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The two reactions compared are done so using a Tanimoto similarity score (for more information, please see the MACiE FAQ) for the bond changes only. The score maay range from 0 to 1 where 1 indicates that the two reactions are identical at the bond change level and 0 indicates that there are no bond changes in common.


Key

1.0-0.9 0.9-0.8 0.8-0.7 0.7-0.6 0.6-0.5 0.5-0.4 0.4-0.3 0.3-0.2 0.2-0.1 0.1-0.0 =0

Results for Comparison of M0222 and M0108

These two reactions have a combined similarity of 0.21


M0222

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Comparison

M0108

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EC 4.1.2.13
fructose-bisphosphate aldolase (Class I)
Class EC 1.3.1.34
2,4-dienoyl-CoA reductase (NADPH)

Image of D-glyceraldehyde 3- phosphate

Image of glycerone phosphate

right arrow

Image of D-fructose 1,6-bisphosphate

D-glyceraldehyde 3- phosphate
C00118
CHEBI:59776
glycerone phosphate
C00111
CHEBI:57642
D-fructose 1,6-bisphosphate
C00354
CHEBI:49299
0.05

Image of NADPH

Image of trans,trans-2,3,4,5-tetradehydroacyl-CoA

Image of proton

right arrow

Image of NADP

Image of trans-2,3-didehydroacyl-CoA

NADPH
C00005
CHEBI:16474
trans,trans-2,3,4,5-tetradehydroacyl-CoA
C04512
CHEBI:58036
proton
C00080
CHEBI:24636
NADP
C00006
CHEBI:18009
trans-2,3-didehydroacyl-CoA
C00658
CHEBI:58856

Catalytic CATH Codes

3.20.20.70

Catalytic CATH Codes

3.20.20.70

Active Site



0.22003

Active Site



Catalytic Residues

Type Number Chain Location of Function
Lys 146 A Side Chain
Ser 300 A Side Chain
Tyr 363 A Side Chain
Asp 33 A Side Chain
Lys 229 A Side Chain
Glu 187 A Side Chain
Glu 189 A Side Chain
0.2307

Catalytic Residues

Type Number Chain Location of Function
Glu 164 A Side Chain
Tyr 166 A Side Chain
Arg 214 A Side Chain
His 252 A Side Chain
Gln 339 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

Type Identity Chain
FAD FAD 701
FMN FMN 702

Metal Cofactors

No Associated Metal Cofactors

Metal Cofactors

Type Het group Number Chain
iron FS4 700 A

Reaction occurs across 10 steps

0.2439

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0222.stg01

Lys229 attacks the carbonyl carbon of D-glyceraldehyde 3- phosphate in a nucleophilic addition.
0 Step 1
GIF of Reaction Step M0108.stg01

NADP eliminates a hydride ion, which is added to FAD.
Step 2
GIF of Reaction Step M0222.stg02

The oxyanion formed deprotonates the bound Lys229.
0.1 Step 2
GIF of Reaction Step M0108.stg02

FAD transfers a single electron, through Gln339 and an iron-sulfur cluster, to FMN, which deprotonates water.
Step 3
GIF of Reaction Step M0222.stg03

Lys229 initiates an elimination of water, which gains an extra proton from Glu187.
0.28 Step 3
GIF of Reaction Step M0108.stg03

Water deprotonates FAD, which initiates a second single electron transfer, through Gln339 and an iron-sulfur cluster, to FMN. This regenerates the FAD cofactor, and produces fully reduced FMN.
Step 4
GIF of Reaction Step M0222.stg04

The phosphate of the bound intermediate deprotonates water, which in turn deprotonates Tyr363.
0 Step 4
GIF of Reaction Step M0108.stg04

FMN eliminates a hydride ion, which is added to the C5 of the substrate. This initiates double bond rearrangement, resulting in an oxyanion on the C1.
Step 5
GIF of Reaction Step M0222.stg05

Tyr363 deprotonates the C1-H of the bound intermediate, initiating a double bond rearrangement that leaves Lys229 with a lone pair of electrons.
0.09 Step 5
GIF of Reaction Step M0108.stg05

The oxyanion collapses, initiating double bond rearrangement, the C4 of the intermediate deprotonates Tyr166.
Step 6
GIF of Reaction Step M0222.stg06

Glu187 deprotonates water, which deprotonates a second water which deprotonates the phosphate of the bound intermediate.
0.42 Step 6
GIF of Reaction Step M0108.stg06

Tyr166 deprotonates water in an inferred return step.
Step 7
GIF of Reaction Step M0222.stg07

Glycerone phosphate binds, displacing one of the water molecules. Lys229 initiates a nucleophilic addition of the bound intermediate to the glycerone phosphate. The formed oxyanion deprotonates Glu187.
N/A Step 7
No Step with this number present
Step 8
GIF of Reaction Step M0222.stg08

Glu187 deprotonates water, which attacks the imine carbon of the covalenlty bound intermediate in a nucleophilic addition.
N/A Step 8
No Step with this number present
Step 9
GIF of Reaction Step M0222.stg09

Lys229 deprotonates the formed hydroxyl group, which initiates an elimination of the linear form of D-fructose 1,6-bisphosphate and neutral Lys229.
N/A Step 9
No Step with this number present
Step 10
GIF of Reaction Step M0222.stg10

Phosphate deprotonates hydroxyl, and the carbonyl oxygen re-protonates from Lys229, which in turn re-protonates from the phosphate, thus catalysing the ring closure of D-fructose 1,6-bisphosphate.
N/A Step 10
No Step with this number present

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