Professional Documents
Culture Documents
HY A L UR ONIC A C ID P E P T IDOG LY C A N C H
6.3.2.7-10 6.3.2.13 HO O
C H 3C H C OO2 OH
DE R MA T A N
C HIT IN
OP P U
C HONDR OIT IN
O C OO -
G LY C OG E N
HO C H 2 OH O O OH OH OH OH OH C H 2 OH O NH
C ONH 2 C H 2 C OO OH NH
C OO O O
R ibos e
+
-O - P - O - P - OO O
Adenos ine(P )
C OO
R ibos e
-O-P -O-P -O
O O
-Adenos ine
2.7.7.18
+ N
NIC OT INA T E
2. 4. 2. 11
N
C OO
C OO
+ C OO N RP
O C OO OP C
Indoleac etate
(A uxin)
1.2.3.7
C H 2 C HO
Indoxyl
HO NH
NA D( P )
+ C H 2 C H(NH 3)C OO HO NH NH
6.3.5.1 6.3.1.5
C H 2 C H 2 NH 2
R ibos e- P
Des amino-NA D
HO
2.4.2.19
C H 2 C H 2 NHC OC H 3
Quinolinatenuc leotide
N
C H 2 OH
HO
2.4.99.7
2.4.2.19
NHAC
2.4.1.17
HO
OH
OP P U OH
L A C TOS E
C H 2OH O OH OH OH
C H 2 C H 2 NHC OC H 3
C OO C OO
UDP Iduronate
5.1.3.12
C OO HO OH O
G DP -F uc os e
4.2.1.47
C H 2 OH O
G DP Mannuronate
T DP -R hamnos e
O OP P T OH
3.2.1.23 2.7.1.38
5.1.3.13 O 2.4.1.33
C H 2 OH O HO OH HO OH
Indoleac etaldehyde
4.1.1.43
C H 2 C OC OO
NH
Indole
1.14.16.4
5-Hydroxytryptophan
+ C O C H 2 C H(NH 3 )C OO C HO
4.1.1.28
5-Hydroxytryptamine
(S E R OTONIN)
2.3.1.5
NH
2.1.1.4
Quinolinate
OH
2.4.1.16 1.1.1.158
C H 2 OH O
HO OH HO OP P G
3.1.3.29
HO
G DP -Mannos e
OP P U OH C H 2 OH O
T DP -4-Oxo6-deoxygluc os e
4.2.1.46
A DP G luc os e
C H 2OH O OH HO OH HO
G A L A C TOS E
2.7.1.6
OP P U HO C H 2 OH O OH OP OH
+ C O C H 2 C H(NH 3 )C OO NH 2 OH
+ C O C H 2 C H(NH 3 )C OO NH 2
Indolepyruvate
2.4.1.22
NH
4.1.99.1
F ormylkynurenine
1.13.11.11
+ C H 2 C H(NH 3 )C OO NH
NH
3.5.1.9
N-A c -Neuraminate
(S ialate)
C H 2O P O
HO O C H2 C C OO
OP P U NHAC
3.7.1.3
2.7.7.13
MA NNOS E
2.7.1.7
C H 2O P O
G DP -G luc os e
1. 1. 1. 22
2.7.7.27 2.7.7.34
C H 2 C H 2 NH 2
HO OH HO O P
5.1.3.7
HO OH OH
Mannos e-1-P
5.4.2.8
5.1.3.6
T DP -G luc os e
2.7.7.24
C H 2 OH O OH OP P U OH
T ryptamine
C OO OC P OC H 2 C H 2 HOC H HC OH C
NH
4.1.1.28
4.2.1.20
T R Y P TOP HA N
HO C OO C OO OH OH OH OH
Indole-3-glyc erol-P
C OO HO OH
4.1.1.45 3-Hydroxy 1.13.11.6 2-A mino-3-c arboxy 2-A minomuc onateanthranilate muc onate s emialdehyde 6-s emialdehyde C OO H H C atec hol
NH C C C H C H 2O P C OO NH 2
OC H NH 2 C OO
A R O M A T I C A M I N O A C I D S
1. 4. 1. 19
1.2.1.32 1.14.12.1
OOC OOC C H 2 C OC OO NH 2
OH OH
2.7.7.12
4.1.1.48
2.4.2.18
A nthranilate
OOC
C OO
4.1.3.20
OP P U
HO OH HO OH
C H2
4.1.3.27 5.4.99.5
OH
H E X O S E S
AC NH HO OH OH
2.7.1.60
HO OH NHAC HO OH
Mannos e-6-P
2.4.1.9
2.4.1.13
C H 2O P O HO OH OH NH 2
OP
5.1.3.14
2.7.7.23
OH
NHC OC H 3
G luc os e-1-P
3-Deoxy-D-arabinoheptulos onate-7-P
O -OOC O C H 2 C OO
OH
4.6.1.3
O
Dehydroquinate
4.2.1.10
Dehydros hikimate
C H 2 C OO
1.1.1.25
S hikimate
OH
P O
2.7.1.71
OH
C H 2 C OC OO
S hikimate-3-P PEP
OH
OH
P O
2.5.1.19
OH
O-C -C OO
C horis mate
+
OH
OC -C OO
P rephenate
C H 2 C OC OO
C H 2 C H (NH 3 ) C OO
C H 2 C H(NH 3 ) C OO
2. 3. 1.
