Metabolic Pathways

P O L Y S A C C H A R I D E S
GLYCOPROTEINS GANGLIOSIDES MUCINS
AcNH CHOH CHOH

BLOOD GROUP ALGINATES O-ANTIGENS HYALURONIC ACID DERMATAN STARCH SUBSTANCES PEPTIDOCHITIN CHONDROITIN PECTIN INULIN CELLULOSE GLYCAN CH OH
2

CONH 2

COO O O

GLYCOGEN
CH2OH O HO O OH OH OH OH OH CH2OH O NH

CH2COO

OH NH

O
+ N

COO

Ribose -O - P - O - P - O- Adenosine(P)
O O

Ribose - O - P - O - P - O -Adenosine
O O

NICOTINATE
11 2.4.2.
2.4.2.19
CH 2CH2NHCOCH 3 NH

COO

COO
+ COO N RP

O COO -

O OPPU NHAC

CH2OH
HO

2.4.99.7
OPC

6.3.2.7-10 6.3.2.13 HO O
CH3CH COO-

O COO -

2.4.1.68 2.4.1.69
OPPU CH3 HO

1.1.1.132
O HO OPPG OH

HO CH3

O OPPT

Indoleacetate
(Auxin)
1.2.3.7
CH2CHO NH

Indoxyl
HO NH

NAD( +P)
NH

6.3.5.1 6.3.1.5
HO NH CH 2CH2NH 2

Desamino-NAD
HO

2.7.7.18

Ribose- P

Nicotinatenucleotide
CH3O

Quinolinatenucleotide
2.4.2.19
COO

2.4.1.17

HO

OH

UDP-N-Ac-Muramate
HO CH2OH O COO OH OH 2.7.7.43 OPPU NHCOCH 3

UDPIduronate
5.1.3.12
COO O HO OH

OH

OH OH

2.4.1.29 2.4.1.21 2.4.1.1 2.4.1.11 HO etc. 2.4.1.21

LACTOSE
CH2OH O OH OH

+ CH2CH(NH3)COO

CH2CH2NHCOCH 3

CMP-N-Acetyl neuraminate
AcNH O CHOH CHOH CH2OH COO

GDP-Fucose
CH2OH O

GDPMannuronate

TDP-Rhamnose
CH3 O OPPT OH

OH

3.2.1.23 2.7.1.38

5.1.3.13 O 2.4.1.33
CH2OH O HO OH HO OH OH

Indoleacetaldehyde
4.1.1.43
CH 2COCOO NH

Indole
1.14.16.4

5-Hydroxytryptophan
+ CO CH2CH(NH 3)COO CHO

4.1.1.28

5-Hydroxytryptamine 2.3.1.5 N-Acetyl-serotonin

(SEROTONIN)
+ COCH2CH(NH 3)COO OH NH2

NH

2.1.1.4

COO

N-Acetyl-5-O-methyl-serotonin
(MELATONIN)
COO OCH NH2 COO

Quinolinate

4.2.1.47

2.4.1.16 1.1.1.158
CH2OH O

HO OH HO OPPG

3.1.3.29
HO

GDP-Mannose
OPPU OH CH2OH O

TDP-4-Oxo6-deoxyglucose
4.2.1.46

ADPGlucose

CH2OH O OH HO OH

GALACTOSE
2.7.1.6
OPPU HO CH2OH O OH OP OH

+ CO CH2CH(NH 3)COO NH2

COO OH NH2

4.1.99.1

NH

Indolepyruvate
2.4.1.22

Formylkynurenine
1.13.11.11
+ CH2CH(NH 3)COO NH

3.5.1.9

N-Ac-Neuraminate
(Sialate)
CH2OP O

HO O CH2 C COO

OPPU NHAC

UDP-N-AcGalactosamine
COO O

Kynurenine 1.14.13.9 3-Hydroxy kynurenine

C-CH(OH)CH(OH)CH 2 OP CH

3.7.1.3

UDPGalacturonate
OPPU

2.7.7.13

MANNOSE
2.7.1.7
CH 2OP O

GDP-Glucose
1.1.1.2 2
2.7.7.27 2.7.7.34

HO

UDP-Glucose Galactose-P
2.7.7.9
CH 2OH O HO OH HO HO 5.1.3.2 2.7.7.10

CH2CH 2NH2 NH

HO OH HO O P

UDP-N-Ac3.1.3.29 ACNH 4.1.3.20 Glucosamine HO OH OH pyruvate N-Ac-Mannosamine-6-P

CH2OH O CH2OH O

5.1.3.7
HO OH

Mannose-1-P
5.4.2.8

5.1.3.6

TDP-Glucose
2.7.7.24

CH 2OH O

Tryptamine
OPPU COO OC P OCH 2 CH2 HOCH HCOH C

4.1.1.28

4.2.1.20

TRYPTOPHAN
HO COO COO OH OH OH

Indole-3-glycerol-P
COO HO OH OH

COO HOC-CH(OH)CH(OH)CH 2OP CH N

4.1.1.45 3-Hydroxy 1.13.11.6 2-Amino-3-carboxy 2-Aminomuconateanthranilate muconate semialdehyde 6-semialdehyde COO H H Catechol
NH C C CH CH2OP COO NH2

