2.5.1.21: squalene synthase
This is an abbreviated version!
For detailed information about squalene synthase, go to the full flat file.
Word Map on EC 2.5.1.21
-
2.5.1.21
-
farnesylation
-
cholesterol
-
prenylation
-
sterol
-
ftase
-
mevalonate
-
geranylgeranylation
-
isoprenoids
-
leukemia
-
geranylgeranyltransferase
-
pyrophosphate
-
tipifarnib
-
hmg-coa
-
statin
-
h-ras
-
peptidomimetic
-
epoxidase
-
prenyltransferase
-
dolichols
-
rhob
-
isoprenylation
-
triterpene
-
farnesol
-
3-hydroxy-3-methylglutaryl
-
lamins
-
ergosterol
-
cholesterol-lowering
-
hmgcr
-
prelamin
-
p21ras
-
lovastatin
-
hutchinson-gilford
-
lanosterol
-
manumycin
-
triterpenoids
-
synthesis
-
progerin
-
farnesylpyrophosphate
-
cis-prenyltransferase
-
drug development
-
oxidosqualene
-
ras-transformed
-
medicine
-
ras-dependent
-
nonsterols
-
ras-mediated
-
withanolides
-
srebp-2
-
ganoderic
-
agriculture
-
geranylgeraniol
-
industry
-
cycloartenol
-
non-thiol
-
2,3-oxidosqualene
- 2.5.1.21
-
farnesylation
- cholesterol
-
prenylation
- sterol
- ftase
- mevalonate
-
geranylgeranylation
-
isoprenoids
- leukemia
-
geranylgeranyltransferase
- pyrophosphate
- tipifarnib
- hmg-coa
- statin
- h-ras
-
peptidomimetic
-
epoxidase
- prenyltransferase
- dolichols
- rhob
-
isoprenylation
-
triterpene
- farnesol
-
3-hydroxy-3-methylglutaryl
- lamins
- ergosterol
-
cholesterol-lowering
- hmgcr
-
prelamin
-
p21ras
- lovastatin
-
hutchinson-gilford
- lanosterol
- manumycin
-
triterpenoids
- synthesis
-
progerin
-
farnesylpyrophosphate
- cis-prenyltransferase
- drug development
- oxidosqualene
-
ras-transformed
- medicine
-
ras-dependent
-
nonsterols
-
ras-mediated
-
withanolides
- srebp-2
-
ganoderic
- agriculture
- geranylgeraniol
- industry
- cycloartenol
-
non-thiol
- 2,3-oxidosqualene
Reaction
2 (2E,6E)-farnesyl diphosphate + + = + 2 diphosphate +
Synonyms
BbSS, BSS, CrSQS, dt-ySQase, Erg9, EtSS, farnesyl-diphosphate farnesyltransferase, farnesyl-diphosphate:farnesyldiphosphate farnesyltransferase, farnesyldiphosphate farnesyltransferase 1, farnesyldiphosphate:farnesyldiphosphate farnesyltransferase, farnesyltransferase, FDFT1, hSQS, presqualene synthase, presqualene-diphosphate synthase, SgSQS, SQase, SQS, SQS1, SQS2, squalene synthase, squalene synthase 1, squalene synthase 2, squalene synthetase, SS1, SSase, SSN, synthase, squalene, TkSQS1, TkSQS2
ECTree
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Substrates Products
Substrates Products on EC 2.5.1.21 - squalene synthase
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REACTION DIAGRAM
(2E,6E)-3,7,10-trimethylundeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
-
weak
-
-
?
(2E,6E)-3,7,11-trimethyldodeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
-
-
-
-
?
(2E,6E)-3,7,12-trimethyltrideca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
-
weak
-
-
?
(2E,6E)-3,7-dimethyldodeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
-
-
-
-
?
(2E,6E)-3,7-dimethyltetradeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
-
weak
-
-
?
(2E,6E)-3,7-dimethyltrideca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
-
weak
-
-
?
(2E,6E)-3,7-dimethylundeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
-
weak
-
-
?
(2E,6E)-farnesyl diphosphate + NADH + H+
squalene + diphosphate + NAD+
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + diphosphate + NADP+
-
-
-
-
?
(E,E)-7-desmethylfarnesyl diphosphate + NADPH
6,19-didesmethylsqualene + NADP+ + diphosphate
-
at 60% of the efficiency that farnesyl diphosphate is converted to squalene
in absence of farnesyl diphosphate, 6-desmethylsqualene is produced in presence of farnesyl diphosphate
?
10,11-dihydrofarnesyl diphosphate + NADPH
2,3,22,23-tetrahydrosqualene + NADP+ + diphosphate
-
at 60% of the efficiency that farnesyl diphosphate is converted to squalene
-
?
