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EC Tree
IUBMB Comments A cytochrome P-450 heme-thiolate protein. Involved in the insect aggregation pheromone production. Isolated from the pine engraver beetle, Ips pini. A small amount of (S)-ipsdienol is also formed. In vitro it also hydroxylated (+)- and (-)-alpha-pinene, 3-carene, and (+)-limonene, but not alpha-phellandrene, (-)-beta-pinene, gamma-terpinene, or terpinolene.
Word Map
1.14.14.31
carotid
intima-media
ultrasound
intima
cimts
b-mode
tracings
lumen-intima
media-adventitia
ospedale
sanatorium
The expected taxonomic range for this enzyme is: Ips
Synonyms
cyp9t2, cyp9t1, myrcene hydroxylase,
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CYP9T2
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CYP9T3
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-
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myrcene hydroxylase
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-
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myrcene + [reduced NADPH-hemoprotein reductase] + O2 = (R)-ipsdienol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
-
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myrcene,NADPH-hemoprotein reductase:O2 oxidoreductase (hydroxylating)
A cytochrome P-450 heme-thiolate protein. Involved in the insect aggregation pheromone production. Isolated from the pine engraver beetle, Ips pini. A small amount of (S)-ipsdienol is also formed. In vitro it also hydroxylated (+)- and (-)-alpha-pinene, 3-carene, and (+)-limonene, but not alpha-phellandrene, (-)-beta-pinene, gamma-terpinene, or terpinolene.
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(+)-alpha-pinene + NADPH + H+ + O2
verbenol + NADP+ + H2O
-
-
?
(-)-alpha-pinene + NADPH + H+ + O2
cis-verbenol + NADP+ + H2O
-
-
?
(-)-alpha-pinene + NADPH + H+ + O2
myrtenol + NADP+ + H2O
-
-
?
3-carene + NADPH + H+ + O2
?
-
-
?
myrcene + NADPH + H+ + O2
(4R)-(-)-ipsdienol + NADP+ + H2O
myrcene is 7-methyl-3-methylene-1,6-octadiene
81% yield, ipsidenol is 2-methyl-6-methylene-2,7-octadien-4-ol
?
myrcene + NADPH + H+ + O2
(R)-ipsdienol + NADP+ + H2O
-
85% yield
?
myrcene + NADPH + H+ + O2
ipsdienol + NADP+ + H2O
R-(+)-limonene + NADPH + H+ + O2
?
-
-
?
additional information
?
-
myrcene + NADPH + H+ + O2
ipsdienol + NADP+ + H2O
87% yield of (-)-ipsdienol, 13% yield of (+)-ipsdienol
-
?
myrcene + NADPH + H+ + O2
ipsdienol + NADP+ + H2O
the enzyme strongly prefers myrcene over other substrates
80% yield of (-)-ipsdienol, 20% yield of (+)-ipsdienol
?
additional information
?
-
no activity with alpha-phellandrene, (-)-beta-pinene, gamma-terpinene, or terpinolene
-
?
additional information
?
-
no activity with alpha-phellandrene, (-)-beta-pinene, gamma-terpinene, or terpinolene
-
?
additional information
?
-
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no activity with alpha-phellandrene, (-)-beta-pinene, gamma-terpinene, or terpinolene
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?
additional information
?
-
no activity with amitinol, E-myrcenol, linalool or geraniol
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?
additional information
?
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no activity with amitinol, E-myrcenol, linalool or geraniol
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?
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myrcene + NADPH + H+ + O2
(4R)-(-)-ipsdienol + NADP+ + H2O
myrcene is 7-methyl-3-methylene-1,6-octadiene
81% yield, ipsidenol is 2-methyl-6-methylene-2,7-octadien-4-ol
-
?
myrcene + NADPH + H+ + O2
(R)-ipsdienol + NADP+ + H2O
-
85% yield
-
?
myrcene + NADPH + H+ + O2
ipsdienol + NADP+ + H2O
myrcene + NADPH + H+ + O2
ipsdienol + NADP+ + H2O
87% yield of (-)-ipsdienol, 13% yield of (+)-ipsdienol
-
-
?
myrcene + NADPH + H+ + O2
ipsdienol + NADP+ + H2O
the enzyme strongly prefers myrcene over other substrates
80% yield of (-)-ipsdienol, 20% yield of (+)-ipsdienol
-
?
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NADPH
-
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8.9
calculated from amino acid sequence
9
calculated from amino acid sequence
9.5
calculated from amino acid sequence
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pinyon ips
UniProt
brenda
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UniProt
brenda
pine engraver beetle
UniProt
brenda
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-
brenda
-
brenda
-
brenda
-
brenda
-
brenda
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B8RBV1_9CUCU
532
0
60852
TrEMBL
-
M1JEK6_IPSPI
532
0
61065
TrEMBL
-
Q00G65_IPSPI
532
0
61059
TrEMBL
-
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65000
x * 65000, SDS-PAGE
61000
x * 61000, SDS-PAGE
61000
x * 61000, calculated from amino acid sequence
61000
x * 61000, calculated from amino acid sequence
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?
x * 65000, SDS-PAGE
?
x * 61000, calculated from amino acid sequence
?
x * 61000, calculated from amino acid sequence
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expressed in Sf9 cells
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CYP9T2 mRNA levels are not induced in adults exposed to myrcene-saturated atmosphere
expression levels are higher in males than females, and expression is significantly induced in male, but not in female, anterior midguts by feeding on host phloem
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Sandstrom, P.; Welch, W.H.; Blomquist, G.J.; Tittiger, C.
Functional expression of a bark beetle cytochrome P450 that hydroxylates myrcene to ipsdienol
Insect Biochem. Mol. Biol.
36
835-845
2006
Ips pini (Q00G65), Ips pini
brenda
Song, M.; Kim, A.C.; Gorzalski, A.J.; MacLean, M.; Young, S.; Ginzel, M.D.; Blomquist, G.J.; Tittiger, C.
Functional characterization of myrcene hydroxylases from two geographically distinct Ips pini populations
Insect Biochem. Mol. Biol.
43
336-343
2013
Ips pini (M1JEK6), Ips pini (Q00G65), Ips pini
brenda
Sandstrom, P.; Ginzel, M.D.; Bearfield, J.C.; Welch, W.H.; Blomquist, G.J.; Tittiger, C.
Myrcene hydroxylases do not determine enantiomeric composition of pheromonal ipsdienol in Ips spp.
J. Chem. Ecol.
34
1584-1592
2008
Ips confusus (B8RBV1), Ips confusus
brenda
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1.14.14.31 ipsdienol synthase
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