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IUBMB Comments Requires Mn2+. Mg2+ is not effective . Some (-)-alpha-phellandrene is also formed . The reaction involves a 1,3-hydride shift .
Word Map
4.2.3.52
laryngectomy
laryngeal
oncological
endoscopic
arytenoid
five-year
surgeon
laryngological
epiglottis
non-surgical
grandis
oleoresin
intraoperatively
supraglottic
larynx
piriform
dysfunction-free
conifers
abies
limonene
cr
supracricoid
gastrostomy
The enzyme appears in viruses and cellular organisms
Synonyms
ophls, phellandrene synthase, (-)-beta-phellandrene synthase,
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(-)-(4S)-beta-phellandrene synthase
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(-)-beta-phellandrene synthase
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beta-phellandrene synthase
phellandrene synthase
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-
beta-phellandrene synthase
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beta-phellandrene synthase
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-
beta-phellandrene synthase
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beta-phellandrene synthase
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beta-phellandrene synthase
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PHLS
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geranyl diphosphate = (4S)-beta-phellandrene + diphosphate
geranyl diphosphate = (4S)-beta-phellandrene + diphosphate
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-
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geranyl diphosphate = (4S)-beta-phellandrene + diphosphate
a 1,3-hydride shift from C3 to C8 of the cyclohexene nucleus is involved in the formation of phellandrene
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geranyl-diphosphate diphosphate-lyase [cyclizing; (4S)-beta-phellandrene-forming]
Requires Mn2+. Mg2+ is not effective [1]. Some (-)-alpha-phellandrene is also formed [3]. The reaction involves a 1,3-hydride shift [4].
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geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
geranyl diphosphate
beta-myrcene + beta-phellandrene + beta-pinene + alpha-phellandrene + diphosphate
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-
-
?
geranyl diphosphate
beta-phellandrene + beta-myrcene + beta-pinene + diphosphate
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-
-
?
geranyl diphosphate
beta-phellandrene + beta-pinene + beta-myrcene + diphosphate
neryl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
?
neryl diphosphate
beta-phellandrene + diphosphate
enzyme displays a clear preference for geranyl diphosphate over neryl diphosphate
in addition, enzyme produces small quantities of limonene
-
?
additional information
?
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no substrate: farnesyl diphosphate
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-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
soluble enzyme preparations from Escherichia coli BL21(DE3)/pSAG8(M), expressing (-)-beta-phellandrene synthase convert geranyl diphosphate to four products. beta-phellandrene (52%) as the major olefin, and lesser amounts of (1S,5S)-beta-pinene (34%), (1S,5S)-apinene (8.5%), and (4S)-limonene (6%) are identified. The stereochemistry of beta-phellandrene is not confirmed directly. Nevertheless, stereochemical considerations based on the established absolute configuration of the coproducts, and the natural occurrence of (4S)-beta-phellandrene in the turpentine, suggests that the biosynthetic product is the mechanistically related (4S)-antipode derived via the (3S)-linalyl diphosphate intermediate. The product of the ag8 gene is therefore designated (4S)-beta-phellandrene synthase
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-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
enzyme displays a clear preference for geranyl diphosphate over neryl diphosphate
in addition, enzyme produces small quantities of limonene
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
a 1,3-hydride shift from C3 to C8 of the cyclohexene nucleus is involved in the formation of phellandrene
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
some (-)-alpha-phellandrene is also formed. Both phellandrene isomers are generated from a common phellandryl cation by the cyclase
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-
?
geranyl diphosphate
beta-phellandrene + beta-pinene + beta-myrcene + diphosphate
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-
-
-
?
geranyl diphosphate
beta-phellandrene + beta-pinene + beta-myrcene + diphosphate
-
-
-
?
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geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
neryl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
-
-
?
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Fe2+
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the enzyme requires either Mn2+ or Fe2+ as divalent metal ion cofactor
Mn2+
-
the enzyme requires either Mn2+ or Fe2+ as divalent metal ion cofactor, maximal activity at 1 mM MnCl2
additional information
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no activation by Mg2+, Li+ or Na+
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diethyl dicarbonate
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lack of substrate protection against inactivation
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Carcinoma
Re-Evaluation of Open Partial Horizontal Laryngectomies at Our Institution According to the New Classification Recommended by the European Laryngological Society.
Laryngeal Neoplasms
Open partial horizontal laryngectomy and adjuvant (chemo)radiotherapy for laryngeal squamous cell carcinoma: results from a multicenter Italian experience.
Neoplasms
Treatment for T3 to T4a laryngeal cancer by open partial horizontal laryngectomies: Prognostic impact of different pathologic tumor subcategories.
