CoA H C Histidinal HSO - 1.8.99.1 Cysteine sulphinate CH3CH2COCOO CH3 OHCCHCOO -OOCCHO FMNH2 CH3C(OH)CH 2CH2OPP + NH 3 CH3(CH2)12CH=CHCH(OH)CHCH 2O- Galactose UDP-Galactose NHCOR CHOLINE 2.7.1.32 4.1.3.2 2.7.1.36 2.7.4.2 + HOCH 2CH2N(CH 3)3 + OCH 2CH2 N(CH 3)3 Choline-P 2.4.1.23 3.5.1.23 2.4.1.62 O ß-CAROTENE (C40) Metarhodopsin 2.3.1.6 4-Sphingenin 1.1.1.102 2.7.8.3 2.7.7.15 3.1.4.12 CH COO 2 Acetylcholine CH C(OH)CH 3 2 CH2OH 3.1 .4.2 Mevalonate 3.1.4.3 CDP-choline 1.1.1.32 CH3COCH 2CH2N(CH3 )3 3.1.4.4 + CPP-O CH2CH2N(CH 3)3 Sphinganin SPHINGOMYELIN Mevaldate Ethanolamine Glycerophosphocholine I CH OC N CH RP CH N RP NH2 C CH CH N N 3.5.4.1 O C HN N C C N OC d-UMP .4 CH O C HN H2 N C (GMP) CH CH N DP 3.5.4.12 (PAPS) 4.2.1.16 4.1 4.1.3.8 I CH2COO CH3C(OH)CH 2CHO + HOCH 2CH 2NH 3 + CH2OPO CH2CH 2N(CH 3) O 3.1.1.5 2.7.8.2 + NH 3 CH3(CH2)14CH(OH)CHCH 2OH - XXX 52 2.6.1.1 NAD+ 18 FMN HS CH3COC(OH)CH 2CH3 4.2.1. 1.1.1.34 Oxalate Glycol aldehyde CH2OH - Lysolecithin HOOC-COOH HOCH 2CHO HOCH O + CH2OPO CH2CH2N(CH 3)3 2.1.1.17 O CH2OCH=CHR 2.1.1.71 CH 2 O-CO-R R-CO-OCH O 3.1.1.32 O R'-CO-OCH + + CH2OPO CH2CH2N(CH 3)3 CH2OPOCH2CH2N(CH 3)3 O O ß-OH-ß-Methylglutaryl-CoA 1.4.3.8 2.7.1.82 Ethanolamine-P CH2O-CO-R 3 2.7.8.5 O OPhosphatidylglycerol HOCH O Choline plasmalogen 1.3.1.35 Serine +NH Glycolate 1.2.1.21 CH2O-PO CH 2CHOHCH 2OH - + CPP- OCH 2CH2 NH3 2.7.8.1 HOCH 2COO H C C HC 1.1.1.23 + .8 HSCH 2CH(NH 3)COO 18 4.1.1.32 OXALOACETATE OC 1 O C 2.4.2 N H CH N RP P U R I N E S GUANOSINE-P HN OC THYMIDINE-P 1.13.11.20 4.1.3. Malonic semialdehyde 1. 1.2.1.18 -OOCCOCH COO2 NADH+H+ CH3C(OH)CH 2COSCoA O C 6.3.4.1 6.3.5.2 2.4.2. .1 C-CH3 CH 2.1.1.45 OC N DP CH CH N C C H XANTHOSINE-P 2.7.4.8 C .4.9 HN N (XMP) O 2.7 O C HN 1.1.1.205 OC 3 1.17.4 CH N RP (IMP) 3.5.4. GDP RP N C C N 6.3.4.4 Guanine C A T E C H O L A M I N E S CH N INOSINE-P 3.1.4.6 2.7.4.6 Formimino glutamate 1.6.4.1 1.1.1.39 4.1.3.4 CH2COO 1.2.3.5 1.6.5.3 Cardiolipin O + CH 2O P OCH 2CH2 NH 3 2.3.1.50 R'-CO-OCH CH2 O-POCH 2CH(OH)CH 2 O-P-OCH 2 O O R'-CO-OCH CDP-diacyl glycerol CH2O-CO-R O HCO-CO-R Glyoxylate 1.1.1.79 O Inositol 2.7.8.11 4.1.3.5 OHCCOO 2.7.7.41 O CH2O POCMP Serine CH 2O-CO-R’ CH2O-CO-R R'-CO-OCH O 4.1.1.65 CH 2O-CO-R CH 2O-CO-R R'-CO-OCH 1.3.99.7 HO