OCH NH2 COO

A R O M A T I C A M I N O A C I D S

9 .1 .1 1.4

1.2.1.32 1.14.12.1
OOC OOC NH 2

OH OH

OH

2.7.7.12

UDP-Glucuronate
CH2OH O HO OH CH2OP O OP NHCOCH 3 5.4.2.3 HO OH

OH

1-(o-Carboxy phenylamino) 1-deoxyribulose-5-P

COO

4.1.1.48

N-(5-P-Ribosyl) anthranilate
COO CH2

2.4.2.18

Anthranilate
OOC

HO OH HO OH

OH

COO

4.1.3.20
OPPU

CH2 OH OC-COO

4.1.3.27
OH

CH 2COCOO

2-Amino muconate

H E X O S E S

ACNH HO OH OH

2.7.1.60
HO OH NHAC OH

Mannose-6-P
2.4.1.9

2.4.1.13

CH 2OP O HO OH OH NH2

OP

UDP-Galactose
CH2OH O -OOC HO OH
OH

OH

N-Ac-Mannosamine

5.1.3.14

UDP-N-Ac-Glucosamine
COO O OH

N-Ac-Glucosamine-1-P
2.7.7.23
OH OH OH OH OP HO OH
OH

N-Ac-Glucosamine-6-P
H H C OH C CO CH2OH C

NHCOCH 3

Glucose-1-P

3-Deoxy-D-arabinoheptulosonate-7-P
O O CH2COO

4.6.1.3
O

OH

P O

Dehydroquinate

4.2.1.10

Dehydroshikimate
CH2COO

1.1.1.25

Shikimate

2.7.1.71

OH

OH

P O

OH

CH2COCOO

Shikimate-3-P PEP

2.5.1.19

Shikimate-5 4.6.1.4 enolpyruvate 3-P

+

OH

O-C-COO

Chorismate
+

5.4.99.5

Prephenate
CH2COCOO

CH2CH(NH3) COO

CH2CH(NH3) COO

2.3.1.4
5.3.1.8

Glucosamine-6-P
3.2.1.26 3.2.1.48

OH H HOCH 2 C H C

OH OH C C H COO HO OH OH OH HO OH

HOCH 2

OH

OH OH H OH

OH H OH H

Fructose
1.1.1.14
H H C OH H C C CH2OH OH

SUCROSE
5.5.1.4

GLUCOSE
5.4.2.2 3.1.3.9

Fumaryl 5.2.1.2 Maleyl 1.13.11.5 Homogentisate acetoacetate acetoacetate

CHOHCH 2NHCH 3 OH OH CHOHCH 2NH2 OH

COO

O CH2COO
OH

4.2.1.51 1.3.1.13

1.13.11.27

OH

1.3.1.13

Hydroxyphenyl pyruvate

2.6.1.5
+

OH

TYROSINE

1.14.16.1

PHENYLALANINE
1.3.1.13

2.6.1.5 4.3.1. 5

Phenylpyruvate

Gulonate
3.1.1.18 HOCH 2
C H C C H O

1.1.1.19
OH OH C H CO

Glucuronate
OH H HOCH 2 C H C OH C H O

1.13.99.1

Inositol
HOCH 2 C H

3.1.3.25
OH H

CH2CH2NH2 OH

CH2CH(NH3) COOOH

Inositol-P
C CO

4.1.

1.25
+

CH2CH2NH2

CH=CHCOO

OH OH C O
HOCH 2 C CH2OP O

CO

CO

1 1.1.1.2
2.6.1.16
O

ATP
2.7.1.2 2.7.1.1

OH

Epinephrine
(Adrenaline)

2.1.1.28

Norepinephrine
(Noradrenaline)
2.1. 1.6

1.14.17.1

OH

Dopamine -Tocopherol
(Vitamin E)

4.1.1.28 1.14.18.1
O

OH

1.14.16.2

Ubiquinone
CH2CH(NH3) COO
OH

Dopa
HN
H2 C CH-COO + NH3

Cinnamate Menaquinone
1.14.13.11
CH=CHCOO

Tyramine

Gulonolactone 1.1.3.8 2-Oxogulonolactone

1.1.1.45
OH H HOCH 2 C C OH CO OH C COOH OH H HOCH 2 C H C OH CO CO COO H

ASCORBATE
OH H HOCH2 C H C CO O

1.10.2.1 1.10.3.3
CO

OH OH H

Sorbitol
2.7.1.3
H H C OH H C C COO -

2.7

ADP
CH2 OP O

CHOHCH 2NH2 OCH 3 OH

O O

.1.4

HO OH OH

I O

1.1.1.49

Coumarate
OH

CO

P E N T O S E S

3-Dehydrogulonate
OH H HOCH 2 C H C OH C CHO

1.1.1.130
H

2, 3-Dioxogulonate
H C OH C CHO H HOCH 2 C H C

Dehydroascorbate
POCH2
CO CH 2OH H H C OH C CO

3.1.

1.17

P-Glucono lactone
NADP +
5.3.1.8

Glucose-6-P
HO OH OH OH

CH(OH)COO OCH 3 OH

Normetepinephrine 4-OH-3-MethoxyD-mandelate
3.4 1.4.

CHOHCH 2OH OCH 3 OH

O I O
NH OH

(Normetadrenaline)

Dopaquinone Plastoquinone

HOCH 2

OH H

OH OH H

OH OH

OH OH H OH 6-P-Gluconate NADPH CH2OP

5.3.1.9

4-OH-3-Methoxyphenylglycol
NH H 2C OC CHO NH RP H 2C NH

1.14.18.1

MELANIN

THYROXINE
OOC-CH-CH 2COO HNCO C N

LIGNIN

Tannins

Plant Pigments

L-Xylose
OH H HOCH 2 C H C H C OH OH

4.1.1.34

D-Arabinose
OH H HOCH 2 C H H C OH OH H C C OH CO

5.3.1.3

D-Ribulose
OH H

2.7.1.47

HOCH 2 C

NADP +

OH OH H

Fructose-1-P
CO CH2OH HOCH 2
H H H

1.1.1.44

H C

HO C CO CH2OH

CH2OP O

NHCOCH 2NH2

2.2.1.1 5.1.3.1

POCH2 C

CH2OH

CH 2OH

POCH2

C H H

C OH

NADPH

OH OH H

HN C

CHO NH

H 2N
RP

HC C

N CH N

OOC C C

N CH N RP

O C CH

N C C N CH RP O C C C NH N CH N RP

L-Arabitol
OH OH H HOCH 2 C H C H C OH CHO

L-Xylulose
HOCH 2 C

2.7.1.53

L-Xylulose-5-P
OH H C OH HOCH 2 C C OH H

CH2OH

H C CO CH2OH H H C CHO

Fructose-6-P ATP
3.1.3.11 2.7.1.11

OH OH

OH OH OH

CH 2OH

CHO

Ribitol
H HOCH 2 C H C H C CHO

POCH2

Glycinamideribosyl-P
6.3.4.13

2.1.2.2

6.3.5.3 6.3.3.1 Formyl Formyl 5-Amino 4.1.1.21 5-Amino-4-imidazole carboxylate-R P glycinamide-R P glycinamidine-R P imidazole-R P
H2NCONH 2

RP

H2 N

H 2N

H 2N H 2N

6.3.2.6

5-Amino-4-imidazole 4.3.2.2 5-Aminoimidazole (N-succinylcarboxamide)-R P carboxamide-R P

HN HC O C N

RP

C A T E C H O L A M I N E S

OH OH

1.1.1.10

OH H

L-Arabinose
OH H HOCH 2 C H C H C OH OH

5.3

.1.4
HOCH 2

Xylitol
OH OH C H C H

2.7.1.47

D-Ribulose-5-P
5.1.3.1
H OH C CO CH 2OH OH OH OH

POCH 2 C

D-Xylose
OH OH

Erythrose-4-P
H H C HO C CO CH2OP CH2OP O

OH OH

ADP
POCH 2
C

Urea
3.5.3.4
CH2(NH3)COOH
+

H 2N
OC

COO C N H H

NH2 CO
NH

H2 N
OC

CHO

CO CH2OH

POCH2 C
H

C H

CO CH OH 2

Allantoate
NH2

3.5.2.5

NH OC CO C N H NH H

HN OC

C N H

NH C C CO NH

Allantoin

1.7.3.3
NH2

URATE
N CH N
N HC

1.1.1.204 1.1.3.22 Hypoxanthine 1.1.3.22 Xanthine

NH2 N C C CH C N RP(P) N

N C CH C OC NH NH HN

O C

2.1.2.3
N C C CH NH

H2 N HCO

3.2.2.2

Inosine
2.4.2.1

3.1.3.