5.3.1.8
OH H HOC H 2 C H C
OH OH C C H
HOC H 2
G luc os amine-6-P
3.2.1.26 3.2.1.48
HO OH
OH
OH
C OO -
OH OH H
HO OH
OH OH
HO OH
OH H OH H
G ulonate
3.1.1.18 HOC H 2
C H C C H O
1.1.1.19
OH OH C H CO
G luc uronate
OH H HOC H 2 C H C OH C H O
1.13.99.1
CO CO
Inos itol
HOC H 2 C H
3.1.3.25
OH H C
OH
F ruc tos e
1.1.1.14
H H C OH H C C C H 2 OH OH
S UC R OS E
5.5.1.4
G L UC OS E
5.4.2.2 3.1.3.9 2.7.1.2 2.7.1.1
F umaryl 5.2.1.2 Maleyl 1.13.11.5 Homogentis ate ac etoac etate ac etoac etate
C HOHC H 2 NHC H 3 OH OH C HOHC H 2 NH 2 OH
C OO
O C H 2 C OO
4.2.1.51 1.3.1.13
OH
1.13.11.27
OH
2.6.1.5
OH
T Y R OS INE
1.14.16.1
P HE NY L A L A NINE
1.3.1.13
2.6.1.5 4. 3. 1. 5
P henylpyruvate
Inos itol-P
C CO
HOC H 2 C
C H 2 C H 2 NH 2
+ C H 2 C H (NH 3 ) C OOOH
4 .1
.1 .2
OH OH C O
C H 2O P O
1. 1. 1.
21
2.6.1.16
ATP
E pinephrine
(A drenaline)
2.1.1.28
OH
Norepinephrine
(Noradrenaline)
.1 .6 2 .1
1.14.17.1
Dopamine -T oc opherol
(V itamin E )
OH
4.1.1.28 1.14.18.1
O
Dopa
H2 C C H-C OO + NH 3
OH
1.14.16.2
Ubiquinone
O O
C H 2 C H 2 NH 2
C H=C HC OO
+ C H 2 C H (NH 3 ) C OO
T yramine
OH
C innamate Menaquinone
1.14.13.11
C H=C HC OO
A S C OR B A T E
OH H HOC H 2 C H C CO O
1.10.2.1 1.10.3.3
CO
OH OH H
S orbitol
2.7.1.3
H P OC H 2 C H C OH H C C C OO -
2. 7
CO
. 1.
HO OH
A DP
C HOHC H 2 NH 2 OC H 3
HN
P E N T O S E S
3-Dehydrogulonate
OH H HOC H 2 C H C OH C C HO
1.1.1.130
H
2, 3-Dioxogulonate
H C OH C C HO H HOC H 2 C H C
Dehydroas c orbate
C O C H 2 OH H H C OH C CO
.1 3 .1
.1 7
OH
1.1.1.49
G luc os e-6-P
5.3.1.9
C H 2 OP O OH OH
I O
C H(OH)C OO OC H 3 OH
HO OH
Normetepinephrine
.3 .4
OH
C oumarate
C HOHC H 2 OH OC H 3 OH
(Normetadrenaline)
O O
NH
OH
I
OH
HOC H 2
OH H
OH OH H
L -Xylos e
OH H HOC H 2 C H C H C OH OH
4.1.1.34
C H 2 OH
D-A rabinos e
OH H HOC H 2 C H H C OH OH H C C OH CO
5.3.1.3
OH OH
D-R ibulos e
OH H P OC H 2 C H H C OH OH H C C OH C HO CO
2.7.1.47
HOC H 2 C
C H 2O P
4-OH-3-MethoxyD-mandelate
C H 2O P O NHC OC H 2 NH 2 H 2C OC NH C HO NH RP
1 .4
4-OH-3-Methoxyphenylglyc ol
NH H 2C C
1.14.18.1
ME L A NIN
T HY R OXINE
OOC -C H-C H 2 C OO HNC O C N
L IG NIN
T annins
O C
P lant P igments
NADP +
OH OH H
1.1.1.44 5.1.3.1
H H C C O C H 2 OH H P OC H 2 C H C
H C
HO C C O C H 2 OH
2.2.1.1
P OC H 2 C
C H 2 OH
L -A rabitol
OH OH H HOC H 2 C H C H C OH C HO
L -Xylulos e
HOC H 2 C
2.7.1.53
NA DP H
L -Xylulos e-5-P
HOC H 2 C OH H
C H 2 OH P OC H 2
OH OH H
HN
C HO NH RP
H 2N
HC C
N CH N
OOC
N C C CH N RP
N C C N CH RP O C C NH C N CH N RP
OH OH OH
C H 2 OH
R ibitol
H H C
OH
OH
2.1.2.2
6.3.5.3 6.3.3.1 F ormyl F ormyl 5-A mino 4.1.1.21 5-A mino-4-imidazole 6.3.2.6 5-A mino-4-imidazole 4.3.2.2 5-A minoimidazole c arboxylate-R P (N-s uc c inylc arboxamide)-R P c arboxamide-R P glyc inamide-R P glyc inamidine-R P imidazole-R P
H 2 NC ONH 2
RP
H2N
H 2N
CH
H 2N H 2N
RP
C A T E C H O L A M I N E S
OH OH
1.1.1.10
OH H OH OH
L -A rabinos e
OH H HOC H 2 C H C H C OH OH
5 .3
.1 .4
HOC H 2
Xylitol
C H C H
2.7.1.47
D-Xylos e
OH OH P OC H 2 C H C H CO C H 2 OH
H C C HO
3.1.3.11
2.7.1.11
HOC H 2 C
E rythros e-4-P
P OC H 2
OH OH
A DP
HO C C O C H 2O P C H 2O P O
Urea
H 2N
OC
C OO C N H H
NH 2 CO
NH
H2N
OC
OC C N H H
NH CO NH
HN OC
NH C C CO NH HN OC
O C NH
N C C CH NH HN HC
O C N
2.1.2.3
N C C CH NH
H2N HC O
H C
H C
3.5.3.4
C HO
C O C H 2 OH
D-R ibos e
5.1 .3. 4
OH OH OH
L -L yxos e
5.3.1.6
OH OH H
.9
HOC H 2
2 .7
2.7.1 .17
4.1.2.-
.1 .1
OH H
2.2.1.2
D-Xylulos e-5-P
NH 2
.1 .4 2 .6 .1 0 .1 20 1 .4 1. 1.