OH Aspartate .1 N C O C HC 2.4.2.1 1.1 O C C NH 3.5.4.10 Adenylosuccinate Uracil HN H HN + CH3CH(OH)CH(NH 3)COO OHCCH 2COO- ACETYL-CoA NAD+ 1.3.1.2 CH C-COO NH 3.5.4.19 N 4.1.1.29 GTP CH3COSCoA H2 N HCO HN 7.4 O C HN OC O C P OCH 2 .99 THREONINE LACTATE P CH 2O-CO-R OH CH2O-PO + CH3(CH2)12CH=CHCH(OH)CHCH 2O PO CH2CH2N(CH 3)3 O Austria SIGMA-ALDRICH HANDELS GmbH Tel: (+43) 1 605 81 10 Fax: (+43) 1 605 81 20 6.4.1.1 5 2.4.2.1 d-GDP 2.4.2.4 Thymine OOC HO2SCH 2COCOO 2.6.1.18 2. 2.4.2.15 TDP O C HN OC NH CH 4.1.2.5 7 4. NH .6 Dihydrouracil CH-COO NH + HO 2SCH 2CH(NH 3)COO CH3CH(OH)COO HOH GDP CO2 1.2.4.1 2.3.1.12 3.1.3.43 NADH+H+ 4.1.3.5 3-Oxopentanoyl-CoA 3.5.2.2 RP 3.1.3. Inosine 2 3.2.2. CH A C I D S Formylamidoimidazolecarboxamide-R P 4.3.1.3 4.2 CYSTINE 4.1.1.12 .1.2 H CH2O-CO-R R'-CO-OCH O NHAcyl 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 1.1 N N C C 4.3.2.2 .7.6 CH2 CH2 OC NH CH2 HISTIDINE CH2CH2NH2 3-Sulphinyl pyruvate ALANINE 18 HC 2.7 C CH3 CH NH 1.3.1.2 CH 2.1.2.3 d-CTP GTP TTP 2.7.4 O C HISTAMINE + S-CH 2CH(NH 3)COO + S-CH 2CH(NH 3)COO .1.44 2.6.1.4 2.6 Gangliosides Argentina SIGMA-ALDRICH DE ARGENTINA S.A. Free Tel: 0810 888 7446 Tel: (+54) 11 4556 1472 Fax: (+54) 11 4552 1698 16 2.3.1.9 CH3COCH 2COSCoA Acetoacetyl-CoA CH3CH2COCH 2COSCoA 1.1.1.35 3-OH-Pentanoyl-CoA 2.3.1. 3-Oxohexanoyl-CoA 1.1.1.157 3-OH-Butanoyl-CoA 16 CH3(CH2)2COCH 2COSCoA 1.1.1.35 CH3(CH2)2CH(OH)CH 2COSCoA Dihydro thymine + CH2CH(NH 3)COO C HC + CH2CO-OCH2CH(NH 3)COO + CH3CH(NH3)COO 4.1.3. CH3COCOO- NAD ATP CO2 2.3.1. 3-Oxoacyl-CoA 0 HSO32.6.1.2 HN d-GTP .7.7 HN OC P-Ribosyl-AMP N 4.4.1.15 1.4.1.1 1.2.4.1 2.3.1.12 1.8.1.4 2.3.1.38 CH3(CH2)n COCH 2COSCoA 1.1.1.35 3-OH-Acyl-CoA NHCOCH 2CH2NH2 Acetylserine 4.4.1.15 PYRUVATE O C Fumarate 2.7 CH-CH3 CH 2 NH N C C N H 2N NH N C C N CH C HC NH RP N 2.7.7.7 2.7.7.6 O C H 2N RP Plant Pigments OOC-CH-CH 2COO 2.7.7.7 NH .1.1 4.1.1.9 CH 3CO-S-ACP Acetyl-ACP 3.1.2.11 Odd C Fatty acids CH 3(CH2)14COCHCH 2OH P O R P H Y R I N S 1.1.1.30 Acetoacetate Phosphatidate 3.6.1.31 Carnosine C C H 4.1 ATP .1.2 Malonyl-Co-A CH3COCH 2COO CH3(CH n CH(OH)CH 2COSCoA .1.3 Acetaldehyde PYRUVATE CH3(CH2)n CH=CHCOSCoA 2.3 2.1.3.2 CH3CHO 3.7 HOOCCH 2CO-SCoA CH3(CH2)n CH2CH2COSCoA Dehydrosphinganin S T E R O