Formylamidoimidazolecarboxamide-R P
3.5.4.10
HN O C N N C C CH N RP

D-Ribose
5.1.3.4
5.3.1.6
POCH 2

L-Lyxose

L-Ribulose 2.7.1.16 L-Ribulose-5-P

1.1.1. 9
H HOCH 2 C OH C CO CH2OH OH H

OH OH H

2.7
2.7.1.17

4.1.2.-

.1.1

OH H

2.2.1.2

D-Xylulose-5-P

Fructose1:6-bis-P

NH2

.1.4 2.6 10 0 1. .2 1.4. .1

GLYCINE
O O P O O

N
HC

N
CH

N O HC O O N -O P~O P~O P O CH 2 O O O O

OOC-CH-CH 2COO

HC

D-Xylulose
H+
PHOTOSYSTEM II

OH OH H H C H C CHO

H+

H+

2H+ yclic Ph C 2H+

PQ PQH2 PQ
1e-

otophosphoryla SYSTEM lic n-cyc electr tion l No (electric curre on fl

PHOTO- H+

H C

H OH C C CO CH2OP

P-Ribosyl amine
4.1.2.13

Glyoxylate

Sarcosine

2.1 OOCCH 2NHCH3

N CH2 O

Fumarate

OH

1.5.99.2 1.4.4.2
OOCCH 2N(CH3)2

Cyclic AMP

4.6.1.1

ATP
d-ADP
2.7.4.6

2.7.4.6

OH OH

ADP

2.7.4.3 2.7.4.4

N HC

ADENOSINE-P
(AMP)

4.3.2.2

NH N C C CH C NH RP

Aspartate
6.3.4.4 3.1.4.6 2.4.2.1

INOSINE-P
(IMP)
O C HN N C C CH N RP

1.17.4.1 2.7.7.7

Adenylosuccinate
3.5.4.3

POCH 2 C

Adenine
2.7.7.7 2.7. 7.7 2.7.7.6

1.1.1.205 OC

OH OH OH

POCH2

Dimethylglycine
2.1.1.5
OOCCH2N(CH3)3
+

H+

H+ H+

O2

2 2

H+Protons from Water

THYLAKOID LUMEN THYLAKOID MEMBRANE STROMA

H+

H+
H+
H+
H+

3 3

H+

CHLOROPLAST OUTER MEMBRANE

COO

Linoleate
1.3.1.35

1.14.99.25
COO

-Linolenate

Arachidonate 1.13.11.34
CO-S-ACP

L I P I D B I O S Y N T H E S I S

COSCoA

Oleoyl-CoA
1.14.99.5
COSCoA

Palmitoleoyl-ACP
CH3(CH2)14CH=CHCOS-CoA

Stearoyl-CoA
CH3(CH2)14COS-ACP

Dehydrostearoyl-CoA
CH 3(CH2)14COSCoA

Palmitoyl-ACP ACYL-ACP
CH3(CH2)6CH2CH 2COSACP

Palmitoyl-CoA
1.3.1.9 2, 1.3.1.10
CH3(CH2)n CH=CHCOS-CoA

3-Enoyl-ACP

4.2.1.60 4.2.1.61

CH3(CH2)5CH=CHCH 2COSACP

Decanoyl-ACP
CH 3(CH2)2CH 2CH2COSACP

1.3.1.

3, 4-Decenoyl-ACP
9
CH3(CH2)6CH=CHCOSACP

4.2.1.6

2, 3-Decenoyl-ACP Hexanoyl-ACP
CH3CH2CH2COSACP

4.2.1.

1.3.1.9

CH3(CH2)2CH=CHCO-S-ACP

2, 3-Hexenoyl-ACP
CH3CH=CHCO-S-ACP

4.2.1.59

CH3CH=CHCO.S-ACP

Butanoyl-ACP

1.3.1.9

Crotonoyl-ACP
R-CH2COO

4.2.1.58

CH3(CH2)n+2COS-CoA

ACYL-CoA
(Cytosol)
2.3.1.7

6.2.1.3

3.1.2.20

FATTY ACID

L I P I D D E G R A D A T I O N

Carnitine O-Acyl-carnitine
O-Acyl-carnitine
3.1.1.28
CH3(CH2)n CH2CH2COSCoA

3.1.1.3

CH2O-CO-R CH2O-CO-R"

R-CO-OCH

CH2O-CO-R R-CO-OCH CH2OH

Triacylglycerol

FAT

Diacyl 2.3.1.20 glycerol

3.1.3.4 2.7.1.107

ACYL-CoA
(Mitochondria)
CH3(CH2)2CH2CH2COSCoA

1.3.99.3 1.3.99.3 1.3.99.2

CH3(CH2)n CH=CHCOSCoA

2, 3-Enoyl-CoA 2, 3-Hexenoyl-CoA Crotonoyl-CoA Pentenoyl-CoA

CH 2O-CO-R CH3CH2CH=CHCOSCoA CH3CH=CHCOSCoA CH3(CH2)2CH=CHCOSCoA

4.2.1.17 4.2.1.17

CH3(CH n CH(OH)CH 2COSCoA

Hexanoyl-CoA
CH3CH2CH2COSCoA

3-OH-Hexanoyl-CoA
CH3CH(OH)CH 2COSCoA

CH3(CH2)2CH(OH)CH 2COSCoA

Butanoyl-CoA
Odd C Fatty acids

4.2.1.55

3-OH-Butanoyl-CoA
CH3CH2CH(OH)CH 2COSCoA

Pentanoyl-CoA
CH2 O-CO-R R'-CO-OCH O CH2O-PO O

CH 3CH2CH 2CH2COSCoA

3-OH-Pentanoyl-CoA
CH 2O-CO-R R'-CO-OCH O O

OH

OH

R'-CO-OCH

1.3.99.7
HO OH OH

COO O + CH 2O PO CH 2CHNH 3 O

Phosphatidyl inositol

PHOSPHATIDYL SERINE
CH2O-CO-R R'-CO-OCH O

2.7.8.8 2.7.8.11
CH 2O-CO-R

Serine

Inositol
R'-CO-OCH

P H O S P H O L I P I D S

CH 2O-CO-R R'-CO-OCH

4.1.1.65

O HCO-CO-R

OPhosphatidyl ethanolamine CEPHALIN

O + CH 2O P OCH 2CH2 NH 3

CH2 O-POCH 2CH(OH)CH 2 O-P-OCH 2 O O

Cardiolipin

OPhosphatidylglycerol

2.7.8.1

CDP-Ethanolamine
CH2O-CO-R

+ CPP- OCH 2CH2 NH3

2.7.7.14

Ethanolamine-P
CH2OH HOCH O + CH2OPO CH2CH 2N(CH 3)

CH2OCH=CHR R-CO-OCH O

2.1.1.17 2.1.1.71

OCholine plasmalogen 1.3.1.35 Serine + NH

+ CH2OPO CH2CH2N(CH 3)3

HOCH O + CH2OPO CH2CH2N(CH 3)3 O CH 2 O-CO-R 3.1.1.32 O R'-CO-OCH + CH2OPOCH2CH2N(CH 3)3 O

- Lysolecithin

3.1.1.5

OGlycerophosphocholine

LECITHIN

+ CPP-O CH2CH2N(CH 3)3

2.7.8.2

CDP-choline
3

2.3.1.50

Dehydrosphinganin Gangliosides

CH 3(CH2)14COCHCH 2OH

+ NH 3 CH3(CH2)14CH(OH)CHCH 2OH

2.7.8.

