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4.2.3.6: trichodiene synthase

This is an abbreviated version!
For detailed information about trichodiene synthase, go to the full flat file.

Word Map on EC 4.2.3.6

Reaction

(2E,6E)-farnesyl diphosphate
=
trichodiene
 +
diphosphate

Synonyms

EC 4.1.99.6, sesquiterpene cyclase, synthase, trichodiene, TDN synthase, trans,trans-farnesyl-diphosphate sesquiterpenoid-lyase, tri5, trichodiene synthase, trichodiene synthetase

ECTree

     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.3 Acting on phosphates
                4.2.3.6 trichodiene synthase

Inhibitors

Inhibitors on EC 4.2.3.6 - trichodiene synthase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(7R)-(E)-6,7-dihydrofarnesyl diphosphate
-
-
(7S)-(E)-6,7-dihydrofarnesyl diphosphate
-
modestly competitive
1-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]proline
-
40.3% inhibition at 0.0187 mM
10-cyclopropylidene farnesyl diphosphate
-
mechanism-based inhibitor
10-fluorofarnesyl diphosphate
-
-
2-([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)-N-[2-(4-hydroxyphenyl)ethyl]acetamide
-
45% inhibition at 0.0187 mM
3-(1H-indol-2-yl)-N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]alanine
-
67.8% inhibition at 0.0187 mM
3-phenyl-4-[2-([(Z)-[(3Z)-11,17,21-trihydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamido]butanoic acid
-
26.7% inhibition at 0.0187 mM
4-[2-([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamido]-3-phenylbutanoic acid
-
12.2% inhibition at 0.0187 mM
benzyl triethylammonium cation
-
BTAC alone does not inhibit the trichodiene synthase, 5-30 microM acts as a competitive inhibitor in the presence of 5-20 microM PPi
beta-hydroxy-N-[([(Z)-[(3Z,17alpha)-17-hydroxypregn-4-en-20-yn-3-ylidene]amino]oxy)acetyl]phenylalanine
-
21.1% inhibition at 0.0187 mM
diphosphate
-
PPi
ethyl beta-hydroxy-N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]phenylalaninate
-
25.3% inhibition at 0.0187 mM
farnesyl diphosphate analogs
methyl 1-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]prolinate
-
70.5% inhibition at 0.0187 mM
methyl N-[([(Z)-[(3Z)-11,17,21-trihydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]phenylalaninate
-
21.6% inhibition at 0.0187 mM
methyl N-[([(Z)-[(3Z)-11,17,21-trihydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]tyrosinate
-
22.6% inhibition at 0.0187 mM
methyl N-[([(Z)-[(3Z)-17-hydroxyandrost-4-en-3-ylidene]amino]oxy)acetyl]phenylalaninate
-
53.2% inhibition at 0.0187 mM
methyl N-[([(Z)-[(3Z)-17-hydroxypregn-4-en-20-yn-3-ylidene]amino]oxy)acetyl]phenylalaninate
-
66.3% inhibition at 0.0187 mM
Mn2+
-
0.01 mM, can partially replace Mg2+, inhibition at higher concentration
N-[(3,4-dihydroxyphenyl)methyl]-2-([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamide
-
70.6% inhibition at 0.0187 mM
N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]-3-(1H-indol-2-yl)alanine
-
61.8% inhibition at 0.0187 mM
N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]glycine
-
59.5% inhibition at 0.0187 mM
N-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]valine
-
49% inhibition at 0.0187 mM
N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]isoleucine
-
54.8% inhibition at 0.0187 mM
N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]phenylalanine
-
39% inhibition at 0.0187 mM
N-[([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]serine
-
44.5% inhibition at 0.0187 mM
N-[2-(4-hydroxyphenyl)ethyl]-2-([(Z)-[(3Z)-20-oxopregn-4-en-3-ylidene]amino]oxy)acetamide
-
58.4% inhibition at 0.0187 mM
N2-[([(Z)-[(3Z)-17-hydroxy-20-oxopregn-4-en-3-ylidene]amino]oxy)acetyl]asparagine
-
54.3% inhibition at 0.0187 mM
additional information
-
identification of active site residues by site-directed mutagenesis
-