G LY C INE
O
C H 2 (NH 3 )C OOH
A llantoate
NH 2
3.5.2.5
A llantoin
O O O HC
1.7.3.3
N NH 2 N
UR A T E
N CH N
N
N H
3. 2. 2.
Inos ine
2.4.2.1
3. 1. 3.
F ormylamidoimidazolec arboxamide-R P
3.5.4.10
HN O C N N C C N CH RP HC
N O P O O
HC
N
CH
OH H
D-Xylulos e
H+
PHOTOSYSTEM II
OH OH H H C H C C HO P OC H 2
H+
H+
c otophosphoryla SYSTEM n-cycli electr 2H+ yclic Ph tion l No (electric curre on fl C nt) o H+ 2H+
PHOTO- H+
P OC H 2 C
H C
H C
H OH C C C O C H 2O P
P -R ibos yl amine
4.1.2.13
G lyoxylate
S arc os ine
2. OOC C H 2 NHC H 3
N C H2 O
-O P ~O P ~O P O C H 2 O O O O
NH 2 N C C CH C HC N R P (P ) N
OOC -C H-C H 2 C OO
F umarate
OH
1.5.99.2
OOC C H 2 N(C H 3 ) 2
C yc lic A MP
1.4.4.2
4.6 .1. 1
ATP
d-A DP
2.7.4.6
2.7.4.6
OH OH
A DP
2.7.4.3 2.7.4.4
A DE NOS INE -P
(A MP )
4.3.2.2
NH N C C N CH C HC NH R P N
A s partate
6.3.4.4 3.1.4.6 2.4.2.1
INOS INE -P
(IMP )
HN O C N N C C CH N RP
1.17.4.1
A denylos uc c inate
3. 5. 4. 3
A denine
2.7.7.7
1.1.1.205
OC
OH OH OH
Dimethylglyc ine
2.1.1.5
OOC C H 2 N(C H 3 ) 3
+
3 3
H 2O
H+ H+
Translocated protons
O2
H+
H+
2 2
H+
H+
H+
THYLAKOID LUMEN
H+
C OO
L inoleate
1.3.1.35
1.14.99.25
C OO
-L inolenate
A rac hidonate
C O-S -AC P
L I P I D B I O S Y N T H E S I S
C OS C oA
1.14.99.5
Oleoyl-C oA S tearoyl-C oA
C H 3 (C H 2 ) 14 C OS -AC P C OS C oA
P almitoyl-A C P A C Y L -A C P
C H 3 (C H 2 ) 6 C H 2 C H 2 C OS AC P
3-E noyl-A C P
4.2.1.60 4.2.1.61
Dec anoyl-A C P
1. 3. 1.
3, 4-Dec enoyl-A C P
9
C H 3 (C H 2 ) 5 C H=C HC H 2 C OS AC P C H 3 (C H 2 ) 6 C H=C HC OS AC P
4. 2. 1.
4 .2 .1
C H 3 (C H 2 ) 2 C H 2 C H 2 C OS AC P
Hexanoyl-A C P
1.3.1.9
4.2.1.59
C H 3 C H 2 C H 2 C OS AC P
B utanoyl-A C P
1.3.1.9
C rotonoyl-A C P
R -C H 2 C OO
4.2.1.58
A C Y L -C oA
(C ytos ol)
2.3.1.7
C H 3 (C H 2 ) n+2 C OS -C oA
6.2.1.3
3.1.2.20
F A T T Y A C ID
L I P I D D E G R A D A T I O N
3.1.1.3
R -C O-OC H
FAT
Diac yl
C H 2 OH
A C Y L -C oA
(Mitoc hondria)
C H 3 (C H 2 ) n C H=C HC OS C oA C H 3 (C H 2 ) 2 C H=C HC OS C oA
2, 3-E noyl-C oA
C H 3 (C H n C H(OH)C H 2 C OS C oA
C H 3 (C H 2 ) 2 C H 2 C H 2 C OS C oA
Hexanoyl-C oA B utanoyl-C oA
C H 3 C H 2 C H 2 C OS C oA
C H 3 (C H 2 ) 2 C H(OH)C H 2 C OS C oA
P entanoyl-C oA
C H 2 O-C O-R R '-C O-OC H O C H 2 O-P O O
C H 3 C H 2 C H 2 C H 2 C OS C oA
OH
OH
R '-C O-OC H
1.3.99.7
HO OH OH
C OO O + C H 2 O P O C H 2 C HNH 3
R '-C O-OC H
2.7.8.8 2.7.8.11
C H 2 O-C O-R
S erine
Inos itol
R '-C O-OC H
P H O S P H O L I P I D S
4.1.1.65
O HC O-C O-R
+ C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 2.1.1.17 O C H 2 OC H=C HR 2.1.1.71 C H 2 O-C O-R R -C O-OC H O 3.1.1.32 O R '-C O-OC H + + C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 O O
O + C H 2 O P OC H 2 C H 2 NH 3
C ardiolipin
2.7.8.1
C DP -E thanolamine
C H 2 O-C O-R HOC H O
+ C P P - OC H 2 C H 2 NH 3
2.7.7.14
E thanolamine-P
C H 2 OH HOC H O + C H 2 OP O C H 2 C H 2 N(C H 3 ) O
- L ys olec ithin
3.1. 1.5
L E C IT HIN
+ C P P -O C H 2 C H 2 N(C H 3 ) 3
2.7.8.2
C DP -c holine
.3
+ NH 3 C H 3 (C H 2 ) 14 C H(OH)C HC H 2 OH
1.1.1.102
S phinganin
+ NH 3 C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 OH
2 .7 .8
3.1 .4. 12
4-S phingenin
3.5.1.23
NHC OR
2.4 .1. 62
S P HING OMY E L IN
2.7.8.3
C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 OH
3.1.4.12
C eramide
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
L yc opene -C A R OT E NE
C OO -
(C 40)
T o B rain V IS ION
(C 40)
hv R hodops in
C H 3O C H 3O O O C H3 n
Metarhodops in
1.13.11.21
Ops in
C HO
R etinoate
1.2.1.36 1.1.1.105
(C oenzyme Q)
5.2.1.3
Ubiquinone
trans -R etinal
L ight
11-c is -R etinal
1.1.1.105
C HO
R etinol es ters
2.3.1.76 3.1.1.21
C H 2 OH
CH3
O C H3
(V itamin A )
(V itamin K )
(V itamin E )
6.