+ NH 3 CH3(CH2)12CH=CHCH(OH)CHCH 2OH

3.1.4.12

1.1.1.102

Sphinganin

4-Sphingenin
2.4.1.23 3.5.1.23
NHCOR

2.4.1.62

UDP-Sugars Acyl-CoA

NHAcyl O + CH3(CH2)12CH=CHCH(OH)CHCH 2 O PO CH2CH2N(CH 3)3 O

SPHINGOMYELIN

2.7.8.3

CH3(CH2)12CH=CHCH(OH)CHCH 2OH

3.1.4.12

Ceramide

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

-CAROTENE (C40) Metarhodopsin

1.13.11.21
COO-

hv Rhodopsin
CH3O CH3O O CH3 n O

Opsin
CHO

Retinoate
1.2.1.36

Ubiquinone
(Coenzyme Q)

trans-Retinal
1.1.1.105

5.2.1.3

Light

11-cis-Retinal
1.1.1.105

CHO

Menaquinone Plastoquinone
O HO
CH 3 O

Retinol esters
2.3.1.76 3.1.1.21

CH2OH

CH 3
O CH3

(C15)
2.5.1.21

(Vitamin A)

Dark

(Vitamin K)

(Vitamin E)

STEROIDS Progesterone
HO

2H+ CuB Heme a3

2eH HO H H HO
1.9.3.1

F6

N2

6.3

trans-Retinol

.5

5.2.1.7

.5

CH2OH

11-cis-Retinol

Phylloquinone

-Tocopherol

Heme a

2H+

Pregnenolone

CHOLESTEROL

Desmosterol
COOCH2

HEMOGLOBIN
CH2 CH H3 C N HC N H3 C CH2 CH2 COOC H Fe N CH3 CH2 CH2 COOH3C H C N CH CH3 CH CH

CHLOROPHYLL
CH2 CH H3 C N H
H2 C

H2 C N H H N C H2

CH3 CH 2 CH CH2 CH3 CH2 CH2 COOH3 C

H2 C

CH2 N H H N H3C CH2 CH2 COO-

H2 C N H H N C H2

H N

CH2 CH2 COO-

CH2 CH2 COO-

HEME

1.3.3.4 4.99.1.1

Protoporphyrinogen

1.3.3.3

Coproporphyrinogen

2003 International Union of Biochemistry and Molecular Biology

www.iubmb.org
Argentina SIGMA-ALDRICH DE ARGENTINA, S.A. Tel: 54 11 4556 1472 Fax: 54 11 4552 1698 Australia SIGMA-ALDRICH PTY., LIMITED Free Tel: 1800 800 097 Free Fax: 1800 800 096 Tel: 612 9841 0555 Fax: 612 9841 0500 Austria SIGMA-ALDRICH HANDELS GmbH Tel: 43 1 605 81 10 Fax: 43 1 605 81 20 Belgium SIGMA-ALDRICH NV/SA. Free Tel: 0800-14747 Free Fax: 0800-14745 Tel: 03 899 13 01 Fax: 03 899 13 11
XXX

Brazil SIGMA-ALDRICH BRASIL LTDA. Tel: 55 11 3732-3100 Fax: 55 11 3733-5151 Canada SIGMA-ALDRICH CANADA LTD. Free Tel: 800-565-1400 Free Fax: 800-265-3858 Tel: 905-829-9500 Fax: 905-829-9292 China SIGMA-ALDRICH CHINA INC. Tel: 86-21-6386 2766 Fax: 86-21-6386 3966 Czech Republic SIGMA-ALDRICH s.r.o. Tel: 246 003 200 Fax: 246 003 291 Denmark SIGMA-ALDRICH DENMARK A/S Tel: 43 56 59 10 Fax: 43 56 59 05

Finland SIGMA-ALDRICH FINLAND Tel: 358-9-350-92 50 Fax: 358-9-350-92 555 France SIGMA-ALDRICH CHIMIE S..r.l. Tel appel gratuit: 0800 211 408 Fax appel gratuit: 0800 031 052 Germany SIGMA-ALDRICH CHEMIE GmbH Free Tel: 0800-51 55 000 Free Fax: 0800-649 00 00 Greece SIGMA-ALDRICH (O.M.) LTD Tel: 30 210 9948010 Fax: 30 210 9943831 Hungary SIGMA-ALDRICH Kft Tel: 06-1-235-9054 Fax: 06-1-269-6470 Ingyenes zld telefon: 06-80-355-355 Ingyenes zld fax: 06-80-344-344

H2 O

Translocated protons

P H O T O S Y N T H E S I S

Ferredoxin

2eQB QA
Pheophytin P680 Chl.a Mn
2e-

2e-

* 2eFe-S

H+

nt)

D-Ribose-5-P

OH OH OH H

Sedoheptulose-PP
2.2.1.1
POCH 2CHOHCHO

2.7.

7.7

DNA RNA
O C

d-GTP d-CTP GTP TTP 2.7.

2.7. 7.6

2.4.2.15

XANTHOSINE-P
(XMP)
2.4.2. 1
6.3.4.1 6.3.5.2
O C N C C N CH N RP HN H2 N C

d-GDP

P U R I N E S

H+

d-ATP
2.1.2.1

1.17
2.7.4.6

.4.1

Guanine GDP

Betaine
1.2.1.8
+

1e-

PQ

PQH2

Cyt bf
2e-

H+
H+ H+

NADP+

A1 Chl.A0

2PQH2

2PQ
2e-

._

Cyt bc
2e-

2PQ
PC PC PC

NADPH+H+
Pi

Dihydroxyacetone-P
(Glycerone-P)

HOCH2COCH2OP 2.2.1.1

3-P-Glyceraldehyde
1.1 5.3. 1.1 5.3. 2.7.1.28

Pi

6.3.4.7 Pi NAD+

2.4.2.14

OHCCH 2N(CH3)3

Betaine aldehyde
1.1.99.1

FOLIC ACID C1 POOL

4.1.2.5

ATP
4.2.1.2 0

2.7.7.6

2.7.4.8

2.7.

7.6
O C

4.6

1.17.4 .1

GUANOSINE-P
(GMP)
O C

P700

Fe-S 2e- Cyt.f

H+
a

H+ H+

ADP
2

H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+

4H+

H+

Pi
1

Ribulose-1,5-bis-P

Glyceraldehyde
1.2.1.13
CH2OP O

1.2.1.12

+ HOCH2CH2N (CH3) 3

CH3 H2NCH 2 CHCOO

CH3 H2NCONHCH 2CHCOO

HN OC

CH-CH3 CH 2 NH

TDP
2.4.2.4
O C

HN OC

CHOLINE
2.6.1.51 1.4.1.7
HOCH2COCOO

ADP

ATP
2

3

Fixation

CO2

NADH
POCH 2CHOHCOO P
OP O P OH OH

HOCH2CH(NH3)COO

3-Aminoisobutyrate

3.5.1.6

SERINE

4.2.1.22 4.1.1.11
H2NCH 2CH2COO

2.1

-Ureido isobutyrate
.1.1 3
3.5.1.6

3.5.2.2

Dihydro thymine
3.5.2.2

C CH3 CH NH O C

2.7.

