Metabolic Pathways bionavigate 22nd Edition

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. Tel: (+30) 210 994 8010 Fax: (+30) 210 994 3831 Hungary SIGMA-ALDRICH Kft Ingyenes telefonszám: 06 80 355 355 Ingyenes fax szám: 06 80 344 344 Tel: (+36) 1 235 9055 Fax: (+36) 1 235 9050

India SIGMA-ALDRICH CHEMICALS PRIVATE LIMITED Telephone Bangalore: (+91) 80 6621 9400 New Delhi: (+91) 11 4358 8000 Mumbai: (+91) 22 2570 2364 Hyderabad: (+91) 40 4015 5488 Kolkata: (+91) 33 4013 8003 Fax Bangalore: (+91) 80 6621 9650 New Delhi: (+91) 11 4358 8001 Mumbai: (+91) 22 2579 7589 Hyderabad: (+91) 40 4015 5466 Kolkata: (+91) 33 4013 8016

Ireland SIGMA-ALDRICH IRELAND LTD. Free Tel: 1800 200 888 Free Fax: 1800 600 222 Tel: (+353) 402 20370 Fax: (+ 353) 402 20375 Israel SIGMA-ALDRICH ISRAEL LTD. Free Tel: 1 800 70 2222 Tel: (+972) 8 948 4100 Fax: (+972) 8 948 4200 Italy SIGMA-ALDRICH S.r.l. Numero Verde: 800 827018 Tel: (+39) 02 3341 7310 Fax: (+39) 02 3801 0737

Japan SIGMA-ALDRICH JAPAN K.K. Tel: (+81) 3 5796 7300 Fax: (+81) 3 5796 7315 Korea SIGMA-ALDRICH KOREA Free Tel: (+82) 80 023 7111 Free Fax: (+82) 80 023 8111 Tel: (+82) 31 329 9000 Fax: (+82) 31 329 9090 Malaysia SIGMA-ALDRICH (M) SDN. BHD Tel: (+60) 3 5635 3321 Fax: (+60) 3 5635 4116

Mexico SIGMA-ALDRICH QUÍMICA, S.A. de C.V. Free Tel: 01 800 007 5300 Free Fax: 01 800 712 9920 Tel: (+52) 722 276 1600 Fax: (+52) 722 276 1601 The Netherlands SIGMA-ALDRICH CHEMIE BV Free Tel: 0800 022 9088 Free Fax: 0800 022 9089 Tel: (+31) 78 620 5411 Fax: (+31) 78 620 5421 New Zealand SIGMA-ALDRICH NEW ZEALAND LTD. Free Tel: 0800 936 666 Free Fax: 0800 937 777 Tel: (+61) 2 9841 0555 Fax: (+61) 2 9841 0500

Norway SIGMA-ALDRICH NORWAY AS Tel: (+47) 23 17 60 00 Fax: (+47) 23 17 60 10

Singapore SIGMA-ALDRICH PTE. LTD. Tel: (+65) 6779 1200 Fax: (+65) 6779 1822

Poland SIGMA-ALDRICH Sp. z o.o. Tel: (+48) 61 829 01 00 Fax: (+48) 61 829 01 20

Slovakia SIGMA-ALDRICH spol. s r. o. Tel: (+421) 255 571 562 Fax: (+421) 255 571 564

Portugal SIGMA-ALDRICH QUÍMICA, S.A. Free Tel: 800 202 180 Free Fax: 800 202 178 Tel: (+351) 21 924 2555 Fax: (+351) 21 924 2610

South Africa SIGMA-ALDRICH (PTY) LTD. Free Tel: 0800 1100 75 Free Fax: 0800 1100 79 Tel: (+27) 11 979 1188 Fax: (+27) 11 979 1119

Russia SIGMA-ALDRICH RUS, LLC Tel: (+7) 495 621 5579 Fax: (+7) 495 621 5923

Spain SIGMA-ALDRICH QUÍMICA, S.A. Free Tel: 900 101 376 Free Fax: 900 102 028 Tel: (+34) 91 661 99 77 Fax: (+34) 91 661 96 42

United Kingdom SIGMA-ALDRICH COMPANY LTD. Free Tel: 0800 717 181 Free Fax: 0800 378 785 Tel: (+44) 1747 833 000 Fax: (+44) 1747 833 313

Sweden SIGMA-ALDRICH SWEDEN AB Tel: (+46) 8 742 4200 Fax: (+46) 8 742 4243

United States SIGMA-ALDRICH Toll-Free: 800 325 3010 Toll-Free Fax: 800 325 5052 Tel: (+1) 314 771 5765 Fax: (+1) 314 771 5757

Switzerland SIGMA-ALDRICH CHEMIE GmbH Free Tel: 0800 80 00 80 Free Fax: 0800 80 00 81 Tel: (+41) 81 755 2828 Fax: (+41) 81 755 2815

Vietnam SIGMA-ALDRICH PTE LTD. VN R.O. Tel: (+84) 3516 2810 Fax: (+84) 6258 4238 Internet sigma-aldrich.com