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EC Tree
IUBMB Comments Forms the first step of carvone biosynthesis in caraway. The enzyme from Carum carvi (caraway) seeds requires a divalent metal ion (preferably Mn2+) for catalysis. This enzyme occurs in Citrus, Carum (caraway) and Anethum (dill); (-)-limonene, however, is made in the fir, Abies, and mint, Mentha, by EC 4.2.3.16, (4S)-limonene synthase.
The enzyme appears in viruses and cellular organisms
Synonyms
d-limonene synthase, (+)-limonene synthase, citmtse1, cl(+)lims2, lalims, (+)-ls, cl(+)lims1,
more
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(+)-limonene synthase
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(+)-limonene synthase
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(+)-limonene synthase
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(+)-LS
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CitMTSE1
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Cl(+)LIMS1
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-
-
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d-limonene synthase
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d-limonene synthase
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d-limonene synthase
Nepeta tenuifolia
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limonene synthase
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limonene synthase
Nepeta tenuifolia
-
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geranyl diphosphate = (R)-limonene + diphosphate
geranyl diphosphate = (R)-limonene + diphosphate
requires a divalent metal ion (preferably Mn2+) for catalysis
geranyl diphosphate = (R)-limonene + diphosphate
forms the first step of carvone biosynthesis in caraway
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geranyl diphosphate = (R)-limonene + diphosphate
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cyclization
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-
cyclization
Nepeta tenuifolia
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geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-(4R)-limonene-forming]
Forms the first step of carvone biosynthesis in caraway. The enzyme from Carum carvi (caraway) seeds requires a divalent metal ion (preferably Mn2+) for catalysis. This enzyme occurs in Citrus, Carum (caraway) and Anethum (dill); (-)-limonene, however, is made in the fir, Abies, and mint, Mentha, by EC 4.2.3.16, (4S)-limonene synthase.
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2-fluorogeranyl diphosphate
?
-
-
-
-
?
2-fluoroneryl diphosphate
?
-
-
-
-
?
geranyl diphosphate
(+)-(4R)-limonene + diphosphate
-
-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
geranyl diphosphate
(1R,4S)-(+)-camphene + diphosphate
-
-
-
?
geranyl diphosphate
(1R,5R)-(+)-alpha-pinene + diphosphate
-
-
-
?
geranyl diphosphate
(4R)-limonene + diphosphate
geranyl diphosphate
(D)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
geranyl diphosphate
(S)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
alpha-phellandrene + diphosphate
-
-
-
?
geranyl diphosphate
beta-myrcene + diphosphate
-
-
-
?
geranyl diphosphate
D-limonene + diphosphate
Nepeta tenuifolia
single step in plants
D-limonene shows cancer preventative and cancer therapeutic activities in vitro and in vivo, its modulates apoptosis-related genes and proteins in cultured cells
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?
geranyl diphosphate
terpinolene + diphosphate
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-
-
?
additional information
?
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geranyl diphosphate
(+)-(R)-limonene + diphosphate
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-
-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
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-
high stereoselectivity, 98.4% of (+)-product
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geranyl diphosphate
(+)-(R)-limonene + diphosphate
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-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
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product is exclusively R-(+)-limonene
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
Nepeta tenuifolia
-
-
-
?
geranyl diphosphate
(4R)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
(4R)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
-
products are 39% (R)-limonene, 22% terpinolene, 16% (1R,5S)-camphene, 14% (1R,5R)-(+)-alpha-pinene, 8% betamyrcene and traces of alpha-phellandrene. Product pattern changes markedly to 46% limonene, 9% terpinolene, 23% alpha-pinene, 5% beta-myrcene and 4% alpha-phellandrene, when Mn2+ is supplied instead of Mg2+
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?
additional information
?
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no substrates: farnesyl diphosphate, geranylgeranyl diphosphate
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?
additional information
?
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no substrates: farnesyl diphosphate, geranylgeranyl diphosphate
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?
additional information
?
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Nepeta tenuifolia
a concomitant increase in the level of apoptosis-related protein B-cell lymphoma protein 2 and decreases in the levels of Bcl-2 antagonist of cell death and phosphorylated c-Jun N-terminal kinase are observed in limonene-producing cells
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?
additional information
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Nepeta tenuifolia
limonene can be synthesized in animal cells using their own mevalonate pathway and limonene-producing cells may provide a new system for the elucidation of limonene function
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?