4.9

HN OC

C N

C-CH3 CH 2.1.1.45 DP

HN OC

1.3.1.2

Thymine
CH2 CH2

THYMIDINE-P
2.4. 2.4

d-UMP

CH CH N DP 3.5.4.12 NH 2 C CH N CH OC NH O C CH CH N RPPP

NH2 C CH CH OC N DP
N

d-CMP

2.7.4.14

d-CDP

HN
H2NCONHCH 2CH 2COO OC

2.7.6.1

1:3-bis-P-Glycerate
ADP
2.7.2.3

-Alanine
3.1.3.3
-OOC NH2 CH2 OC CH-COO N

Carbamoyl -alanine
O C HN OC NH

Dihydrouracil
O C HN OC

NH

HN OC

1.3.1.2

CH CH N H
O C CH HN OC N CH RP

1.17.4.1

Uracil
O C

3.5.4.1
HN OC

Cytosine
N OC

NH 2

CDP

ATP
3.6.1.34

ATP
HO HO COO

P-Ribosyl-PP ADP

Hydroxypyruvate

CH2 CH-COO

+ P OCH2CH(NH3)COO

CH C-COO NH

HN OC

CH

C-COO N RP

2.4.2.9

CH 2.7.4.6 CH RPPP

Phosphoserine
1.1.1.29 2.6.1.52 1.1.1.95
P OCH2COCOO

Carbamoyl aspartate
2.6.1.22
H H C H C H C

3.5.2.3

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
(UTP)
H H C H C H C NH2 N OC C NH CH C HC N N H H C CO CH2 CONH 2 N NH C CH C HC N N RP

6.3.4.2

CYTIDINEtriphosphate
(CTP)
H H C C C H CH N

P Y R I M I D I N E S

COO

ATP
OH COO HO O OH

5.3 1.1 .99 4.9 .3 9.1

Leukotriene B4
COO

POCH2CHOH COO

P OCH2 C

3-P-Glycerate
2.7.1.31

P-Hydroxypyruvate
2.4.2.17
HC N

OH OH O

P-Ribosyl-ATP
C CH 2CHCOO NH C H

3.6.1.31

NH2 N + C C N CH C HC N N RP(PP)

P OCH 2

P OCH 2 C

P-Ribosyl-AMP
C NH CH + CH2CH(NH 3)COO

3.5.4.19

OH OH O

OH OH

P OCH 2 C

RP

OH OH HN

Prostaglandin PGE 2
CH3(CH2)14CH(OH)CH 2COS COS-CoA

HO

OH

5.3.99.5

Thromboxane B2
CH3(CH2)14COCH 2COS-CoA

OH-Stearoyl-CoA
CH3(CH2)14COCH 2COS-CoA

Oxostearoyl-CoA
Mitochondrial
CH 3(CH2)n COCH 2COSACP

2, 3-Diphosphoglycerate

POCH2CH(OP) COO

5.4.2.1

HOCH2CH(OH) COO

Glycerate

NHCOCH 2CH2NH2

HC N

HC N

C NH CH

P-Ribulosylformimino P-Ribosylformimino 5-aminoimidazole- 5.3.1.16 5-aminoimidazolecarboxamide-R P carboxamide-R P + +

+ CH2CH(NH 3)CHO HC N C CH 2CH(NH 3)CH2OH HC N C

Imidazole glycerol-P
HC N C H C NH CH2COCH 2OP

Carnosine
4.1.1.22

CH2CH(NH 3)CH2OP

4.2.1.19

CH 3COO

Endoplasmic Reticulum Chain elongation

CH 3(CH2)n CH(OH)CH 2COSACP HOCH2CH(O P)COO

ACETATE
HC C NH C H

HISTIDINE
4.3.1.3

1.1.1.23

Histidinal
OOC HN

1.1.1.23

Histidinol
OC N

NH CH

3.1.3.15

Histidinol-P

NH CH

2.6.1.9
CH N C

Imidazole acetol-P
CH CHCOO

2-P-Glycerate
4.2.1.11

CH2CH2NH2

1.2.1.4
CH3CH 2OH

CHCH 2CH2COO NH CH

CHCH 2CH2COO NH CH

3-OH-Acyl-ACP
CH3(CH2)6CH(OH)CH 2COSACP

1.1.1.100

3-Oxoacyl-ACP

HISTAMINE

2.3.1.41

ETHANOL
1.1.1.1

2.1.3.2

2.3.

Formimino glutamate HS HSO -

3.5.2.7

Imidazolone propionate

4.2.1.49

NH CH

4.3.1.3

Urocanate 2SO 4

3-OH-Decanoyl-ACP
CH3(CH2)2CH(OH)CH 2COSACP

1.1.1.100

CH 3(CH2)6COCH 2COSACP

1.30

3-Oxo-Decanoyl-ACP
2.3.1.41
CH2=C(OP ) COO CH3(CH2)2COCH 2COSACP

+ CH2CO-OCH2CH(NH 3)COO

60
1.1.1.100

Acetylserine
+ S-CH 2CH(NH 3)COO + S-CH 2CH(NH 3)COO

1.8.99.1

1.8.99.2

3-OH-Hexanoyl-ACP
CH3CH(OH)CH 2COS-ACP

3-Oxo-Hexanoyl-ACP
CH3COCH 2COSACP

P-enolpyruvate
ADP Malonyl-ACP
2.3.1.39
HOOCCH 2CO-S-ACP

Acetaldehyde HS
1.1 4.1.

CH3CHO

Phosphoadenylylsulphate
(PAPS)
4.2.1.22 4.4.1.8

2.7.1.25

Adenylylsulphate
(APS)

2.7.7.4

4.2.

99 + .8 HSCH 2CH(NH 3)COO

2.3.1.41

4.4.1.1

CYSTINE
4.4.1.15

1.6.4.1

CYSTEINE

+ CH2CH(NH 3)COO + SCH 2CH2CH(NH 3)COO

+ HSCH 2CH2CH(NH 3)COO

+ CH 3 SCH CH CH(NH )COO 2 2 3

4.2.99.9

Cystathionine

Homocysteine
3.3.1.1

2.1.1.13 2.1.1.14

METHIONINE
Adenosyl
+ CH 3 SCH CH CH(NH )COO 2 2 3 +

1.2.1.32

3-OH-Butanoyl-ACP
CH2OH HOCH CH2OH CH2OH HOCH CH2O P

1.1.1.100 1.1.1.8

Acetoacetyl-ACP
2.3.1.41

1.13.11.20
+ HO 2SCH 2CH(NH 3)COO + HO3SCH 2CH(NH 3)COO

Adenosyl

2.5.1.6

2.7.1.40

Glutamate
1.29
6.3. 2.2

+ SCH 2CH2CH(NH 3)COO

Glycerol
2.3.1.15

2.7.1.30

3-P-Glycerol

KETONE BODIES Acetone 3-OH-Butyrate

CH3COCH 3 CH3CH(OH)CH 2COO

3.7

.1.2

ATP

4.4.1.15

HSO3
HO2SCH 2COCOO

Cysteine sulphinate

Cysteate

4.1.

