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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 M0141 and M0107

These two reactions have a combined similarity of 0.19


M0141

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Comparison

M0107

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EC 1.17.99.1
4-cresol dehydrogenase (hydroxylating)
Sub-Class EC 1.2.99.2
carbon-monoxide dehydrogenase (acceptor)

Image of acceptor

Image of 4-cresol

Image of water

right arrow

Image of proton

Image of 4-hydroxybenzaldehyde

Image of reduced acceptor

2 acceptor
C00028
CHEBI:17654
4-cresol
C01468
CHEBI:17847
water
C00001
CHEBI:15377
4 proton
C00080
CHEBI:24636
4-hydroxybenzaldehyde
C00633
CHEBI:17597
2 reduced acceptor
C00030
0.5

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

Catalytic CATH Codes

3.40.462.10
3.30.465.10
1.10.45.10
1.10.760.10

Catalytic CATH Codes

3.30.365.10
0.0.0.0

Active Site



0.108

Active Site



Catalytic Residues

Type Number Chain Location of Function
Asp 167 A Side Chain
Glu 177 A Side Chain
Glu 286 A Side Chain
Tyr 367 A Side Chain
Glu 380 A Side Chain
Tyr 384 A Side Chain
His 436 A Side Chain
Tyr 473 A Side Chain
Arg 474 A Side Chain
Arg 512 A Side Chain
Ala 649 C Main Chain Carbonyl
Met 650 C Side Chain
0.12

Catalytic Residues

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

Organic Cofactors

Type Identity Chain
FAD FAD 599 A

Organic Cofactors

Type Identity Chain
FAD FAD 3932

Metal Cofactors

Type Het group Number Chain
iron HEM 699 C

Metal Cofactors

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

Reaction occurs across 11 steps

0.1756

Reaction occurs across 8 steps

Step 1
GIF of Reaction Step M0141.stg01

Proton relay from bulk solvent through Glu177, His436 and Tyr473 to the substrate 4-cresol, resulting in a hydride transfer from the 4-cresol to the cofactor FAD599.
0 Step 1
GIF of Reaction Step M0107.stg01

Carbon monoxide coordinates to the Cu(I) centre.
Step 2
GIF of Reaction Step M0141.stg02

Glu380 deprotonates water, activating it for a nucleophilic addition to the creosol intermediate. This intermediate is re-protonated via the proton relay chain through Tyr473, His436 and Glu177 to bulk solvent.
0.01 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.
Step 3
GIF of Reaction Step M0141.stg03

Glu380 is deprotonated through the proton relay chain of Tyr367, water, Glu286 and bulk solvent.
0 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.
Step 4
GIF of Reaction Step M0141.stg04

FAD599 loses a single electron through the Tyr384 covalently attached to the FAD, the main chain carbonyl of Ala649C, side chain of Met650C and the heme cofactor to the external electron acceptor.
0 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.
Step 5
GIF of Reaction Step M0141.stg05

Glu380 deprotonates the activated FAD599, resulting in the second electron transfer through the Tyr384 covalently attached to the FAD, the main chain carbonyl of Ala649C, side chain of Met650C and the heme cofactor to the external electron acceptor.
0 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.
Step 6
GIF of Reaction Step M0141.stg06

Glu380 is deprotonated through the proton relay chain of Tyr367, water, Glu286 and bulk solvent.
0.28 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.
Step 7
GIF of Reaction Step M0141.stg07

Glu380 deprotonates the intermediate, causing a reduction of the primary alcohol to an aldehyde with concomitant transfer of a hydride to FAD599.
0.37 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.
Step 8
GIF of Reaction Step M0141.stg08

Glu380 is deprotonated through the proton relay chain of Tyr367, water, Glu286 and bulk solvent.
0.28 Step 8
GIF of Reaction Step M0107.stg08

Water deprotonates Glu763 in an inferred return step.
Step 9
GIF of Reaction Step M0141.stg09

FAD599 loses a single electron through the Tyr384 covalently attached to the FAD, the main chain carbonyl of Ala649C, side chain of Met650C and the heme cofactor to the external electron acceptor.
N/A Step 9
No Step with this number present
Step 10
GIF of Reaction Step M0141.stg10

Glu380 deprotonates the activated FAD599, resulting in the second electron transfer through the Tyr384 covalently attached to the FAD, the main chain carbonyl of Ala649C, side chain of Met650C and the heme cofactor to the external electron acceptor.
N/A Step 10
No Step with this number present
Step 11
GIF of Reaction Step M0141.stg11

Glu380 is deprotonated through the proton relay chain of Tyr367, water, Glu286 and bulk solvent.
N/A Step 11
No Step with this number present

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