Information on EC 4.2.3.87 - alpha-guaiene synthase

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The expected taxonomic range for this enzyme is: Gunneridae

EC NUMBER
COMMENTARY
4.2.3.87
-
RECOMMENDED NAME
GeneOntology No.
alpha-guaiene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(2E,6E)-farnesyl diphosphate = alpha-guaiene + diphosphate
show the reaction diagram
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
(2Z,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, alpha-guaiene-forming)
Requires Mg2+. The enzyme from Pogostemon cablin gives 13% alpha-guaiene as well as 37% (-)-patchoulol (see EC 4.2.3.70), 13% delta-guaiene (see EC 4.2.3.93), and traces of at least ten other sesquiterpenoids [1]. In Aquilaria crassna three clones of the enzyme gave about 80% delta-guaiene and 20% alpha-guaiene, with traces of alpha-humulene. A fourth clone gave 54% delta-guaiene and 45% alpha-guaiene [2].
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Pat177
-
recombinant enzyme
patchoulol synthase
-
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
patchouli
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
alpha-guaiene + diphosphate
show the reaction diagram
-
-
13% yield
-
?
(2E,6E)-farnesyl diphosphate
alpha-guaiene + diphosphate
show the reaction diagram
Q49SP3
-
13% yield with recombinant enzyme
-
?
(2E,6E)-farnesyl diphosphate
alpha-guaiene + diphosphate
show the reaction diagram
-
-
main product with 29.4% yield
-
?
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
Q49SP3
Mg2+ is slightly preferred to Mn2+ with maximum activity observed at 1 mM Mg2+ and dropping to less than 10% at 0.1 mM Mg2+
Mn2+
Q49SP3
Mn2+ can substitute for Mg2+ at a concentration of 0.1 mM
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Mn2+
Q49SP3
concentrations higher than 0.1 mM are inhibitiory
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.00445
-
(2E,6E)-farnesyl diphosphate
Q49SP3
pH 7.0, 30C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.00043
-
(2E,6E)-farnesyl diphosphate
Q49SP3
pH 7.0, 30C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7
7.5
Q49SP3
-
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7
9
Q49SP3
75% of the maximum activity is recorded at pH 8.0-9.0. Enzyme activity is dramatically reduced below pH 7.0, but is rather stable above this pH value
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
40
-
Q49SP3
-
TEMPERATURE RANGE
TEMPERATURE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
20
40
Q49SP3
at 30C, the enzymatic activity is less than 60% of the activity measured at 40C and at 20C this value is 30%
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
Q49SP3
x * 55000, SDS-PAGE; x * 64000, calculated from amino acid sequence
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Ni-NTA column chromatography, gel filtration
-
Ni2+ affinity column chromatography
Q49SP3
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in Escherichia coli BL21 (DE3) Codon Plus-RIL cells
-
expressed in Escherichia coli
Q49SP3
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
the production of alpha-guaiene is induced by treatment with methyl jasmonate
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
W144R/V241E/P296S/H337Y
-
inactive
Y110S/V241E/P296S/H337Y
-
the mutant produces 34.1% alpha-guaiene, 1.3% alpha-humulene and 64.6% delta-guaiene
Y110S/W144R/P296S/H337Y
-
inactive
Y110S/W144R/V241E/H337Y
-
inactive
Y110S/W144R/V241E/P296S
-
inactive
Y110S/W144R/V241E/P296S/H337Y
-
the mutant produces 31.1% alpha-guaiene, 1.5% alpha-humulene and 67.4% delta-guaiene