I D S 4.1.1.4 3.1.1.28 OH I S O P R E N O I D S CH3CH(OH)CH 2COO Acetone 3-OH-Butyrate 2.7.8.5 NH C H 2.7.1.40 2.3.1.39 CH2O P Diacyl FAT HOOCCH 2CO-S-ACP Malonyl-ACP CH N Adenine NH2 N + C C N CH C HC N N RP(PP) C CH 2CHCOO N ETHANOL ADP KETONE BODIES CH3COCH 3 R’-CO-OCH CH2OH C HC 1.2.1.4 HS CH2O P 3-P-Glycerol CH2O-CO-R CH2O-CO-R R’-CO-OCH R’-CO-OCH O-Acyl-carnitine Phosphatidyl inositol P H O S P H O L I P I D S CH2O-CO-R 3.1.1.3 2.7.1.30 Acetoacetyl-ACP 2.3.1.41 2.3.1.51 H C 4.1.1.22 1.1.1.1 CH3COCH 2COSACP 1.1.1.8 HOCH Glycerol (Cytosol) 2.3.1.7 CH2OH CH2OH HOCH CH2OH H OH OH O 2.3.1.41 3-OH-Butanoyl-ACP H C N P-enolpyruvate Tannins URIDINEDihydro Orotate Orotidine-P Uridine-P UDP 4.1.1.23 (UMP) 2.7.4.4 2.4.2.10 2.7.4.6 triphosphate orotate 1.3.1.14 3.5.2.3 P-Ribosyl-ATP Glycerate CH2=C(OP ) COO CH3(CH2)2COCH 2COSACP 1.1.1.100 H P OCH2 C 2.4.2.17 CH 3(CH2)6COCH 2COSACP 3-Oxo-Hexanoyl-ACP CH3CH(OH)CH 2COS-ACP R-CH2COO P-Hydroxypyruvate 4.2.1.11 C H 2N ADENOSINE-P O C O C LIGNIN 5-Amino-4-imidazole 4.3.2.2 5-Aminoimidazole (N-succinylcarboxamide)-R P carboxamide-R P (AMP) Carbamoyl ß-alanine HN OC OH THYROXINE 6.3.2.6 O C CH3CH 2OH 2.3.1.41 3-OH-Hexanoyl-ACP 4.2.1.58 3.5.1.6 Coumarate I OOC-CH-CH 2COO HNCO C N RP .7.6 3.5.2.2 CH=CHCOO (UTP) 2.6.1.22 2.6.1.52 3-Oxo-Decanoyl-ACP 1.1.1.100 2.7.4.3 2.7.4.4 Cinnamate Menaquinone 1.14.13.11 OH 1.1.1.204 1.1.3.22 Hypoxanthine 1.1.3.22 Xanthine RNA H P OCH2COCOO 3-Oxoacyl-ACP NH NH2 N C C CH C HC N RP(P) N H2NCONHCH 2CH 2COO Carbamoyl aspartate HOCH2CH(O P)COO 2.3.1.41 CH3(CH2)2CH(OH)CH 2COSACP 4.2.1.59 13 I A M I N O 1.3.1.13 CH=CHCOO OH Tyramine I N ADP HN OC 5 4.2.1.51 A R O M A T I C Phenylpyruvate O CH N HN HN 1. -OOC NH2 CH2 OC CH-COO N 1.1.1.29 2-P-Glycerate 2.7.7.6 ß-Ureido isobutyrate 1. ACETATE Mitochondrial 3-OH-Decanoyl-ACP CH3CH=CHCO.S-ACP CH3CH2CH2COSACP ACYL-CoA D E G R A D A T I O N 3-OH-Acyl-ACP 2. ß-Alanine HOCH2CH(OH) COO 5.4.2.1 3.5.1.6 CH 3COO CH 3(CH2)n COCH 2COSACP 1.1.1.100 60 CH3(CH2)6CH(OH)CH 2COSACP 1.1.1.100 CH3(CH2)6CH=CHCOSACP 2, 3-Decenoyl-ACP 1.3.1.9 POCH2CH(OP) COO 2, 3-Diphosphoglycerate NH I MELANIN 2.7 H2NCONHCH 2CHCOO H2NCH 2CH2COO HC Endoplasmic Reticulum Chain elongation 3, 4-Decenoyl-ACP 1.3.1. Thromboxane B2 CH3(CH2)14COCH 