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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 M0181 and M0206

These two reactions have a combined similarity of 0.28


M0181

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Comparison

M0206

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EC 3.11.1.1
phosphonoacetaldehyde hydrolase
Class EC 5.4.2.6
beta-phosphoglucomutase

Image of phosphonoacetaldehyde

Image of water

right arrow

Image of phosphate

Image of acetaldehyde

phosphonoacetaldehyde
C03167
CHEBI:18124
water
C00001
CHEBI:15377
phosphate
C00009
CHEBI:18367
acetaldehyde
C00084
CHEBI:15343
0.33

Image of beta-D-glucose 1-phosphate

right arrow

Image of beta-D-glucose 6-phosphate

beta-D-glucose 1-phosphate
C00663
CHEBI:57684
beta-D-glucose 6-phosphate
C01172
CHEBI:58247

Catalytic CATH Codes

3.40.50.1000
1.10.150.240

Catalytic CATH Codes

3.40.50.1000

Active Site



0.36

Active Site



Catalytic Residues

Type Number Chain Location of Function
Asp 12 A Side Chain
Ala 45 A Main Chain Carbonyl
Met 49 A Side Chain
Lys 53 A Side Chain
His 56 A Side Chain
Arg 160 A Side Chain
0.4

Catalytic Residues

Type Number Chain Location of Function
Asp 1008 A Post-translationally modified residue
Val 1009 A Main Chain Amide
Asp 1010 A Main Chain Amide
Side Chain
Lys 1145 A Side Chain
Ser 1114 A Side Chain
Ala 1115 A Main Chain Amide

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium MG 502 x

Metal Cofactors

Type Het group Number Chain
magnesium MG 2800 _

Reaction occurs across 8 steps

0.2533

Reaction occurs across 4 steps

Step 1
GIF of Reaction Step M0181.stg01

Lys53 attacks the carbonyl carbon of the phosphonoacetaldehyde aldehyde in a nucleophilic addition.
0 Step 1
GIF of Reaction Step M0206.stg01

Asp1010 deprotonates the -CH2-OH group of the substrate sugar, which attacks the phosphate of the phosphorylated Asp1008 in a nucleophilic addition. This produces a pentavalent, covalently attached intermediate.
Step 2
GIF of Reaction Step M0181.stg02

The oxyanion deprotonates the covalently attached Lys53.
0 Step 2
GIF of Reaction Step M0206.stg02

The pentavalent, covalently attached intermediate collapses, eliminating Asp1008 in an un-phosphorylated state.
Step 3
GIF of Reaction Step M0181.stg03

Lys53 initiates an elimination that results in the loss of the alcohol group, which deprotonates a water which in turn deprotonates His56.
0 Step 3
GIF of Reaction Step M0206.stg03

The bisphosphate intermediate rotates in the active site. Asp1008 attacks the C1 phosphate of the intermediate in a nucleophilic addition. This produces a pentavalent, covalently attached intermediate.
Step 4
GIF of Reaction Step M0181.stg04

Asp12 attacks the phosphate of the covalently bound intermediate in a nucleophilic substitution that cleaved the C-P bond and results in a phosphorylated Asp12 and alkylated Lys53
0 Step 4
GIF of Reaction Step M0206.stg04

The pentavalent, covalently attached intermediate collapses, eliminating the final product and Asp1008 in its phosphorylated state.
Step 5
GIF of Reaction Step M0181.stg05

Lys53 initiates a double bond rearrangement that causes the reduction of the C=C in the alkylated intermediate and deprotonates water. The activated water attacks the phosphate in a nucleophilic substitution that releases Asp12 and the phosphate product.
N/A Step 5
No Step with this number present
Step 6
GIF of Reaction Step M0181.stg06

His56 deprotonates water, which deprotonates a second water, which attacks the carbon of the C=N bond in a nucleophilic addition.
N/A Step 6
No Step with this number present
Step 7
GIF of Reaction Step M0181.stg07

Lys53 deprotonates the newly formed alcohol group.
N/A Step 7
No Step with this number present
Step 8
GIF of Reaction Step M0181.stg08

The oxyanion initiates an elimination that releases the acetaldehyde product and regenerates the active site Lys53.
N/A Step 8
No Step with this number present

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