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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 M0262 and M0253

These two reactions have a combined similarity of 0.30


M0262

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Comparison

M0253

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EC 4.2.3.6
trichodiene synthase
Class EC 2.5.1.10
geranyltranstransferase

Image of 2-trans,6-trans-farnesyl diphosphate

right arrow

Image of trichodiene

Image of diphosphate

2-trans,6-trans-farnesyl diphosphate
C00448
CHEBI:175763
trichodiene
C01860
CHEBI:15861
diphosphate
C00013
CHEBI:33019
0.52

Image of isopentenyl diphosphate

Image of geranyl diphosphate

right arrow

Image of trans,trans-farnesyl diphosphate

Image of diphosphate

isopentenyl diphosphate
C00129
CHEBI:128769
geranyl diphosphate
C00341
CHEBI:58057
trans,trans-farnesyl diphosphate
C00448
CHEBI:17407
diphosphate
C00013
CHEBI:33019

Catalytic CATH Codes

1.10.600.10

Catalytic CATH Codes

1.10.600.10

Active Site



0.08051

Active Site



Catalytic Residues

Type Number Chain Location of Function
Tyr 93 B Side Chain
Arg 182 B Side Chain
Lys 232 B Side Chain
Arg 304 B Side Chain
Tyr 305 B Side Chain
Thr 96 B Side Chain
Leu 97 B Side Chain
Asp 100 B Side Chain
0.0769

Catalytic Residues

Type Number Chain Location of Function
Phe 112 A Side Chain
Lys 214 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium MG 701 B
magnesium MG 702 B
magnesium MG 703 B

Metal Cofactors

Type Het group Number Chain
magnesium MG 402 A
magnesium MG 403 A
magnesium No Available PDB Information

Reaction occurs across 6 steps

0.3513

Reaction occurs across 3 steps

Step 1
GIF of Reaction Step M0262.stg01

The binding of the substrate causes a conformation change in the active site, which promotes the elimination of the pyrophosphate.
0.33 Step 1
GIF of Reaction Step M0253.stg01

The substrate undergoes heterolysis. The diphosphate product remains associated with the active site, and the cabocation is delocalised over the three terminal carbon atoms of the intermediate.
Step 2
GIF of Reaction Step M0262.stg02

The pyrophosphate attacks the C3 cationic carbon in a nucleophilic addition reaction.
0 Step 2
GIF of Reaction Step M0253.stg02

The double bond of isopentenyl diphosphate adds to the terminal carbocation in an electrophilic addition.
Step 3
GIF of Reaction Step M0262.stg03

Intramolecular elimination of the pyrophosphate.
0.2 Step 3
GIF of Reaction Step M0253.stg03

The diphosphate formed in the initial heterolysis deprotonates the carbon adjacent to the newly formed carbocation, forming a new double bond in the trans,trans-farnesyl diphosphate product.
Step 4
GIF of Reaction Step M0262.stg04

Intramolecular electrophilic addition across the C1-C6 bond to form the six-membered ring.
N/A Step 4
No Step with this number present
Step 5
GIF of Reaction Step M0262.stg05

Intramolecular electrophilic addition across the C10-C7 bond to form the five-membered ring.
N/A Step 5
No Step with this number present
Step 6
GIF of Reaction Step M0262.stg06

The Pyrophosphate deprotonates the substrate, which initiates the first methyl migration, followed by a second methyl migration and finally a 1,4-hydride shift.
N/A Step 6
No Step with this number present

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