Dark
2.5.1.21
F6
N2
3. 5
5.2.1.7
11-c is -R etinol
P hylloquinone
-T oc opherol
.5
C H 2 OH
HO
HO H
H HO H
1.9.3.1
P regnenolone
C HOL E S T E R OL
Zymos terol
L anos terol
5.4.99.7 1.14.99.7
S qualene
(C 30)
1/ O 2 2
IV
HE MOG L OB IN
C H2 CH H 3C HC N H3C C H2 C H2 C OO C H H C N Fe N C H3 C H2 C H2 C OO H 3C CH C H3 CH CH H 3C
C HL OR OP HY L L
C H2 CH H2 C N H H C H2 C H2 N C H3 C H2 C H2 C OO H 3C C H3 C H 2 CH H3C
H 2C
C OO C OO H2 C N H H C H2 N C H3 C H2 C H2 C OO C H3 C H2 C H2 C H2 - OOC
H 2C H 2C
C H2 N H N H
C H2 C H2 N H N
H 2C
C OO H2 C N H H N C H2 C H2
C OO C H2
COOCH2
H2O
TR A NS L O
Pi AD P + H+ H+ H+ H+ H+
P +1 P i
T A
N H N H
H2C
C H2 C H2 C OO -
C H2 C H2 C OO -
HE ME
1.3.3.4 4.99.1.1
P rotoporphyrinogen
1.3.3.3
C oproporphyrinogen
www.iubmb.org
A rgentina SIGMA-ALDRICH DE ARGENTINA, S.A. Tel: 54 11 4556 1472 Fax: 54 11 4552 1698 A ustralia SIGMA-ALDRICH PTY., LIMITED Free Tel: 1800 800 097 Free Fax: 1800 800 096 Tel: 612 9841 0555 Fax: 612 9841 0500 A ustria 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 z ld telefon: 06-80-355-355 Ingyenes z ld fax: 06-80-344-344
H+
P H O T O S Y N T H E S I S
Ferredoxin
2eQB QA
Pheophytin P680 Chl.a Mn
2e-
PQ PQH2 PQH2
_ PQ
1e-
2e-
*2e
Fe-S
H+
S edoheptulos e-P P
2.2.1.1
P OC H 2C HOHC HO
OH OH OH H
2 .7 .7
.7
DNA R NA
O C
H+
d-A T P
2.1.2.1
2. 7. 7. 7
2.4.2.15
d-G DP
2.7.4.6
XA NT HOS INE -P
(XMP )
2. 4. 2. 1
6.3.4.1 6.3.5.2
HN H 2N C O C N N C C CH N RP
P U R I N E S
1 .1
B etaine
1.2.1.8
+
2 .7
2.7.7.6
7 .4
1e-
PQ
Cyt bf
2e-
H+
H+ H+
NADP+
A1 Chl.A0
._
2e-
2PQ
PC
NADPH+H+
H+ H+ H+
Dihydroxyac etone-P
(G lyc erone-P )
HOC H 2 C OC H 2 OP
2.2.1.1
Pi
Pi NA D+
1.2.1.12
2.4.2.14 6.3.4.7
OHC C H 2 N(C H 3 ) 3
B etaine aldehyde
1.1.99.1
F OL IC A C ID C1 P OOL
4.1.2.5
ATP
4. 2. 1. 20
2.7.7.6
.7 .7
.1
G uanine G DP
2.7.4.8
2 .7
.7 .6
O C
.6
1. 17 .4
.1
O C
G UA NOS INE -P
(G MP )
NH 2 C CH N CH OC N DP
P700
PC PC
Pi
A DP
1
ADP
Pi
Glyceraldehyde
+ HOC H 2 C H 2 N (C H 3) 3
C H3 H 2 NC H 2 C HC OO
C H3 H 2 NC ONHC H 2 C HC OO
HN OC
C H-C H 3 CH2 NH
HN OC
4H +
Ribulose-1,5-bis-P
1.2.1.13
C H 2O P O
C HOL INE
2.6.1.51 1.4.1.7
ATP
Fixation
CO2
NA DH
HOC H 2 C H(NH 3 )C OO
3.5.1.6
S E R INE
4.2.1.22 4.1.1.11
H 2 NC H 2 C H 2 C OO
2. 1
-Ureido is obutyrate
. 1. 13
3.5.1.6
3.5.2.2
Dihydro thymine
3.5.2.2
C C H3 CH NH O C
T DP
2.4.2.4
O C
2 .7
.4 .9 HN
OC
C -C H 3 CH DP
2.1.1.45
HN OC
1.3.1.2
T hymine
HN OC
T HY MIDINE -P