S-Adenosyl homocysteine
CH2SH + OOCCH(NH 3)CH2CH2CONHCHCOO

2.1.1.10 2.1.1.20

S-Adenosyl methionine
(SAM)

2.3.1.51
CH2O-CO-R

2.7.8.5

Malonyl-Co-A
CH 3CO-S-ACP

HOOCCH 2CO-SCoA

PYRUVATE
1.2.4.1 2.3.1.12 1.8.1.4

1.4.1.1

2.6.1.2

+ CH3CH(NH3)COO

3-Sulphinyl pyruvate
4.1.2.5
+ CH3CH(OH)CH(NH 3)COO

HO2SCH 2CH2NH2

ALANINE
4.1.3. 18
4.1.1.12

4.1.1.29

Hypotaurine

1.8.1.3

HO3SCH 2CH2NH2

Taurine

-Glutamylcysteine
6.3. 2.3

Glycine

R-CO-OCH CH2O P

4.1.1.4

1.1.1.30

Phosphatidate

Acetoacetate
3.1.2.11

CH3COCH 2COO

4.1.1.9

+ OOCCH2CH2COOCH2CH2CH(NH 3)COO

CH2SH + OOCCH(NH 3)CH2CH2CONHCHCONHCH 2 COO

Acetyl-ACP
2.3.1.38
CH3COCOO-

Succinylhomoserine
2.3.1.46
CH3

1.1. 1.

27
CH3CH(OH)COO

2.6.1.18

+ POCH 2CH2CH(NH 3)COO

+ HOCH 2CH2CH(NH 3)COO

Bile Acids
HCHO
4.1.2.12
CH3 + CHCH(NH 3)COO CH3

Glutathione
HOCH 2 C(CH 3)2COCOO

THREONINE
OHCCH 2COO-

PYRUVATE
3-OH-Acyl-CoA
1.1.1.35 1.1.1.35
CH3(CH2)n COCH 2COSCoA

LACTATE
4.2 .1 .5 2
1.2.1.18
4.1.1.32

4.1.3. 18
4.2.1.16
CH3CH2COCOO

O-Phospho- 2.7.1.39Homoserine 4.2.99.2 homoserine

COO CH3COC(OH)CH 3

Oxopantoate

1.1.1.3 1.1.1.86

CH3 C (OH)CH(OH)COO CH3

3-Oxoacyl-CoA
CH3(CH2)2COCH 2COSCoA

2.3.1.

16
6

3-Oxohexanoyl-CoA
CH3COCH 2COSCoA

2.3.1.1

NAD ATP CO2

6.4.1.1

1.2.4.1 2.3.1.12 3.1.3.43

HOH GDP CO2 GTP

Malonic semialdehyde

CHCOCOO CH3

1.1.1.169
HOCH 2 C(CH 3)2CH(OH)COO

2-Acetolactate Oxobutyrate
4.1.
CH3 HOCH 2CHCOO

2-3-Dihydroxy 4.2.1.9 2-Oxo- 1.4.1.8 VALINE isovalerate isovalerate

CH3 CH3 CH2 = CCOSCoA CH3

2.6.1.32

1.1.1.157

Acetoacetyl-CoA
CH3CH2COCH 2COSCoA

2.3.1.9

1.2.1.25

Pantoate -Alanine 3.5.1.22

6.3.2.1

NADH+H+
CH3COSCoA

1.1.1.35

3-Oxopentanoyl-CoA

4.1.3.5

NAD+
.44 2.6.1.4 2.6.1

ACETYL-CoA
1.1.1.39

CH3 OHCCHCOO

3.18
1.1.1. 31

3-Hydroxyisobutyrate
COO CH3COC(OH)CH 2CH3

3.1.2.4

3-Hydroxy- 4.2.1.17 Methyl 1.3.99.3 Isobutyryl-CoA Isobutyryl-CoA acrylyl-CoA

CH3 CH3 CHCOCOO CH3CH2 CH 3 + CHCH(NH 3)COO

HOCH 2CHCOS-CoA-

CH3CHCO-SCoA

HOCH2 C(CH3)2CH(OH)CO NHCH 2CH2COO

PANTOTHENATE
2.7.1.33
P OCH 2C(CH 3)2CH(OH)CONHCH 2CH2COO

Methylmalonyl semialdehyde
-OOCCOCH2COO-

2.7.7.41

Glyoxylate
1.1.1.79 1.2.3.5
HOCH 2COO

OHCCOO

4.1.3.5
CH2COO CH3C(OH)CH 2COSCoA

4.1.3.4

CH2O POCMP

NADH+H+
4.2.1.1 8

OXALOACETATE
NAD+
4.1.3.8

2.6.1.1 4.1.3.7 CH2COOC(OH)COOCH2COO-

2.3.1.1

CDP-diacyl glycerol
O

Glycolate
1.2.1.21 2.7.8.5
HOCH 2CHO

-OH--Methylglutaryl-CoA
1.1.1.34

4.2.1.9 2-Aceto-22-Oxo-3-methyl 2:3-Di-OHhydroxy- 1.1.1.86 3-methylvalerate valerate butyrate

CH3 CH3COCHCOSCoA CH 3 CH3CH(OH)CHCOSCoA CH3 CH3CH=CHCOSCoA

C(OH)CH(OH)COO CH3CH2

2.6.1.32

CH3CH2

ISOLEUCINE
CH 3

4-P-Pantothenate Cysteine 6.3.2.5

COO P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCHCH 2SH

1.2.1.25

4-P-Pantothenylcysteine
4.1.1.36
P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH 2SH

CH3CH 2CHCOSCoA

CH2O-CO-R

HOOC-COOH

Oxalate Glycol aldehyde

1.4.3.8
+ HOCH 2CH 2NH 3

FMN
I

I
1.1.1.37

CITRATE
4.1.3.2

CH2O-PO CH 2CHOHCH 2OH

CH2COO CH3C(OH)CH 2CHO

Glyoxylate Cycle

-OOCCHO

4.2.1.3
CH(OH)COO2COO

Propanoyl-CoA
2.1.3.1 4.1.1.41 5.1.99.1
CH3 OOC-CH-COSCoA

CH 3CH2COSCoA

2-Methylaceto2-Methyl-3-4.2.1.17Tiglyl-CoA 2 Methylbutyryl1.1.1.35 1.3.99.3 acetyl-CoA hydroxyCoA butyryl-CoA

COOH

4-P-Pantetheine
2.7.7.3

1.6.5.3

6.4.1.3

COOH (CH3)2CHCHCH(OH)COO (CH3)2CHCH 2COCOO

+ POCH2CH2 NH3

Mevaldate
1.1.1.32

FMNH2
2H
+
4.1.3.1
CH3CH(OH)CH2CO.SCoA

ISOCITRATE
1.1.1.41

(CH3)2CHC(OH)CH 2COO

+ (CH3)2CHCH 2 CH(NH 3)COO

2.7.1.82

Ethanolamine
CH 3COCH 2CH 2N(CH 3)3

2Fe -S (5 Clusters)

2-Isopropylmalate
4.2.1.18
4.2.1.18 1.1.1.3

4.2.1.33

3-Isopropyl- 1.1.1.85 Oxoleucine malate

6.4.1.4
CH3 CH3C = CHCOSCoA

2.6.1.6 1.4.1.9

LEUCINE
1.2.1.25

ADP- OCH2 C(CH 3)2CH(OH)CONHCH 2CH2CO NHCH 2CH2SH

Dephospho-Coenzyme A
2.7.1.24
P-ADP- OCH 2 C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH2SH

3.1.