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0.00655 - 0.0078
geranyl diphosphate
0.00655
geranyl diphosphate
pH 6.5, 30°C
0.0078
geranyl diphosphate
-
32°C
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0.017
geranyl diphosphate
pH 6.5, 30°C
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2.83
geranyl diphosphate
pH 6.5, 30°C
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6.6 - 8.5
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50% of maximal activity at pH 6.6 and at pH 8.5
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4.75
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isoelectric focusing
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SwissProt
brenda
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UniProt
brenda
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UniProt
brenda
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UniProt
brenda
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-
-
brenda
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-
-
brenda
Douglas var. latifolia Engelman
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-
brenda
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very poor expression
brenda
strong expression in young leaf
brenda
-
-
brenda
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of 2-year-old Pinus contorta
brenda
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-
brenda
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SPIN1_PINBN
623
0
71422
Swiss-Prot
Chloroplast (Reliability: 3 )
TPSD8_ABIGR
630
0
72784
Swiss-Prot
Chloroplast (Reliability: 3 )
BPHL1_PINBN
621
0
71559
Swiss-Prot
Chloroplast (Reliability: 4 )
BPHL1_PINCO
621
0
71452
Swiss-Prot
Chloroplast (Reliability: 4 )
BPHL2_PINCO
624
0
72021
Swiss-Prot
Chloroplast (Reliability: 5 )
BPHS1_PICSI
624
0
71417
Swiss-Prot
Chloroplast (Reliability: 2 )
BPHS2_PICSI
624
0
71427
Swiss-Prot
Chloroplast (Reliability: 2 )
BPHS3_PICSI
624
0
71439
Swiss-Prot
Chloroplast (Reliability: 2 )
BPHS4_PICSI
624
0
71408
Swiss-Prot
Chloroplast (Reliability: 1 )
E9N3U9_LAVAN
581
0
68260
TrEMBL
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62300
x * 62300, calculated, including transit peptide, x * 62300, recombinant protein including His-Tag, SDS-PAGE
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?
x * 62300, calculated, including transit peptide, x * 62300, recombinant protein including His-Tag, SDS-PAGE
monomer
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1 * 67000, SDS-PAGE
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the enzyme is extremely sensitive to thiol oxidation. Cyclase activity is completely lost when the partially purified xylem preparation is dialyzed against buffer (pH 7.8) devoid of thiol-protecting reagents (dithiothreitol or 2-mercaptoethanol). Other reducing agents, such as sodium ascorbate (5 mM) or sodium metabisulfite (5 mM), fail to protect the cyclases from inactivation, whereas readdition of 5 mM dithiothreitol to the dialyzed preparations restores 54% of the original activity
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704380
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0-4°C, partially purified preparation is very stable
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expressed in Synechocystis sp. PCC 6803
expression in Escherichia coli
expressed in Synechocystis sp. PCC 6803
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expressed in Synechocystis sp. PCC 6803
expressed in Synechocystis sp. PCC 6803
expressed in Synechocystis sp. PCC 6803
expression in Escherichia coli
expression in Escherichia coli
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LaFever, R.E.; Croteau, R.
Hydride shifts in the biosynthesis of the p-menthane monoterpenes alpha-terpinene, gamma-terpinene, and beta-phellandrene
Arch. Biochem. Biophys.
301
361-366
1993
Pinus contorta
brenda
Savage, T.J.; Ichii, H.; Hume, S.D.; Little, D.B.; Croteau, R.
Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents
Arch. Biochem. Biophys.
320
257-265
1995
Pinus contorta
brenda
Bohlmann, J.; Phillips, M.; Ramachandiran, V.; Katoh, S.; Croteau, R.
cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)
Arch. Biochem. Biophys.
368
232-243
1999
Abies grandis (Q9M7D1), Abies grandis
brenda
Savage, T.J.; Hatch, M.W.; Croteau, R.
Monoterpene synthases of Pinus contorta and related conifers. A new class of terpenoid cyclase
J. Biol. Chem.
269
4012-4020
1994
Pinus contorta
brenda
Wagschal, K.; Savage, T.J.; Croteau, R.
Isotopically sensitive branching as a tool for evaluating multiple product formation by monoterpene cyclases
Tetrahedron
31
5933-5944
1991
Pinus contorta
-
brenda
Demissie, Z.; Sarker, L.; Mahmoud, S.
Cloning and functional characterization of beta-phellandrene synthase from Lavandula angustifolia
Planta
233
685-696
2011
Lavandula angustifolia (E9N3U9)
brenda
Formighieri, C.; Melis, A.
Cyanobacterial production of plant essential oils
Planta
248
933-946
2018
Lavandula angustifolia, Picea sitchensis (C0PTH8), Abies grandis (Q9M7D1), Pinus banksiana (R9QMW7)
brenda
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4.2.3.52 (4S)-beta-phellandrene synthase (geranyl-diphosphate-cyclizing)
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