2COS-CoA CH 3(CH2)n CH(OH)CH 2COSACP 4.2.1.60 4.2.1.61 CH3(CH2)5CH=CHCH 2COSACP Decanoyl-ACP OH 4.1.1.11 Phosphoserine 2.7.1.31 Oxostearoyl-CoA CH3(CH2)14COCH 2COS-CoA CH 3(CH2)14COSCoA CH3(CH2)6CH2CH 2COSACP 5.3.99.5 Prostaglandin PGE 2 Palmitoyl-CoA ACYL-ACP OH O HO O O N C CH C OC NH NH CO DNA .7 CH3 3-Aminoisobutyrate 4.2.1.22 + P OCH2CH(NH3)COO 1.1.1.95 3-P-Glycerate COO OH-Stearoyl-CoA CH3(CH2)n CH=CHCOS-CoA 1.3.1.9 2, 1.3.1.10 COO COS-CoA CH3(CH2)14CH(OH)CH 2COS CH3(CH2)14CH=CHCOS-CoA Dehydrostearoyl-CoA Palmitoyl-ACP O HO Palmitoleoyl-ACP COSCoA Stearoyl-CoA B I O S Y N T H E S I S 5. 1.1 3.99 4.9 .3 9.1 CO-S-ACP POCH2CHOH COO OH N H CH2CH2NH2 .1.2 O 1.17.4.1 20 3.1.3.3 Hydroxypyruvate ATP COO Leukotriene B4 + SERINE HOCH2COCOO ADP C C URATE 2.7.4.6 ATP 4.2.1. CH3 H2NCH 2 CHCOO HOCH2CH(NH3)COO P-Ribosyl-PP HO COO 4.6.1.1 ATP 4.1.2.5 CHOLINE 1:3-bis-P-Glycerate OP O P FOLIC ACID C1 POOL + HOCH2CH2N (CH3) 3 2.7.2.3 Arachidonate 1.13.11.34 Allantoin 2.7.7 Betaine aldehyde OH OH 1.7.3.3 NH d-ATP 2.1.2.1 2.6.1.51 1.4.1.7 OC 2.7.4.6 OHCCH 2N(CH3)3 1.2.1.12 C HN d-ADP 1.1.99.1 1.2.1.13 3.6.1.34 γ-Linolenate OH Cyclic AMP + 2.4.2.14 O OH OH O 1.4.4.2 1.2.1.8 6.3.4.7 Pi NAD+ H2 N RP NH2 N N CH O O HC O N N -O P~O P~O P O CH 2 O O O O CH N N CH2 O O 2NHCH3 Betaine Pi CH2OP O ATP N C N H NH H 2.1.1.5 .1 5.3.1 2.7.1.28 2.7.6.1 NH2 Dimethylglycine NADH Fixation β2 ATP 3.5.2.5 + Glyceraldehyde CO2 1 εε c ATP .1 5.3.1 (Glycerone-P) Ribulose-1,5-bis-P NH HC P 1.5.99.2 3-P-Glyceraldehyde 4.1 N C C CH N NH CO OC OC OOCCH2N(CH3)3 HOCH2COCH2OP 2.2.1.1 ADP Pi O OOCCH 2N(CH3)2 4.1.2.13 COO 1.3.1.35 Glyoxylate N O Sarcosine POCH 2CHOHCHO NADP+ ATP synthase e 1.14.99.25 2. OOCCH Sedoheptulose-PP CHLOROPLAST OUTER MEMBRANE Linoleate NH2 C N H H H2 N Allantoate + .1.4 2.6 .10 .1 20 1.4 1. 1. GLYCINE CH2OP O RP OOC N HC H 2N C CHO NH CH2COCOO PHENYLALANINE Ubiquinone O Prephenate 2.6.1.5 4.3.1. 5 1.3.1.13 HN CH 2COCOO + + 1.14.18.1 Plastoquinone NH2 CO COO OC CH2(NH3)COOH CO CH2OP Fructose1:6-bis-P 2.2.1.2 H 2N 3.5.3.4 2.2.1.1 H+ STROMA H C Dopaquinone NH H 2C HN C RP Urea OH OH OH H D-Ribose-5-P H+ THYLAKOID MEMBRANE H O OCH 3 1.14.16.1 2-Amino muconate OH 5.4.99.5 Chorismate CH2CH(NH3) COO H2 C CH-COO + NH3 O (Vitamin E) OOC 4.1.3.27 