2 .4 .2 .4
d-UMP
N
CH CH N DP 3.5.4.12 NH 2 C CH CH OC NH O C
d-C MP
2.7.4.14
d-C DP
HN
H 2 NC ONHC H 2 C H 2 C OO OC
2.7.6.1
OH OH
OP OP
P OC H 2C HOHC OO P
HOC H 2 C OC OO
-A lanine
-OOC NH
ATP
ATP synthase
3.6.1.34
ATP
HO C OO
P -R ibos yl-P P
Hydroxypyruvate
3.1.3.3
C arbamoyl -alanine
HN OC O C NH
Dihydrourac il
HN OC O C
C H2 C H2 NH
1.3.1.2
N H
CH CH
1.17.4.1
Urac il
O C
3.5.4.1
O C HN OC
C ytos ine
CH CH
NH 2
C DP
A DP
+ P OC H 2 C H(NH 3 )C OO
2 C H2 OC C H-C OO N
C H2 C H-C OO
C arbamoyl as partate
2.6.1.22
H P OC H 2 C H C H C H C
3.5.2.3
UR IDINE Dihydro Orotate Orotidine-P Uridine-P UDP 4.1.1.23 (UMP ) 2.7.4.4 2.4.2.10 2.7.4.6 triphos phate orotate 1.3.1.14
(UT P )
H P OC H 2 C H C H C H C NH 2 N OC C NH CH C HC N N H P OC H 2 C H C CO C H2 C ONH 2 NH C C HC N N CH N RP
CH C -C OO NH
HN
CH
C -C OO OC N RP
CH OC N C H RP HN
2.4.2.9
N OC
N R PPP
C H 2.7.4.6 CH
6.3.4.2
RPPP
P Y R I M I D I N E S
a
c
C OO
HO
ATP
OH C OO HO O OH
1.1.1.29
NH 2 N + C C N CH C HC N N R P (P P )
1.13.11.34
O
5. 1 .1 3 . 9 9 4 .9 . 3 9 .1
L eukotriene B 4
C OO
P OC H2C HOH C OO
1.1.1.95
P -Hydroxypyruvate
2.4.2.17
HC N
P OC H 2 C OC OO
OH OH O
P -R ibos yl-A T P
C
3.6.1.31
P -R ibos yl-A MP
C CH NH + C H 2 C H(NH 3 )C OO
3.5.4.19
OH OH O
OH OH
P OC H 2 C
P ros taglandin P G E2
C H 3 (C H 2 ) 14 C H(OH)C H 2 C OS -C oA
HO
OH
5.3.99.5
OH-S tearoyl-C oA
P OC H2 C H(O P ) C OO
5.4.2.1
G lyc erate
C C H 2 C HC OO NH NHC OC H 2 C H 2 NH 2
H
HC N
C arnos ine
4.1.1.22
HC N CH
C NH
RP
OH OH HN
C H 2 C H(NH 3 )C H 2 OP
C H 3 (C H 2 ) 14 C OC H 2 C OS -C oA
ACE TATE
C H 3C OO
HIS T IDINE
4.3.1.3
1.1.1.23
His tidinal
OOC HN
1.1.1.23
His tidinol
OC N
NH CH
3.1.3.15
His tidinol-P
NH CH
4.2.1.19
2.6.1.9
CH N C
3-OH-A c yl-A C P
1.1.1.100
3-Oxoac yl-A C P
C H 3 (C H 2 ) n C OC H 2 C OS AC P
Imidazole ac etol-P
CH C HC OO
HC
C C H NH
C H 2 C H 2 NH 2
1.2.1.4
C H 3 C H 2 OH
C HC H 2 C H 2 C OO NH CH
C HC H 2 C H 2 C OO NH CH
HIS T A MINE
2.3.1.41
E T HA NOL
1.1.1.1
2.1.3.2
2 .3
F ormimino glutamate
3.5.2.7
Imidazolone propionate
4.2.1.49
NH CH
4.3.1.3
60 C H 3 (C H 2 ) 6 C H(OH)C H 2 C OS AC P
.6 0
3-OH-Dec anoyl-A C P
C H 3 (C H 2 ) 2 C H(OH)C H 2 C OS AC P
1.1.1.100
3-Oxo-Dec anoyl-A C P
2.3.1.41
C H 3 (C H 2 ) 2 C OC H 2 C OS AC P
C H 3 (C H 2 ) 6 C OC H 2 C OS AC P
.1 .3
+ C H 2 C O-OC H 2 C H(NH 3 )C OO
A c etyls erine
+ S -C H 2 C H(NH 3 )C OO + S -C H 2 C H(NH 3 )C OO
HS
.9 9
3-OH-Hexanoyl-A C P