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geranyl diphosphate
(+)-(4R)-limonene + diphosphate
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-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
geranyl diphosphate
(D)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
geranyl diphosphate
(S)-limonene + diphosphate
-
-
-
-
?
geranyl diphosphate
D-limonene + diphosphate
Nepeta tenuifolia
single step in plants
D-limonene shows cancer preventative and cancer therapeutic activities in vitro and in vivo, its modulates apoptosis-related genes and proteins in cultured cells
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?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
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-
-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
-
-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
Nepeta tenuifolia
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-
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?
geranyl diphosphate
(R)-limonene + diphosphate
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-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
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-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
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-
-
-
?
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Mg2+
may replace Mn2+ but with much lower efficiency (maximum activity at 20 mM)
Mg2+
-
Mn2+ or Mg2+ required
Mg2+
or Mn2+, reuired. Optimum concentraion 50 mM
Mn2+
required for activity, 0.4 mM used in assay conditions
Mn2+
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Mn2+ or Mg2+ required
Mn2+
the proportions of the products change significantly when Mn2+ is supplied instead of Mg2+
Mn2+
or Mg2+, required. Optimum concentration 0.2 mM, 68% of the efficieny with Mg2+. Product pattern changes markedly to 46% limonene, 9% terpinolene, 23% alpha-pinene, 5% beta-myrcene and 4% alpha-phellandrene, when Mn2+ is supplied instead of Mg2+
additional information
DDxxD motif, binding site for substrate-divalent metal cation complex
additional information
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DDxxD motif, binding site for substrate-divalent metal cation complex
additional information
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divalent metal ion required, probably Mn2+
additional information
divalent metal ion required, probably Mn2+
additional information
divalent metal ion required, probably Mn2+
additional information
not affected by K+ and Na+
additional information
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not affected by K+ and Na+
additional information
Nepeta tenuifolia
DDxxD motif, binding site for substrate-divalent metal cation complex
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2-Fluorogeranyl diphosphate
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competitive inhibitor
2-fluoroneryl diphosphate
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competitive inhibitor
geranyl diphosphate
substrate inhibition above 0.01 mM; substrate inhibition above 0.01 mM
K+
maximum inhibition above 100 mM; maximum inhibition above 100 mM
Mn2+
above 0.6 mM, activation below; above 0.6 mM, activation below
Mn2+
the enzyme is strongly inhibited at concentrations of more than 1 mM
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Mn2+
inhibition above 0.6 mM, activation below
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Infections
Terpene down-regulation triggers defense responses in transgenic orange leading to resistance against fungal pathogens.
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0.0007 - 0.0474
geranyl diphosphate
0.0007
geranyl diphosphate
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0.0131
geranyl diphosphate
at pH 8.0, temperature not specified in the publication
0.0474
geranyl diphosphate
pH 7.0, 30°C
0.0474
geranyl diphosphate
LaLIMS_RR, truncated protein
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0.00054
2-Fluorogeranyl diphosphate
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pH and temperature not specified in the publication
0.00024
2-fluoroneryl diphosphate
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pH and temperature not specified in the publication
0.012 - 0.186
geranyl diphosphate
0.012
geranyl diphosphate
LaLIMS_RR, truncated protein
0.186
geranyl diphosphate
at pH 8.0, temperature not specified in the publication
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0.255
geranyl diphosphate
pH 7.0, 30°C
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0.0024
2-Fluorogeranyl diphosphate
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pH and temperature not specified in the publication
0.0395
2-fluoroneryl diphosphate
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pH and temperature not specified in the publication
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7.6
Nepeta tenuifolia
assay at
7
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7
optimized assay, LaLIMS_RR, truncated protein
7.5
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7.5
standard activity assay
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23
standard activity assay
31
Nepeta tenuifolia
assay at
30
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30
optimized assay, LaLIMS_RR, truncated protein
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SwissProt
brenda
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brenda
Marc.
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brenda
cultivar Duncan
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brenda
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UniProt
brenda
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-
-
brenda
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SwissProt
brenda
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-
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brenda
-
SwissProt
brenda
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-
-
brenda
cultivar Navelina
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brenda
cultivars AS3, AS5 and EV Navelina and AS11, S13 and EV Pineapple
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brenda
cultivars Navelina and Pineapple
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brenda
navel orange
UniProt
brenda
-
UniProt
brenda
Marc.