NH 2 OOC OOC Anthranilate CH2CH(NH3) COO Dopa 1.14.18.1 α-Tocopherol 1.14.12.1 NH2 2.4.2.18 OC-COO OH 4.6.1.4 + TYROSINE 1.2.1.32 COO CH2 O-C-COO Shikimate-5 enolpyruvate 3-P 6.3.3.1 5-Amino 4.1.1.21 5-Amino-4-imidazole Formyl 6.3.5.3 Formyl carboxylate-R P imidazole-R P glycinamide-R P glycinamidine-R P 6.3.4.13 ADP NH OH 4.1.1.28 Dopamine CHOHCH 2OH CHO OC H2NCONH 2 OH OH H CO CH 2OH D-Xylulose-5-P flo ADP γ H+ ATP 1.14.17.1 .1.6 NH H 2C 2.1.2.2 2.7.1.11 3.1.3.11 Erythrose-4-P NHCOCH 2NH2 OH OH Glycinamideribosyl-P CH CH2OP O CH2CH(NH3) COO 1.14.16.2 OH OH 4-OH-3-Methoxyphenylglycol CO CH2OH OH OH OH OH OH β H+ THYLAKOID LUMEN C C CHO POCH 2 C OH H 5 β H+ HO C H H POCH 2 2 H+ H OH OH C N-(5-P-Ribosyl) anthranilate + CH2CH(NH3) COO- CH2CH2NH2 OH OCH NH2 COO COO OH OH 2.6.1.5 Hydroxyphenyl pyruvate 1.3.1.13 2.1 1.4 C OH OH 4.1.1.48 P O 2.5.1.19 Shikimate-3-P PEP OH 1.13.11.27 Homogentisate (Normetadrenaline) NH COO OH OH (Noradrenaline) CHOHCH 2NH2 4-OH-3-MethoxyD-mandelate OH OH H OH OH α H+ H+ H+ PC PC H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ Protons from Water H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H POCH2 C Fructose-6-P OH OH 5.3.1.6 OH .3.4 P O CH2COCOO OH Normetepinephrine OCH 3 CH2OP O CO CH2OH 5.1.3.1 α α 1 Fe-S 2e- Cyt.f H+ O2 C NADPH+H+ a H+ C H+ H+ Translocated protons H+ H 2.2.1.1 OH OH OH H+ A1 4H+ H 2O H OH HO OH Shikimate Quinolinate COO H 2.7.1.71 COO N N-Acetyl-5-O-methyl-serotonin OCH NH2 COO 1-(o-Carboxy phenylamino) 1-deoxyribulose-5-P OH OH COO NH 2.1.1.4 NH2 OH COO CH2COO Norepinephrine OCH 3 OH CH(OH)COO OH NADPH 5.1.3.1 (Adrenaline) CH2 OP O OH 2.1.1.28 Epinephrine 5.3.1.9 5.3.1.8 1.1.1.44 H+ Chl.A0 2PQ NADP + NADP + CH2OP CHO 3 3 2e- ren t) 2 2 . 2PQ 2e- C C COO - .1.1 H+ Fe-S 2e- Mn C C .17 OH OH 2.7.1.2 2.7.1.1 1.1.1.25 CHOHCH 2NH2 CHOHCH 2NHCH 3 ATP Glucose-6-P P-Glucono lactone .1 3.1 Maleyl acetoacetate ADP 1.1.1.49 1.13.11.5 2.4.2.19 CH2 HO OH Dehydroshikimate OH 2.4.2.19 4.1.1.45 3-Hydroxy 1.13.11.6 2-Amino-3-carboxy 2-Aminomuconateanthranilate muconate semialdehyde 6-semialdehyde COO H H Catechol 3.7.1.3 COO HOC-CH(OH)CH(OH)CH 2OP CH N COO OH O 4.2.1.10 O CH2COO COO 5.2.1.2 COO OH OH H Quinolinatenucleotide CH 2CH2NHCOCH 3 CH3O COO NH2 3-Hydroxy