3.1.4.4 3.1.4.3 2.7.7.15

+ OCH 2CH2N(CH 3)3

2 Acetylcholine CH C(OH)CH CH OH 3 2 2 4.2 Mevalonate

CH COO

4H+

1.6. 5.3

2.3.1.6
+ HOCH 2CH 2N(CH 3)3

MALATE 4H+ 2H+ 4.2.1.2

or 2H+ OOCCH=CHCOO-

-OOCCOCH

GLUTARATE
1.2.4.2 2.3.1.61

2-OXO-

2CH2COO

4.1.1.71

Methylmalonyl-CoA
2.7.2. 4
+ P OOCCH 2CH(NH3)COO

CH3 OOCCH 2C = CHCOSCoA

ASPARTATE
4.3.1.1 6.3.5.4

3-Methylglutaconyl-CoA
H C N

3-Methylcrotonyl-CoA
H2 C
N

1.3.99.10

(CH3)2CHCH 2COSCoA

Isovaleryl-CoA

Coenzyme A

2.7.1.36 2.7.4.2
CH2COO

Choline-P

2.7.1.32

CHOLINE

UQH2

FUMARATE
FADH2
Fe-S Cyt.b
1.3.5.1

Aspartyl-P

CH3C(OH)CH 2CH2OPP + NH 3 CH3(CH2)12CH=CHCH(OH)CHCH 2 O- Galactose

Diphosphomevalonate

SUCCINYL-CoA
6.2.1.4

-OOCCH2CH2CO.SCoA

5.1.99.1 5.4.99.2

1.2 .1.1 1

OOCCH 2CH2CONH CH2 CH-COO OOCCH 2CH2CONH OOCCOCH 2CH2CH2CH-COO OOCCHCH 2CH2CH 2CH-COO + NH3

+ NH3 OOCCH-CH 2CH2CH2CHCOO + NH 3

Psychosine Acyl-CoA
NHCOR CH2 CH3C-CH2CH2OPP

FAD

UQ
4.1.1.33

II

SUCCINATE

-OOCCH2CH2COO-

1.2.1.16

1.3.1.26 OOCCH 2CH2CHO Aspartyl 4.2.1.52 2, 3-DihydroPiperideineSemialdehyde dipicolinate 2, 6-dicarboxylate Succinic semialdehyde OH
+ (CH3)3NCH2CH(OH)CH 2COO + + (CH3)3N(CH 2)3 CH2CH(NH 3)COO

+ OHCCH 2CH (NH3)COO

HC OOCC

CH 2 CH-COO

H 2C OOCC

A M I N O A C I D S

N-Succinyl- 2.6.1.17 N-Succinyl-2, 6 3.5.1.18 Diamino2-amino-6-oxodiaminopimelate pimelate pimelate

+ H2N(CH 2)4 CH(NH 3)COO

Glycine
2.3.1.37

+ + (CH3)3N(CH 2)3 CH2CH(NH 3)COO

UDP-Galactose
3.2.1.46 2.4.1.47 1.3.99.7

UQH2
Isopentenyl-PP
(C5)
1.10.2.2

2H+

+ H2NOCCH 2CH (NH3 COO

Carnitine
2.6.1.19 1.3.99.7

Asparagine
5-Aminolevulinate

1.14.11.1

N6-Trimethyl3-OH-lysine

1.14.11.8

N6-Trimethyllysine

LYSINE

7 5.1.1. 20 4.1.1. 1.5.1.7 - 10

CH3(CH2)12CH=CHCH(OH)CHCH 2 O- Galactose

Cerebroside
CH3 CH3C = CHCH 2OPP

2UQH2

UQH2 1e_ UQ.

OOCCH 2CH 2CH2COSCoA

OOCCH 2CH2CH2COCOO

+ OOCCH 2CH2CH2CH (NH3) COO

+ OHCCH 2CH2CH2CH (NH3) COO

COO NH CHCH 2CH2COO

+ CH 2CH2CH2CH2CH (NH3) COO

4H+

Phytoene
(C40)
2.5.1.32

Dimethylallyl-PP
(C5)
2.5.1.1
CH 3 CH3

2.5.1.29

CH3C= CHCH 2 CH2C= CHCH 2OPP CH2OPP

Geranyl-PP
(C10)
2.5.1.10

2e- 2UQ_ . III 2eFe-S Cyt.bL Cyt.c1 2UQ

1.10.2.2

2H+
TRA

+ R-CH(NH3) COO

4.1.1.70

Glutaryl-CoA

2-Oxoadipate

2.6.1.39

2-AMINO ACID
R-CO-COO

OOCCH 2CH2CH2NH2

2-Aminoadipate 1.2.1.31 2-Aminoadipate semialdehyde

Adenosyl
+

1.5.1.9

Saccharopine

4-Aminobutyrate
(GABA)
4.1 .1 5 .1
H2N(CH 2)3NH(CH2)4NH (CH2)3NH2

CH3-SCH 2CH2CHNH 2

2-OXO ACID
2.6.1.+ OOCCH 2CH 2CH (NH3) COO

Spermine

1eCyt.bH UQ

S-Adenosylmethyl thiopropylamine
(Decarboxylated SAM)
Biosynthesis Degradation

LEGEND
Carbohydrates Amino Acids
Biosynthesis Degradation

NS

MI

Geranyl-geranyl-PP
(C20)

NA TIO N

GLUTAMATE
1.4.1.14

2.7.2.1 + 1 POOCCH2CH 2CH(NH3) COO

2.5.1.22
H2N(CH 2)4NH (CH2)3NH2

Glutamyl-P
1.2.1.41

Spermidine
2.5.1.16
H2NCH2CH2CH2CH2NH2

Phytol (C20)
CH3

CH2OH

OPP CH2

Cyt.c

1.4.1.2

3.5.1.2 6.3.1.2
+ H2NOCCH 2CH2CH (NH3) COO

Lipids
Biosynthesis Degradation

CuA CuA
Farnesyl-PP

or ting ATP nsp 3.6.1.34 synt h tra +oscp

1.6.6.1 1.7.99.4

NO3NO2-

7.1 1.7. 6.4 1.6. .1 8.6 6.3.4.16 1.1

NH4
ATP CO2

Purines & Pyrimidines

Biosynthesis Degradation

Glutamine
6.3.5.5

+ OHCCH 2CH 2CH(NH3) COO

Glutamic semialdehyde
2.6.1.13

Putrescine
CH2 CH2 CH N CHCOO

e as

CH3COCOO

OHCCOO

Vitamins Co-enzymes & Hormones

Biosynthesis Degradation

F1

Pyruvate Glyoxylate
Pentose Phosphate Pathway
4.1.3.16
OOCCH(OH)CH 2COCOO

H2NCOOP

2H+

ATP
AD

Carbamoyl-P
2

+ H 2NCONHCH 2CH2CH2CH(NH3) COO

ATP

CITRULLINE

Pyrroline-5carboxylate
4.1.1.17 1.5.99.8 CH2 1.5.1.2
CH2 CH2 CHCOO

Photosynthesis Dark Reactions

Human Metabolism is identified as far possible by black arrows

Zymosterol

HO H

Lanosterol

5.4.99.7 1.14.99.7

Squalene
(C30)

