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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 M0107 and M0103

These two reactions have a combined similarity of 0.26


M0107

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Comparison

M0103

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EC 1.2.99.2
carbon-monoxide dehydrogenase (acceptor)
Sub-Class EC 1.1.3.38
vanillyl-alcohol oxidase

Image of acceptor

Image of carbon monoxide

Image of water

right arrow

Image of proton

Image of carbon dioxide

Image of reduced acceptor

acceptor
C00028
CHEBI:15339
carbon monoxide
C00237
CHEBI:17245
water
C00001
CHEBI:15377
2 proton
C00080
CHEBI:24636
carbon dioxide
C00011
CHEBI:16526
reduced acceptor
C00030
CHEBI:17499
0.27

Image of oxygen

Image of water

Image of 4-(methoxymethyl)phenol

right arrow

Image of 4-hydroxybenzaldehyde

Image of hydrogen peroxide

Image of methanol

oxygen
C00007
CHEBI:15379
water
C00001
CHEBI:15377
4-(methoxymethyl)phenol
X00032
4-hydroxybenzaldehyde
C00633
CHEBI:17597
hydrogen peroxide
C00027
CHEBI:16240
methanol
C00132
CHEBI:17790

Catalytic CATH Codes

3.30.365.10
0.0.0.0

Catalytic CATH Codes

3.30.43.10
3.30.465.10
3.40.462.10

Active Site



0

Active Site



Catalytic Residues

Type Number Chain Location of Function
Cys 388 B Side Chain
Glu 763 B Side Chain
0

Catalytic Residues

Type Number Chain Location of Function
Tyr 108 A Side Chain
Asp 170 A Side Chain
Tyr 503 A Side Chain
Arg 504 A Side Chain
His 422 A Side Chain

Organic Cofactors

Type Identity Chain
FAD FAD 3932

Organic Cofactors

Type Identity Chain
FAD FAD 600 A

Metal Cofactors

Type Het group Number Chain
iron FES 3907 x
iron FES 3908 x
copper CUB 3921 x
molybdenum CUB 3921 x

Metal Cofactors

No Associated Metal Cofactors

Reaction occurs across 8 steps

0.3587

Reaction occurs across 8 steps

Step 1
GIF of Reaction Step M0107.stg01

Carbon monoxide coordinates to the Cu(I) centre.
0 Step 1
GIF of Reaction Step M0103.stg01

Asp170 deprotonates the 4-OH of the substrate, forming a pheonlate.
Step 2
GIF of Reaction Step M0107.stg02

The Carbanion of carbon monoxide initiates a nucleophilic attack on the oxo group coordinated to the Mo(VI) centre, which results in the reduction of the molybdenum to Mo(IV). The C#O triple bond reduces in order to C=O.
0 Step 2
GIF of Reaction Step M0103.stg02

The oxyanion collapses with double bond rearrangement, eliminating a hydride from the 1-methoxy carbon, which is added to FAD.
Step 3
GIF of Reaction Step M0107.stg03

The sulfur dianion bridging the Mo(IV) and Cu(I) centres initiates a nucleophilic attack on the carbocation in a substitution reaction that displaces the carbon from the Cu(I) centre.
0 Step 3
GIF of Reaction Step M0103.stg03

The FAD undergoes double bond rearrangement which causes a single electron to be transferred to a dioxygen molecule.
Step 4
GIF of Reaction Step M0107.stg04

The carbonyl oxygen initiates a nucleophilic attack on the Cu(I) centre in a substitution reaction that displaces the bridging sulfur ligand from the Cu(I) centre.
0 Step 4
GIF of Reaction Step M0103.stg04

The dioxygen molecule undergoes a homolytic reaction in which it colligates to FAD, with concomitant deprotonation of Asp170.
Step 5
GIF of Reaction Step M0107.stg05

Water initiates a nucleophilic attack on the Mo(IV) centre, displacing the negatively charged oxygen of the carboxylate group in a substitution reaction, which initiates an elimination of the sulfur group, to reform the bridging sulfur dianion and the formation of carbon dioxide, which decoordinates from the metal centre.
0 Step 5
GIF of Reaction Step M0103.stg05

The peroxo group deprotonates FAD, which initiates the elimination of hydrogen peroxide.
Step 6
GIF of Reaction Step M0107.stg06

Glu763 deprotonates water, initiating a single electron transfer from the Mo(IV) centre, through two iron-sulfur clusters to FAD, and thence to an external electron acceptor.
0.5 Step 6
GIF of Reaction Step M0103.stg06

Asp170 deprotonates water, which initiates a nucleophilic attack on the methoxy group, in a substitution reaction which eliminates methoxide.
Step 7
GIF of Reaction Step M0107.stg07

Water deprotonates Glu763, which then deprotonates the Mo(V) bound hydroxide, initiating the second single electron transfer, through two iron-sulfur clusters to FAD, and thence to an external electron acceptor. This regenerates the cofactor.
0.37 Step 7
GIF of Reaction Step M0103.stg07

The methoxide deprotonates the alcohol group, initiating double bond rearrangement, which re-forms the phenolate moiety.
Step 8
GIF of Reaction Step M0107.stg08

Water deprotonates Glu763 in an inferred return step.
1 Step 8
GIF of Reaction Step M0103.stg08

The pheonlate deprotonates Asp170.

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