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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 M0289 and M0220

These two reactions have a combined similarity of 0.55


M0289

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Comparison

M0220

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EC 2.2.1.6
acetolactate synthase
Class EC 4.1.1.7
benzoylformate decarboxylase

Image of pyruvate

Image of proton

right arrow

Image of carbon dioxide

Image of (S)-2-acetolactate

2 pyruvate
C00022
CHEBI:15361
proton
C00080
CHEBI:15378
CHEBI:24636
carbon dioxide
C00011
CHEBI:16526
(S)-2-acetolactate
C06010
CHEBI:18409
0.33

Image of alpha-Oxo-benzeneacetic acid

right arrow

Image of Carbon dioxide

Image of Benzaldehyde

alpha-Oxo-benzeneacetic acid
C02137
CHEBI:18280
Carbon dioxide
C00011
CHEBI:16526
Benzaldehyde
C00261
CHEBI:17169

Catalytic CATH Codes

3.40.50.970

Catalytic CATH Codes

3.40.50.1220
3.40.50.970

Active Site



0.15984

Active Site



Catalytic Residues

Type Number Chain Location of Function
Glu 139 A Side Chain
Lys 251 A Side Chain
Gln 202 A Side Chain
Met 582 B Side Chain
0.1666

Catalytic Residues

Type Number Chain Location of Function
Glu 47 B Side Chain
Glu 28 B Side Chain
His 70 B Side Chain
Ser 26 B Side Chain
Gly 401 A Main Chain Carbonyl
His 281 A Side Chain

Organic Cofactors

Type Identity Chain
Thiamine diphosphate TPP 1702 B

Organic Cofactors

Type Identity Chain
Thiamine diphosphate TDP 533 A

Metal Cofactors

Type Het group Number Chain
magnesium MG 699 A

Metal Cofactors

Type Het group Number Chain
magnesium MG 529 A

Reaction occurs across 6 steps

0.7391

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0289.stg01

A glutamate residue deprotonates the thiamine diphosphate cofactor at the N1 position. This initiates double bond rearrangement which results in the deprotonation of the N=CH-S group. This activates the cofactor towards electrophilic attack.
1 Step 1
GIF of Reaction Step M0220.stg01

Glu47B 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 M0289.stg02

The carbanion of thiamine diphosphate initiates a nucleophilic attack on the carbonyl carbon of pyruvate in an addition reaction. The conjugated double bond system of the cofactor undergoes rearrangement which results in the deprotonation of the glutamate residue.
0.4 Step 2
GIF of Reaction Step M0220.stg02

The carbanion of thiamine diphosphate attacks the carbonyl carbon of alpha-oxo-benzeneacetic acid in a nucleophilic addition. The formed oxyanion deprotonates His70B
Step 3
GIF of Reaction Step M0289.stg03

The covalently bound pyruvate undergoes decarboxylation.
0.5 Step 3
GIF of Reaction Step M0220.stg03

Carbon dioxide eliminates from the covalently attached aromatic intermediate. Thiamine diphosphate acts as an electron sink.
Step 4
GIF of Reaction Step M0289.stg04

A second pyruvate molecule approaches the cofactor intermediate in a Si orientation and undergoes electrophilic addition at the carbonanion to give the S enantiomeric acetolacty l-ThDP.
0 Step 4
GIF of Reaction Step M0220.stg04

Thiamine diphosphate initiates a double bond rearrangement, which results in the intermediate being protonated by His281A.
Step 5
GIF of Reaction Step M0289.stg05

The acetolacty l-ThDP intermediate undergoes an intramolecular proton transfer with concurrent elimination of S-acetolactate.
0.2 Step 5
GIF of Reaction Step M0220.stg05

His70B deprotonates the hydroxide of the intermediate, which initiates an elimination which results in a reformation of the carbanionic activated cofactor and the benzaldehyde product.
Step 6
GIF of Reaction Step M0289.stg06

The TPP cofactor is regenerated by reprotonation of the C2 position.
0.23 Step 6
GIF of Reaction Step M0220.stg06

The carbanion of the thiamine diphosphate cofactor deprotonates the adjacent amine, which initiates double bond rearrangement that results in the deprotonation of Glu47B. His281A deprotonates water.

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