BRENDA - Enzyme Database
show all sequences of 4.2.3.16

Irreversible inactivation of monoterpene cyclases by a mechanism-based inhibitor

Croteau, R.; Alonso, W.R.; Koepp, A.E.; Shim, J.H.; Cane, D.E.; Arch. Biochem. Biophys. 307, 397-404 (1993)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
6-cyclopropylidene-(3E)-methyl-hex-2-en-1-yl diphosphate
Ki: 0.0003 mM, irreversible covalent modification
Mentha sp.
diethyl dicarbonate
-
Mentha sp.
p-hydroxymercuribenzoate
-
Mentha sp.
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
geranyl diphosphate
Mentha sp.
-
(-)-(4S)-limonene + diphosphate
-
Mentha sp.
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Mentha sp.
-
M. spicata
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
leaf
glandular trichome secretory cells
Mentha sp.
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
geranyl diphosphate
-
3768
Mentha sp.
(-)-(4S)-limonene + diphosphate
-
3768
Mentha sp.
?
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.0003
-
6-cyclopropylidene-(3E)-methyl-hex-2-en-1-yl diphosphate
irreversible covalent modification
Mentha sp.
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
6-cyclopropylidene-(3E)-methyl-hex-2-en-1-yl diphosphate
Ki: 0.0003 mM, irreversible covalent modification
Mentha sp.
diethyl dicarbonate
-
Mentha sp.
p-hydroxymercuribenzoate
-
Mentha sp.
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.0003
-
6-cyclopropylidene-(3E)-methyl-hex-2-en-1-yl diphosphate
irreversible covalent modification
Mentha sp.
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
geranyl diphosphate
Mentha sp.
-
(-)-(4S)-limonene + diphosphate
-
Mentha sp.
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
leaf
glandular trichome secretory cells
Mentha sp.
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
geranyl diphosphate
-
3768
Mentha sp.
(-)-(4S)-limonene + diphosphate
-
3768
Mentha sp.
?
Other publictions for EC 4.2.3.16
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
746187
Fukushima
High-throughput sequencing an ...
Perilla frutescens var. crispa
PLoS ONE
10
e0129154
2015
-
-
-
-
-
-
-
-
-
-
-
1
-
3
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
1
1
1
1
-
-
730319
Alonso-Gutierrez
Metabolic engineering of Esche ...
Mentha spicata
Metab. Eng.
19
33-41
2013
-
1
1
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
706153
Ohara
Monoterpene engineering in a w ...
Perilla frutescens
Plant Biotechnol. J.
8
28-37
2010
-
-
1
-
-
-
-
-
-
-
-
-
-
6
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
712853
Dolzhenko
UV-B modulates the interplay b ...
Mentha x piperita
J. Photochem. Photobiol. B Biol.
100
67-75
2010
-
1
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
693992
Munoz-Bertomeu
Expression of spearmint limone ...
Mentha spicata
Metab. Eng.
10
166-177
2008
-
2
1
-
-
-
-
-
1
-
-
2
-
3
-
-
-
-
-
6
1
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
2
1
-
-
-
-
-
-
-
-
1
-
-
2
-
-
-
-
-
6
1
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
682075
Gunnewich
-
Functional expression and char ...
Cannabis sativa
Nat. Prod. Commun.
2
223-232
2007
-
-
-
-
-
-
-
1
-
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
1
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
682572
Hyatt
Structure of limonene synthase ...
Mentha spicata
Proc. Natl. Acad. Sci. USA
104
5360-5365
2007
-
-
-
1
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
682398
Byun-McKay
Wound-induced terpene synthase ...
Picea sitchensis
Plant Physiol.
140
1009-1021
2006
-
-
-
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
649494
Katoh S.;Hyatt D.;Croteau R.
Altering product outcome in Ab ...
Abies grandis
Arch. Biochem. Biophys.
425
65-76
2004
-
-
1
-
1
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
663127
Martin
Functional characterization of ...
Picea abies
Plant Physiol.
135
1908-1927
2004
-
-
1
-
-
-
-
-
-
-
-
-
-
5
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
652953
Schwab W.;Williams DC
-
Mechanism of monoterpene cycli ...
Mentha spicata
J. Mol. Catal. B
19
415-421
2002
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
639023
Maruyama
Molecular cloning, functional ...
Agastache rugosa
Biol. Pharm. Bull.
24
373-377
2001
-
-
1
-
-
-
-
-
-
-
1
-
-
3
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
649447
Schwab
Mechanism of monoterpene cycli ...
Mentha spicata
Arch. Biochem. Biophys.
392
123-136
2001
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210773
Turner
Limonene synthase, the enzyme ...
Mentha sp.
Plant Physiol.
120
879-886
1999
-
-
-
-
-
-
-
-
2
-
1
1
-
3
-
-
1
-
-
3
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
1
1
-
-
-
1
-
3
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
701897
Bohlmann
cDNA cloning, characterization ...
Abies grandis
Arch. Biochem. Biophys.
368
232-243
1999
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210753
Bohlmann
Monoterpene synthases from gra ...
Abies grandis
J. Biol. Chem.
272
21784-21792
1997
-
-
1
-
-
-
-
-
-
3
1
1
-
5
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
3
1
1
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210766
Yuba
cDNA cloning, characterization ...
Perilla frutescens
Arch. Biochem. Biophys.
332
280-287
1996
-
-
1
-
-
-
-
-
-
-
-
1
-
7
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210772
Adam
Partial purification and chara ...
Ricciocarpos natans
Arch. Biochem. Biophys.
332
352-356
1996
-
-
-
-
-
-
-
1
-
2
1
1
-
4
-
-
1
-
-
-
-
-
1
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
2
1
1
-
-
-
1
-
-
-
-
1
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
3768
Croteau
Irreversible inactivation of m ...
Mentha sp.
Arch. Biochem. Biophys.
307
397-404
1993
-
-
-
-
-
-
3
-
-
-
-
1
-
4
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
3
1
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210765
Colby
4S-limonene synthase from the ...
Mentha sp.
J. Biol. Chem.
268
23016-23024
1993
-
-
1
-
-
-
-
-
-
1
2
1
-
6
-
-
1
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
1
2
1
-
-
-
1
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210770
Alonso
Production and characterizatio ...
Mentha sp.
Arch. Biochem. Biophys.
301
58-63
1993
-
-
-
-
-
-
-
-
-
-
1
1
-
9
-
-
1
-
-
5
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
1
-
5
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210767
Alonso
Purification of 4S-limonene sy ...
Mentha sp.
J. Biol. Chem.
267
7582-7587
1992
-
-
-
-
-
-
-
-
-
-
1
1
-
1
-
-
1
-
-
1
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
1
-
1
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
210768
Rajaonarivony
Characterization and mechanism ...
Mentha sp.
Arch. Biochem. Biophys.
296
49-57
1992
1
-
-
-
-
1
7
4
-
3
-
1
-
3
-
-
1
-
-
7
-
1
4
-
-
-
-
-
1
1
-
-
2
-
-
1
-
-
-
-
-
1
-
7
2
4
-
3
-
1
-
-
-
1
-
7
-
1
4
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
586994
Rajaonarivony
Evidence for an essential hist ...
Mentha sp.
Arch. Biochem. Biophys.
299
77-82
1992
-
-
-
-
-
-
3
-
-
1
-
1
-
2
-
-
-
-
-
3
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
1
-
1
-
-
-
-
-
3
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-