C H 3 C H(OH)C H 2 C OS -AC P C H 2 OH HOC H C H 2 OH
1.1.1.100
3-Oxo-Hexanoyl-A C P
C H 3 C OC H 2 C OS AC P
P -enolpyruvate
A DP Malonyl-A C P
2.3.1.39
HOOC C H 2 C O-S -AC P
C H 2 =C (O P ) C OO
1.8.99.1
HS O -
1.8.99.2
A c etaldehyde HS
4 .1 .1 .1
C H 3 C HO
2.7.1.25
A denylyls ulphate
(A P S )
2.7.7.4
4 .2
+ .8 HS C H 2 C H(NH 3 )C OO
2.3.1.41
C Y S T INE
4.4 .1.1 5
1.6.4.1
C Y S T E INE
4.4.1.1 4.2.99.9
+ C H 2 C H(NH 3 )C OO + S C H 2 C H 2 C H(NH 3 )C OO
C ys tathionine
+ HS C H 2 C H 2 C H(NH 3 )C OO
+ C H 3 S C H C H C H(NH )C OO 2 2 3
Homoc ys teine
3.3.1.1
2.1.1.13 2.1.1.14
ME T HIONINE
+ C H 3 S C H C H C H(NH )C OO 2 2 3 +
3-OH-B utanoyl-A C P
HOC H
1.1.1.100 1.1.1.8
C H 2 OH C H 2O P
A c etoac etyl-A C P
2.3.1.41
1.13.11.20
+ HO 2 S C H 2 C H(NH 3 )C OO + HO 3 S C H 2 C H(NH 3 )C OO
2.7.1.40
G lutamate
.1 .2
6 .3 .2 .2
Adenos yl
Adenos yl
2.5.1.6
G lyc erol
2.3 .1.1 5
2.7.1.30
2.3. 1.51
C H 2 O-C O-R
3 .7
.1 .2
ATP
4.4 .1. 15
HS O 3
+ C H 3 C H(NH 3 )C OO
R -C O-OC H C H 2O P
2.7.8.5
HOOC C H 2 C O-S C oA
P Y R UV A T E
1.2.4.1 2.3.1.12 1.8.1.4
1.4.1 .1
2.6.1.2
HO 2 S C H 2 C OC OO
C ys teine s ulphinate
C ys teate
4 .1
A L A NINE
4.1.1.29
Hypotaurine
HO 2 S C H 2 C H 2 NH 2
1.8.1.3
HO 3 S C H 2 C H 2 NH 2
+ S C H 2 C H 2 C H(NH 3 )C OO
2.1.1.10 2.1.1.20
S -A denos yl methionine
(S A M)
T aurine
-G lutamylc ys teine
6 .3 .2 .3
G lyc ine
4.1.1.4
1.1.1.30
P hos phatidate
A c etoac etate
3.1.2.11
C H 3 C OC H 2 C OO
4.1.1.9
4. 1. 3.
18
+ OOC C H 2C H 2 C OO C H 2 C H 2 C H(NH 3 )C OO
4.1.1.12 2.6.1.18
C H 3 C H(OH)C OO
S uc c inylhomos erine
2.3.1.46
C H3 C H3
1 .1
CH3COCOO-
.1 .2
P Y R UV A T E
3-OH-A c yl-C oA
1.1.1.35 1.1.1.35
C H 3 (C H 2 ) n C OC H 2 C OS C oA
LACTATE
4. 2. 1. 52
1.2.1.18
4.1.1.32
4. 1. 3.
18
+ P OC H 2 C H 2 C H(NH 3 )C OO
+ HOC H 2 C H 2 C H(NH 3 )C OO
B ile A c ids
HC HO
4.1.2.12
C H3 + C HC H(NH 3 )C OO C H3
G lutathione
HOC H 2 C (C H 3 ) 2 C OC OO
Oxopantoate
3-Oxoac yl-C oA
2. 3. 1.
2. 3. 1.
16
C H 3 (C H 2 ) 2 C OC H 2 C OS C oA
16
NA D ATP C O2
6.4.1.1
4.2.1.16
C H 3 C H 2 C OC OO
C (OH)C H(OH)C OO
C HC OC OO
1.1.1.169
C H 3 C OC (OH)C H 3
1.1.1.86
2-3-Dihydroxy is ovalerate
C H3
4.2.1.9
2.6.1.32
1.1.1.157
2.3 .1.9
1.2.1.25
HOC H 2 C (C H 3 ) 2 C H(OH)C OO
NADH+H+
CH3COSCoA
1.1.1.35
3-Oxopentanoyl-C oA
OHC C OO
4.1.3.5
NAD+
2.6 .1.4 2.6 .1.4 4
1.1.1.39
A C E T Y L -C oA
Methylmalonyl s emialdehyde
2. 3. 1. 16
C H3 OHC C HC OO
1. 1. 1.