1/ O 2 2

IV

ADP +

Pi

P +1 P i

T A

2.1.3.3
+ H2NCH2CH2CH2CH (NH3) COO

COOCOOCH3 CH2 CH2 CH2 CH3 -OOC

H 2C H 2C H 2C

CH2 CH2 H 2 C N H H N C H2 N H H N

COOCOOCH2 CH2 CH2 CH2 CH2 CH2 COO-

COOCH2

H 2O
TRA N S L O

H+ H+ H+ H+ H+

2.1.3.3

4-Hydroxy2-oxoglutarate
2.6.1.23
+ OOCCH(OH)CH 2CH(NH 3)COO

Biosynthesis

Degradation

F1

H+ H+

ORNITHINE
F0
H+

NH

6.3.4.5
OOCCHCH 2COO N + H2NCNHCH 2CH 2CH2CH(NH3) COO

PROLINE
1.14.11.2
HOCH H2C N H CH2 CHCOO

COMPARTMENTATION
The "Backbone" of metabolism involves GLYCOLYSIS in the CYTOPLASM, the TCA CYCLE (mainly) in the Mitochondrial matrix and ATP FORMATION spanning the MITOCHONDRIAL INNER MEMBRANE

H2NCONH 2

2.1.4.1

UREA
3.5.3.1 3.5.3.6

CH2 H2NCH2C=O

5-AminoCOOlevulinate -OOC
H2 C H2 C

H+

Glycine +

4-Hydroxyglutamate
HOCH HC

c 0 c-sub-u

nit

+ H2NCNHCH 2CH2CH2CH (NH3) COO

NH2

NO
1.14.13.39

Argininosuccinate

1.5.1.12

CH2 CHCOO

CH 2 CH 2 N H

AT E

D PROTONS

4.2.1.24

H+ H+ H+ H+ ADP Pi

ARGININE
4.3.2.1
+ NH
2

HYDROXY PROLINE
HN C NH CO CH 2 N CH3

OOC

3-Hydroxypyrroline5-carboxylate

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

CH2 CH2 COO-

CH2 COO-

H2 N

ATP
E NDE
RGONIC REACTIO N

+ NH2

+ NH2

Electron Flow

Proton Flow

H2NCNHCH 2COO

4.1.1.37

4.3.1.8 4.2.1.75

Guanidoacetate

2.1.1.2

H2NCN(CH 3)CH2COO

P- HNCN(CH 3)CH2COO

1.5.1.2
Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme Commission (EC) Reference Numbers of Enzymes

Creatine

2.7.3.2

P-Creatine
3.5.2.10

Uroporphyrinogen

Porphobilinogen

Creatinine

22nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England and Sigma-Aldrich
Product No. M 3907

India SIGMA-ALDRICH CHEMICALS PRIVATE LIMITED Telephone Bangalore: 91-80-5112-7272 Hyderabad: 91-40-5531 5548 / 2784 2378 Mumbai: 91-22-2579 7588 / 2570 2364 New Delhi: 91-11-2616 5477 / 2619 5360 Fax Bangalore: 91-80-5112-7473 Hyderabad: 91-40-5531 5466 Mumbai: 91-22-2579 7589 New Delhi: 91-11-2616 5611 Ireland SIGMA-ALDRICH IRELAND LTD. Free Tel: 1800 200 888 Free Fax: 1800 600 222 Israel SIGMA-ALDRICH ISRAEL LTD. Tel: 08-948-4100 Fax: 08-948-4200

Italy SIGMA-ALDRICH S.r.l. Telefono: 02 33417310 Fax: 02 38010737 Numero Verde: 800-827018 Japan SIGMA-ALDRICH JAPAN K.K. Tokyo Tel: 03 5821 3111 Tokyo Fax: 03 5821 3170 Korea SIGMA-ALDRICH KOREA Tel: 031-329-9000 Fax: 031-329-9090 Malaysia SIGMA-ALDRICH (M) SDN. BHD Tel: 603-56353321 Fax: 603-56354116 Mexico SIGMA-ALDRICH QUMICA, S.A. de C.V. Free Tel: 01-800-007-5300 Free Fax: 01-800-712-9920

The Netherlands SIGMA-ALDRICH CHEMIE BV Tel Gratis: 0800-0229088 Fax Gratis: 0800-0229089 Tel: 078-6205411 Fax: 078-6205421 New Zealand SIGMA-ALDRICH PTY., LIMITED Free Tel: 0800 936 666 Free Fax: 0800 937 777 Norway SIGMA-ALDRICH NORWAY AS Tel: 23 17 60 60 Fax: 23 17 60 50 Poland SIGMA-ALDRICH Sp. z o.o. Tel: (+61) 829 01 00 Fax: (+61) 829 01 20 Portugal SIGMA-ALDRICH QUMICA, S.A. Free Tel: 800 20 21 80 Free Fax: 800 20 21 78

Russia SIGMA-ALDRICH RUSSIA TechCare Systems, Inc. (SAF-LAB) Tel: 095-975-1917/3321 Fax: 095-975-4792 Singapore SIGMA-ALDRICH PTE. LTD. Tel: 65-6271 1089 Fax: 65-6271 1571 South Africa SIGMA-ALDRICH SOUTH AFRICA (PTY) LTD. Tel: 27 11 979 1188 Fax: 27 11 979 1119 Spain SIGMA-ALDRICH QUMICA S.A. Free Tel: 900101376 Free Fax: 900102028

Sweden SIGMA-ALDRICH SWEDEN AB Tel: 020-350510 Fax: 020-352522 Outside Sweden Tel: +46 8 7424200 Outside Sweden Fax: +46 8 7424243 Switzerland FLUKA CHEMIE GmbH Swiss Free Call: 0800 80 00 80 Tel: +41 81 755 2828 Fax: +41 81 755 2815 United Kingdom SIGMA-ALDRICH COMPANY LTD. Free Tel: 0800 717181 Free Fax: 0800 378785 Tel: 01747 833000 Fax: 01747 833313

United States SIGMA-ALDRICH P.O. Box 14508 St. Louis, Missouri 63178 Toll-free: 800-325-3010 Call Collect: 314-771-5750 Toll-Free Fax: 800-325-5052 Tel: 314-771-5765 Fax: 314-771-5757 Internet: sigma-aldrich.com

sigma-aldrich.com/pathways