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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 M0259

These two reactions have a combined similarity of 0.44


M0262

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Comparison

M0259

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EC 4.2.3.6
trichodiene synthase
Class EC 5.5.1.8
bornyl diphosphate synthase

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
0.5

Image of geranyl diphosphate

right arrow

Image of (+)-bornyl diphosphate

geranyl diphosphate
C00341
CHEBI:58057
(+)-bornyl diphosphate
C03190
CHEBI:57293

Catalytic CATH Codes

1.10.600.10

Catalytic CATH Codes

1.10.600.10

Active Site



0.0113

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

Catalytic Residues

Type Number Chain Location of Function
Trp 323 A Side Chain
Phe 578 A Side Chain
Ile 344 A Side Chain
Val 452 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 701 A
magnesium MG 702 A
magnesium MG 703 A

Reaction occurs across 6 steps

0.6086

Reaction occurs across 6 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 M0259.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.
0.33 Step 2
GIF of Reaction Step M0259.stg02

The diphosphate initiates nucleophilic attack at the C4 carbon, which causes double bond rearrangement and the formation of the linalyl diphosphate intermediate.
Step 3
GIF of Reaction Step M0262.stg03

Intramolecular elimination of the pyrophosphate.
0.33 Step 3
GIF of Reaction Step M0259.stg03

The linalyl diphosphate 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 4
GIF of Reaction Step M0262.stg04

Intramolecular electrophilic addition across the C1-C6 bond to form the six-membered ring.
0.6 Step 4
GIF of Reaction Step M0259.stg04

The terminal double bond adds to the newly formed carbocation in an intramolecular electrophilic addition resulting in a cyclic intermediate.
Step 5
GIF of Reaction Step M0262.stg05

Intramolecular electrophilic addition across the C10-C7 bond to form the five-membered ring.
1 Step 5
GIF of Reaction Step M0259.stg05

The remaining double bond adds to the newly formed carbocation in an intramolecular electrophilic addition resulting in a bicyclic intermediate.
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.
0 Step 6
GIF of Reaction Step M0259.stg06

The diphosphate initiates nucleophilic attack at the carbocation, forming the final product.

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