31
3-Hydroxyis obutyrate
C OO C H 3 C OC (OH)C H 2 C H 3
3.1.2.4
HOC H 2 C HC OS -C oA-
C H 2 = C C OS C oA
C H 3 C HC O-S C oA
P A NTOT HE NA T E
2.7.1.33
P OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C OO
O O
2.7.7.41
G lyoxylate
1.1.1.79 1.2.3.5
HOC H 2 C OO
4.1.3.5
C H 2 C OO C H 3 C (OH)C H 2 C OS C oA
4.1.3.4
C H 2 O P OC MP
NA DH+H +
4. 2. 1. 18
-OOCCOCH COO2
OX A L OA C E T A T E
NAD+
4.1.3.7 4.1.3.8
2.6.1.1
CH2COOC(OH)COOCH2COO-
G lyc olate
1.2.1.21 2.7.8.5
HOC H 2 C HO
-OH--Methylglutaryl-C oA
1.1.1.34
C H 3C H 2
2.6.1.32
C H 3C H 2
IS OL E UC INE
CH3
1.2.1.25
HOOC -C OOH
Oxalate
F MN
I
I
1.1.1.37
C IT R A T E
4.1.3.2
G lyc ol aldehyde
1.4.3.8
+ HOC H 2 C H 2 NH 3
C H 2 C OO C H 3 C (OH)C H 2 C HO
Glyoxylate Cycle
-OOCCHO
4.2.1.3
CH(OH)COO CHCOOCH2COO-
P ropanoyl-C oA
2.1.3.1 4.1.1.41 5.1.99.1
C H3 OOC -C H-C OS C oA
C H 3 C H 2 C OS C oA
C H 3 C H 2 C HC OS C oA
4-P -P antetheine
2.7.7.3
1.6.5.3
6.4.1.3
+ P OC H 2 C H 2 NH 3
Mevaldate
1.1.1.32
C H 2 C OO
F MNH 2
2H
+
4.1.3.1
CH3CH(OH)CH2CO.SCoA
C OOH
IS OC IT R A T E
1.1.1.41
(C H 3 ) 2 C HC (OH)C H 2 C OO
2.7 .1. 82
E thanolamine
C H 3 C OC H 2 C H 2 N(C H 3 ) 3
2F e -S (5 C lusters)
2-Is opropylmalate
4.2 .1. 18
4.2.1.18 1.1.1.3
(C H 3 ) 2 C HC HC H(OH)C OO
(C H 3 ) 2 C HC H 2 C OC OO
2.6.1.6 1.4.1.9
+ (C H 3 ) 2 C HC H 2 C H(NH 3 )C OO
L E UC INE
1.2.1.25
A c etylc holine
.4 .2
2.3.1.6
3 .1
C H 3 C (OH)C H 2 C H 2 OH
4H+
Mevalonate
2.7.1.36 2.7.4.2
C H 2 C OO
1.6. 5.3
-OOCCOCH CH COO2 2
G L UT A R A T E
1.2.4.2 2.3.1.61
2-OXO -
4.1.1.71
Methylmalonyl-C oA
2 .7 .2 .4
AS PAR TATE
4.3.1.1 6.3.5.4
3-Methylglutac onyl-C oA
H C N
OOC C H 2 C = C HC OS C oA
6.4.1.4
3-Methylc rotonyl-C oA
H2 C
N
C H3 C H 3 C = C HC OS C oA
1.3.99.10
Is ovaleryl-C oA
(C H 3 ) 2 C HC H 2 C OS C oA
C oenzyme A
+ NH 3 OOC C H-C H 2 C H 2 C H 2 C HC OO + NH 3
2.7.7.15
C holine-P
+ HOC H 2 C H 2 N(C H 3 ) 3
2.7.1.32
C HOL INE
UQH 2
F UMA R A T E
F ADH 2
F e-S C yt.b
1.3.5.1
OOCCH=CHCOO-
+ P OOC C H 2 C H (NH 3 )C OO
A s partyl-P
1 .2
.1 .1
C H 3 C (OH)C H 2 C H 2 O P P
Diphos phomevalonate
S UC C INY L -C oA
6.2.1.4
-OOCCH2CH2CO.SCoA
5.1.99.1 5.4.99.2
1.2.1.16
P s yc hos ine
NHC OR
2.4.1.23
A c yl-C oA
C H2
UQ
4.1.1.33
F AD
II
S UC C INA T E
-OOCCH2CH2COO-
OOC C H 2 C H 2 C HO A s partyl 4.2.1.52 2, 3-DihydroP iperideineN-S uc c inylS emialdehyde dipic olinate 2, 6-dic arboxylate 2-amino-6-oxoS uc c inic pimelate s emialdehyde OH + (C H 3 ) 3 NC H 2 C H(OH)C H 2 C OO
+ OHC C H 2 C H (NH 3 )C OO
HC OOC C
C H2 C H-C OO
H 2C OOC C
C H2 C H-C OO
A M I N O A C I D S
1.3.1.26
2.6.1.17
Glycine
2.3.1.37
UQH 2
C H 3 C -C H 2 C H 2 O P P
2H+
+ H 2 NOC C H 2 C H (NH 3 C OO
C arnitine
+ + (C H 3 ) 3 N(C H 2 ) 3 C H 2 C H(NH 3 )C OO
C erebros ide
C H3
Is opentenyl-P P
(C 5)
1.10.2.2
2UQH 2
5-A minolevulinate
A s paragine
1.14.11.1
2.6.1.19 1.3.99.7
OOC C H 2 C H 2 C H 2 C OS C oA
N 6 -T rimethyl3-OH-lys ine
+ + (C H 3 ) 3 N(C H 2 ) 3 C H 2 C H(NH 3 )C OO
1.14.11.8
N 6 -T rimethyllys ine
LY S INE
.7 5 .1 .1 20 4. 1. 1. 1.5.1.7 - 10
P hytoene
(C 40)
2.5.1.32
Dimethylallyl-P P
(C 5)
2.5.1.1
CH3 C H3
C H 3 C = C HC H 2 O P P
4H+
2.5.1.29
C H 3 C = C HC H 2 C H 2 C = C HC H 2 O P P C H 2O P P
G eranyl-P P
(C 10)
2.5.1.10
2H+
TR A
2-A MINO A C ID
R -C O-C OO
+ R -C H(NH 3 ) C OO
4.1.1.70
G lutaryl-C oA
OOC C H 2 C H 2 C H 2 C OC OO
2-Oxoadipate
+ OOC C H 2 C H 2 C H 2 C H (NH 3 ) C OO
4-A minobutyrate
(G A B A )
H 2 N(C H 2 ) 3 NH (C H 2 ) 4 NH (C H 2 ) 3 NH 2
OOC C H 2 C H 2 C H 2 NH 2
2.6.1.39
+ OHC C H 2 C H 2 C H 2 C H (NH 3 ) C OO
C OO NH C HC H 2 C H 2 C OO
+ C H 2 C H 2 C H 2 C H 2 C H (NH 3 ) C OO
1.5.1.9
S ac c haropine
C H 3 -S C H 2 C H 2 C HNH 2
2-OXO A C ID
2.6.1.-
1eC yt.bH UQ
+ OOC C H 2 C H 2 C H (NH 3 ) C OO
MI
4.