kynurenine C-CH(OH)CH(OH)CH 2OP CH Indole-3-glycerol-P COO Dehydroquinate O O CH2COO Fumaryl acetoacetate GLUCOSE 2.6.1.16 OH D-Ribulose-5-P 2.7 8 1e- Cyt bf 2PQH2 C C 2.7.1.17 *2e Cyt bc _ 2e- P680 Chl.a H C POCH2 CH2OH CO Ferredoxin 2e- PQ PQH2 QA . _ Pheophytin H OH H OH O 4.6.1.3 3-Deoxy-D-arabinoheptulosonate-7-P -OOC 3.1.3.9 O HO OH .1.4 H CH2OH 5.1.3.4 8 QB CO D-Ribose OH C H 2.7 w H+ 2H+ PQH2 C Ribitol D-Xylulose PQ C CHO PHOTO- H+ otophosphoryla SYSTEM lic n-cyc electr tion l 2H+ yclic Ph No (electric cur on C 2e- H C OH H H+ H+ PHOTOSYSTEM II H C OH OH OH OH H H+ C OH OH H H C CH2OH OH N 4.2.1.20 TRYPTOPHAN HO O 5.4.2.2 NH 4.1.1.28 HOCH HCOH C H Kynurenine + CH2CH(NH 3)COO COO OC P OCH 2 CH2 CH2OH O HO OH 1.1.1. OH OH H OH 6-P-Gluconate NADPH OH OH H HOCH 2 C H Fructose-1-P CH2OH C POCH2 C H .9 C NH Tryptamine OPPU OH HO 3.2.1.48 CH2OP O 2.7.1.3 HOCH 2 C 2.7.1.47 OH OH 1.1.1 C OH OH H CH 2OH O + COCH2CH(NH 3)COO OH 1.14.13.9 + COO N RP N (MELATONIN) + CO CH2CH(NH 3)COO 1.13.11.11 CH2CH 2NH2 OH Glucose-1-P OH 21 Sorbitol CO H D-Xylose CO CH2OH HOCH 2 C 1.10.2.1 1.10.3.3 CO O L-Ribulose 2.7.1.16 L-Ribulose-5-P L-Lyxose OH H POCH2 HOCH 2 C C OH H OH OH CHO OH OH CO CO CH 2OH L-Xylulose-5-P CH 2OH Xylitol .1.4 POCH2 2.7.1.53 C OH H 5.3 H C H HOCH 2 C H 2.4.1.22 OH 3.2.1.26 SUCROSE OP OH NH 11 Nicotinatenucleotide CH2CH2NHCOCH 3 NH NH2 3.5.1.9 Formylkynurenine Indolepyruvate HO COO COO NICOTINATE 2.4.2. Ribose- P 2.7.7.18 Desamino-NAD CH 2CH2NH 2 + N (SEROTONIN) + CO CH2CH(NH 3)COO CHO NH 4.1.99.1 NH UDP-Galactose OP P Glucosamine-6-P OH OH H H HO 5.1.3.2 2.7.7.10 NH2 5.3.1.8 CH2OH CO Dehydroascorbate HOCH 2 C CH 2OH L-Xylulose OH OH H C CO OH C O C OH OH OH H C 1.1.1.14 OH H C H C 4 CH 2COCOO OH 2.7.7.12 CH 2OH O HO OH HO OH 2.3.1. 5.5.1.4 CO H OH H C OH H CHO C OH H D-Arabinose 5.3.1.3 D-Ribulose 4.1.1.34 OH OH HOCH 2 C OH C OH OH H L-Arabitol HOCH 2 H C C C HOCH2 2, 3-Dioxogulonate C C ASCORBATE CO COO - CO OH H H C H HOCH 2 C H 1.1.1.130 3-Dehydrogulonate HOCH 2 C HOCH 2 C OH OH 2.4.1.9 Fructose Inositol-P OH H H O OH H C COO- CO HOCH 2 2.7.7.9 CH 2OP O NHCOCH 3 OH OH 3.1.3.25 Inositol CO Gulonolactone 1.1.3.8 2-Oxogulonolactone 1.1.1.45 OH 2.7.7.27 2.4.1.13 N-Ac-Glucosamine-6-P HO OH OH 1.13.99.1 OH H HO