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-
brenda
Nepeta tenuifolia
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SwissProt
brenda
Nepeta tenuifolia
production of the monoterpene limonene and modulation of apoptosis-related proteins in embryonic-mouse NIH 3T3 fibroblast cells by introduction of the limonene synthase gene isolated from japanese catnip
SwissProt
brenda
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Nepeta tenuifolia
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brenda
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brenda
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powerfully expressed at anthesis
brenda
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powerfully expressed at anthesis
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brenda
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brenda
peel of young developing fruit
brenda
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brenda
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brenda
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brenda
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brenda
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-
brenda
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brenda
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brenda
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brenda
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-
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brenda
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malfunction
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Drastic down-regulation of D-limonene synthase gene expression in the peel of transgenic oranges leads to fruit resistance against Penicillium digitatum, Xanthomonas citri subsp. citri and other specialized pathogens
malfunction
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enzyme down-regulation in orange fruit induces resistance against the fungus Phyllosticta citricarpa through enhanced accumulation of monoterpene alcohols and activation of defence
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RLC1_CITLI
606
0
70348
Swiss-Prot
Chloroplast (Reliability: 5 )
RLC1_CITSI
607
0
70354
Swiss-Prot
Chloroplast (Reliability: 2 )
BCGS_ORIVU
555
0
64443
Swiss-Prot
other Location (Reliability: 2 )
LALIM_LAVAN
602
0
70345
Swiss-Prot
Chloroplast (Reliability: 3 )
TPS1_TOOSI
595
0
68911
Swiss-Prot
Chloroplast (Reliability: 4 )
A0A2G9GEG6_9LAMI
606
0
70951
TrEMBL
other Location (Reliability: 4 )
B9S893_RICCO
250
0
28930
TrEMBL
other Location (Reliability: 4 )
B9RXW6_RICCO
180
0
20877
TrEMBL
Mitochondrion (Reliability: 4 )
A0A2G9GQ38_9LAMI
606
0
70759
TrEMBL
Mitochondrion (Reliability: 4 )
A0A2G9HPL8_9LAMI
607
0
70197
TrEMBL
Chloroplast (Reliability: 2 )
B9TL72_RICCO
143
0
17319
TrEMBL
other Location (Reliability: 2 )
B9S899_RICCO
226
0
26444
TrEMBL
other Location (Reliability: 3 )
B9S898_RICCO
192
0
22128
TrEMBL
other Location (Reliability: 4 )
A0A7C8YC60_OPUST
Opuntia cardona
289
0
33062
TrEMBL
other Location (Reliability: 3 )
A0A7C8YC60_OPUST
289
0
33062
TrEMBL
other Location (Reliability: 3 )
B9S897_RICCO
123
0
14157
TrEMBL
other Location (Reliability: 3 )
B9S8A3_RICCO
222
0
26283
TrEMBL
other Location (Reliability: 4 )
A0A7C9E4H7_OPUST
248
0
28453
TrEMBL
other Location (Reliability: 2 )
B9RH09_RICCO
599
0
69129
TrEMBL
Chloroplast (Reliability: 4 )
B9T537_RICCO
257
0
29569
TrEMBL
other Location (Reliability: 1 )
A0A6M9BIX0_9ROSI
399
0
46453
TrEMBL
Chloroplast (Reliability: 2 )
B9SXQ2_RICCO
351
0
40294
TrEMBL
other Location (Reliability: 3 )
B9RPM0_RICCO
596
0
68363
TrEMBL
Chloroplast (Reliability: 2 )
B9RPN5_RICCO
288
0
32558
TrEMBL
Secretory Pathway (Reliability: 5 )
Q6F5H2_CITUN
608
0
70511
TrEMBL
-
Q8L5K1_CITLI
606
0
70290
TrEMBL
-
Q940E7_AGARU
613
0
71423
TrEMBL
-
Q9FUW5_9LAMI
Nepeta tenuifolia
620
0
71810
TrEMBL
-
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60000
x * 60000, SDS-PAGE
62000
Nepeta tenuifolia
x * 62000, SDS-PAGE, x * 64000, deduced from gene sequence
64000
Nepeta tenuifolia
x * 62000, SDS-PAGE, x * 64000, deduced from gene sequence
70300
x * 70300, SDS-PAGE
70000
gel filtration
70000
-
1 * 70000, recombinant GST fusion protein, SDS-PAGE
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?
x * 60000, SDS-PAGE
?
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1 * 70000, recombinant GST fusion protein, SDS-PAGE
?
-
1 * 70000, recombinant GST fusion protein, SDS-PAGE
-
?
Nepeta tenuifolia
x * 62000, SDS-PAGE, x * 64000, deduced from gene sequence
monomer
1 * 70000, SDS-PAGE
monomer
1 * 65700, calculated from amino acid sequence
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apoenzyme, sitting drop vapor diffusion method, using 12-16% (w/v) PEG 8000 as precipitant
in complex with 2-fluorogeranyl diphosphate or 2-fluoroneryl diphosphate, vapor diffusion method
-
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Ni-Sepharose column chromatography
Ni2+-affinity column chromatography
-