2. 7. 2.
1.
1.
15
S permine
L E G E ND
C arbohydrates A mino A c ids
B ios ynthes is Degradation
NS
NA
G eranyl-geranyl-P P
(C 20)
T IO N
G L UT A MA T E
1.4.1.14
11 P OOC C H C H C H (NH ) C OO 3 2 2
2.5.1.22
H 2 N(C H 2 ) 4 NH (C H 2 ) 3 NH 2
G lutamyl-P
1.2.1.41
S permidine
P hytol
C H3
(C 20)
C H 2 OH
OPP C H2
C yt.c
1.4.1.2
3.5.1.2 6.3.1.2
+ H 2 NOC C H 2 C H 2 C H (NH 3 ) C OO
L ipids
2.5.1.16
H 2 NC H 2 C H 2 C H 2 C H 2 NH 2
F arnes yl-P P
(C 15)
C uA C uA
Heme a
+-
n tra
NO 3 1.6.6.1 1.7.99.4
2H+
F1
NO 2 -
+ NH 4
ATP C O2
G lutamine
+ OHC C H 2 C H 2 C H (NH 3 ) C OO
G lutamic s emialdehyde
2.6.1.13
P utres c ine
C H2 C H2 CH N C HC OO
as
6.3.5.5
P yruvate G lyoxylate
4.1.3.16
OOC C H(OH)C H 2 C OC OO
C H 3 C OC OO
OHC C OO
2H+ C uB Heme a 3
2e-
2H +
AT P
AD
C arbamoyl-P
2
H 2 NC OO P
ATP
+ H 2 NC ONHC H 2 C H 2 C H 2 C H (NH 3 ) C OO
C IT R UL L INE
2.1.3.3
P yrroline-5c arboxylate
4.1.1.17 1.5.99.8 C H2 1.5.1.2
C H2 C HC OO
2.1.3.3
+ H 2 NC H 2 C H 2 C H 2 C H (NH 3 ) C OO
C H2
4-Hydroxy2-oxoglutarate
2.6.1.23
B ios ynthes is
Degradation
F1
H+ H+
OR NIT HINE
F0
H+
NH
6.3.4.5
OOC C HC H 2 C OO N + H 2 NC NHC H 2 C H 2 C H 2 C H (NH 3 ) C OO
P R OL INE
1.14.11.2
HOC H H 2C N H C H2 C HC OO
C OMP A R T ME NT A T ION
T he "B ackbone" of metabolis m involves G LY C OLY S IS in the C Y T OP LAS M, the T C A C Y C LE (mainly) in the Mitochondrial matrix and AT P F OR MAT ION s panning the MIT OC HONDR IAL INNE R ME MB R ANE
H 2 NC ONH 2
2.1.4.1
UR E A
C H2 C H2 C H2 C H2 C H2 C OO -
CH2 H2NCH2C=O
H+ H+
C OO levulinate - OOC
H 2C H 2C
5-A mino-
b- u 1 0 c - s uc
s n it
G lyc ine +
3.5.3.1
3.5.3.6
CH 2 CH 2 N H
+ H 2 NC NHC H 2 C H 2 C H 2 C H (NH 3 ) C OO
NH 2
NO
1.14.13.39
A rgininos uc c inate
4-Hydroxyglutamate
HOC H HC N
1.5.1.12
C H2 C HC OO
TE
D P R OTONS
4.2.1.24
OOC
C H2 C H2 C OO -
A DP
Pi
H+ H+ H+ H+
A R G ININE
4.3.2.1
+ NH
2
HY DR OXY P R OL INE
HN C NH CO CH2 N C H3
3-Hydroxypyrroline5-c arboxylate
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
C OO -
4.1.1.37
Uroporphyrinogen
4.3.1.8 4.2.1.75
H2N
ATP
E ND
Y
A C T IO N
+ NH 2
+ NH 2
E lectron F low
P roton F low
H 2 NC NHC H 2 C OO
G uanidoac etate
2.1.1.2
H 2 NC N(C H 3 )C H 2 C OO
C reatine
2.7.3.2
P - HNC N(C H 3 )C H 2 C OO
1.5.1.2
S mall Numbers ( eg. 2.4.6.7) refer to the IUB MB E nzyme C ommis s ion (E C ) R eference Numbers of E nzymes
P -C reatine
3.5.2.10
P orphobilinogen
E R G O N IC R E
C reatinine
22 nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England and Sigma-A ldrich
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 K orea SIGMA-ALDRICH KOREA Tel: 031-329-9000 Fax: 031-329-9090 M alaysia SIGMA-ALDRICH (M) SDN. BHD Tel: 603-56353321 Fax: 603-56354116 M exico 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 Norw ay 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 A frica 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
Sw eden SIGMA-ALDRICH SWEDEN AB Tel: 020-350510 Fax: 020-352522 Outside Sweden Tel: +46 8 7424200 Outside Sweden Fax: +46 8 7424243 Sw itzerland FLUKA CHEMIE GmbH Swiss Free Call: 0800 80 00 80 Tel: +41 81 755 2828 Fax: +41 81 755 2815 United K ingdom 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/pathw ays