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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 M0106 and M0221

These two reactions have a combined similarity of 0.68


M0106

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Comparison

M0221

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EC 1.2.4.1
pyruvate dehydrogenase (acetyl-transferring)
Class EC 4.1.2.38
benzoin aldolase

Image of [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine

Image of proton

Image of pyruvate

right arrow

Image of carbon dioxide

Image of [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine

[dihydrolipoyllysine-residue acetyltransferase] lipoyllysine
C15972
CHEBI:14919
proton
C00080
CHEBI:24636
pyruvate
C00022
CHEBI:15361
carbon dioxide
C00011
CHEBI:16526
[dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine
C16255
0.28

Image of Benzoin

right arrow

Image of  Benzaldehyde

Benzoin
C01408
CHEBI:17682
2 Benzaldehyde
C00261
CHEBI:17169

Catalytic CATH Codes

3.40.50.970

Catalytic CATH Codes

3.40.50.970
0.0.0.0

Active Site



0.3543

Active Site



Catalytic Residues

Type Number Chain Location of Function
Glu 59 B Side Chain
His 128 B Side Chain
Arg 267 C Side Chain
His 271 C Side Chain
Tyr 281 C Side Chain
0.375

Catalytic Residues

Type Number Chain Location of Function
Glu 50 B Side Chain
His 29 B Side Chain
Gln 113 B Side Chain
Gly 419 A Main Chain Carbonyl

Organic Cofactors

Type Identity Chain
Thiamine diphosphate TDP 1370 C

Organic Cofactors

Type Identity Chain
Thiamine diphosphate TPP 602 A

Metal Cofactors

Type Het group Number Chain
magnesium MG 1368 C

Metal Cofactors

Type Het group Number Chain
magnesium MG 601 A

Reaction occurs across 8 steps

0.8795

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0106.stg01

Glu59 deprotonates the thiamine diphosphate cofactor, which initiates double bond rearrangement that results in the deprotonation of the N=CH-S group, activating the cofactor.
1 Step 1
GIF of Reaction Step M0221.stg01

Glu50B deprotonates the thiamine diphosphate cofactor, which initiates double bond rearrangement that results in the deprotonation of the N=CH-S group, activating the cofactor.
Step 2
GIF of Reaction Step M0106.stg02

The carbanion of thiamine diphosphate initiates a nucleophilic attack on the carbonyl carbon of pyruvate in an addition reaction
0.25 Step 2
GIF of Reaction Step M0221.stg02

The carbanion of thiamine diphosphate attacks the carbonyl carbon of benzoin in a nucleophilic addition. The resulting oxyanion deprotonates water, which in turn deprotonates His29B.
Step 3
GIF of Reaction Step M0106.stg03

The oxyanion formed deprotonates His271C
0 Step 3
GIF of Reaction Step M0221.stg03

His29B deprotonates one of the hydroxyl groups of the bound intermediate, initiating an elimination that productes one of the benzaldehyde products. Thiamine diphosphate acts as an electron sink.
Step 4
GIF of Reaction Step M0106.stg04

The covalently bound intermediate undergoes decarboxylation.
0 Step 4
GIF of Reaction Step M0221.stg04

Thiamine diphosphate initiates a double bond rearrangement, which results in the intermediate being protonated by His29B.
Step 5
GIF of Reaction Step M0106.stg05

The carbanion formed by decarboxylation initiates a nucleophilic attack on the second substrate in an addition reaction with concomitant deprotonation of His128.
0 Step 5
GIF of Reaction Step M0221.stg05

His29B deprotonates the second hydroxyl group of the intermediate, initiating an elimination that results in a reformation of the carbanionic activated cofactor and the second benzaldehyde product.)Substrates=(M0221-I3,2ag0-His29B
Step 6
GIF of Reaction Step M0106.stg06

His271C deprotonates the hydroxyl in an elimination which reforms the carbanionic form of ThDP and produces the second product.
0.2 Step 6
GIF of Reaction Step M0221.stg06

The carbanion of the thiamine diphosphate cofactor deprotonates the adjacent amine, which initiates double bond rearrangement that results in the deprotonation of Glu50B.
Step 7
GIF of Reaction Step M0106.stg07

The carbanion of the thiamine diphosphate cofactor deprotonates the adjacent amine, which initiates double bond rearrangement that results in the deprotonation of Glu59.
N/A Step 7
No Step with this number present
Step 8
GIF of Reaction Step M0106.stg08

His128 deprotonates water in an inferred return step.
N/A Step 8
No Step with this number present

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