OH OP HO OH OH Glucuronate CO OH OH OH 1.1.1.19 OH OH C C OH HO OH OH H OP NHCOCH 3 5.4.2.3 N-Ac-Glucosamine-1-P HO 2.7.7.24 Mannose-6-P OPPU UDP-Glucose Galactose-P 2.7.7.34 TDP-Glucose CH 2OP O HO OH HO OH CH2OP O 2.7.7.23 O GDP-Glucose HO 1.14.16.4 O O 5-Hydroxytryptamine 2.3.1.5 N-Acetyl-serotonin 4.1.1.28 5-Hydroxytryptophan Indole 4.1.1.43 CH2OH O 2.7.1.6 NH NH NH Ribose - O - P - O - P - O -Adenosine 6.3.5.1 6.3.1.5 HO COO O O N O O + CH2CH(NH3)COO HO Indoleacetaldehyde + O O Ribose -O - P - O - P - O- Adenosine(P) NAD( +P) CH2CHO GALACTOSE HO OH 1.1.1.22 5.4.2.8 CH2OH O NHAC 5.1.3.14 4.2.1.46 (Auxin) 3.2.1.23 2.7.1.38 OH OH CH2OH O OH Indoxyl 1.2.3.7 OH OH ADPGlucose NH Indoleacetate CH2OH O 2.4.1.1 2.4.1.11 HO etc. 2.4.1.21 OPPT OH OH MANNOSE 2.7.7.13 HO OH HO O P UDP-Glucuronate 4.1.3.20 HO OH N-Ac-Mannosamine Gulonate P H O T O S Y N T H E S I S CH2OH O 2.4.1.21 + N OH NH OH OH LACTOSE O TDP-4-Oxo6-deoxyglucose HO OH HO OH 5.1.3.6 OPPU OH 5.1.3.13 O CH2OH O 2.7.1.60 ACNH HO OH OH 3.1.1.18 HOCH 2 P E N T O S E S OPPU CH3 2.4.1.33 GDP-Mannose OH O 5.1.3.7 OH OH HO OH HO OPPG UDPGalacturonate COO CH2OH O 4.2.1.47 O OH UDP-N-AcGalactosamine OPPU NHAC UDP-N-AcGlucosamine pyruvate N-Ac-Mannosamine-6-P CH2OH O COO - NHCOCH 3 3.1.3.29 ACNH 4.1.3.20 HO OH OH H E X O S E S 5.1.3.12 OPPU OH OH 2.7.7.43 CH2OP O CH2OH O COO O OH 2.4.1.29 TDP-Rhamnose GDPMannuronate OH CH2OH O OH OPPT GDP-Fucose 2.4.1.16 COO HO CH3 HO OPPG HO HO O O CH3 OH UDP-N-Ac-Muramate 1.1.1.132 2.4.1.68 2.4.1.69 OPPU OH UDPIduronate COO- HO CMP-N-Acetyl neuraminate AcNH HO 2.4.1.17 CH2COO CH2OH O .5 O CHOH CHOH AcNH 2 COO CONH 2 GLYCOGEN 6. 3. 5 GLYCOPROTEINS GANGLIOSIDES MUCINS 19 1. 4. 1. P O L Y S A C C H A R I D E S HOCH HC CH2 CHCOO N 3-Hydroxypyrroline5-carboxylate 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 1.5.1.2 Creatinine Proton Flow Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme Commission (EC) Reference Numbers of Enzymes 22nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-Aldrich Cat. No. M3782 Germany SIGMA-ALDRICH CHEMIE GmbH Free Tel: 0800 51 55 000 Free Fax: 0800 64 90 000 Tel: (+49) 89 6513 0 Fax: (+49) 89 6513 1160 Greece SIGMA-ALDRICH (O.M.) LTD. 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