2 farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
farnesyl diphosphate + NADPH + H+
squalene + diphosphate + NADP+
Thermosynechococcus vestitus
-
-
sole product
-
?
2 (2E,6E)-farnesyl diphosphate
diphosphate + presqualene diphosphate
first half-reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate
diphosphate + presqualene diphosphate
first reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate
diphosphate + presqualene diphosphate
first reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
squalene + 2 diphosphate + NAD(P)+
-
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NAD(P)H + H+
squalene + 2 diphosphate + NAD(P)+
-
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NAD(P)H + H+
squalene + 2 diphosphate + NAD(P)+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NAD(P)H + H+
squalene + 2 diphosphate + NAD(P)+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NAD(P)H + H+
squalene + 2 diphosphate + NAD(P)+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NAD(P)H + H+
squalene + 2 diphosphate + NAD(P)+
overall reaction
-
-
?
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
the enzyme initially catalyzes the condensation of two molecules of farnesyl diphosphate (FPP) to form presqualene diphosphate (PSPP), and next converting PSPP to squalene in a reaction requiring NADPH and Mg2+
product analysis by GC-MS analysis
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction, the enzyme catalyzes the two-step reductive head-to-head condensation of two molecules of farnesyl pyrophosphate to form squalene using presqualene diphosphate (PSPP) as an intermediate
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
specific for, the enzyme catalyzes a head-to-head condensation reaction (1'-2,3-linked) between two molecules of farnesyl diphosphate (C15) forms a cyclopropylcarbinyl intermediate, presqualene diphosphate. The subsequent conversion of presqualene diphosphate to squalene involves an extensive rearrangement of the carbon skeleton and an NADPH-dependent reduction reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
squalene synthase catalyzes the first enzymatic step from the central isoprenoid pathway toward sterol and triterpenoid biosynthesis
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
farnesyl diphosphate forms hydrogen bonds with enzyme residues Arg49, Arg74, Ser48, and Val47 of conserved 77DTVED81 motif
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
farnesyl diphosphate forms hydrogen bonds with enzyme residues Asp81, Asp217, Glu80, and Gln206 of conserved 77DTVED81 and 213DYLED217 motifs
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
the enzyme catalyzes the first dedicated step in the biosynthesis of sterols and other triterpenoids
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
Thermosynechococcus vestitus
-
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
the enzyme is involved in celastrol biosynthesis
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
overall reaction
-
-
?
2 farnesyl diphosphate
presqualene diphosphate + diphosphate
-
-
-
?
2 farnesyl diphosphate
presqualene diphosphate + diphosphate
-
assay at pH 7.2, 30°C, 3 h
-
-
?
2 farnesyl diphosphate
presqualene diphosphate + diphosphate
Thermosynechococcus vestitus
-
-
in absence of NADPH, formation of presqualene diphosphate
-
?
11-methylsqualene + NADP+ + diphosphate
-
-
-
?
2-methylfarnesyl diphosphate + NADPH
11-methylsqualene + NADP+ + diphosphate
-
-
-
?
10-demethylsqualene + NADP+ + diphosphate
-
-
-
?
3-demethylfarnesyl diphosphate + NADPH
10-demethylsqualene + NADP+ + diphosphate
-
-
-
?
12,13-cis-dehydrosqualene + diphosphate
-
-
-
?
farnesyl diphosphate
12,13-cis-dehydrosqualene + diphosphate
-
in presence of Mn2+
12-cis-dehydrosqualene + diphosphate
?
diphosphate + presqualene diphosphate
-
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
enzyme may be important during response to infection and inflammation
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
first pathway-specific enzyme in cholesterol biosynthesis
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
squalene is the first sterol intermediate in cholesterol biosynthesis
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
enzyme may be important during response to infection and inflammation
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
-
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
first pathway-specific enzyme in cholesterol biosynthesis
-
-
?
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
-
essential enzyme in cholesterol biosynthetic pathway
-
-
?
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
-
?
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
-
-
presqualene diphosphate and squalene are produced in a ratio of 6:1
?
farnesyl diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
-
-
-
-
?
squalene + NAD(P)+ + diphosphate
-
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
in presence of reducing pyridine nucleotide, preferably NADPH, squalene is formed, in absence of reducing cofactor the rate of the condensation reaction is lower and all of the product accumulates as presqualene diphosphate
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
in presence of reducing pyridine nucleotide, preferably NADPH, squalene is formed, in absence of reducing cofactor the rate of the condensation reaction is lower and all of the product accumulates as presqualene diphosphate
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
in presence of reducing pyridine nucleotide, preferably NADPH, squalene is formed, in absence of reducing cofactor the rate of the condensation reaction is lower and all of the product accumulates as presqualene diphosphate
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
presqualene diphosphate synthetase and squalene synthetase are copurified during isolation
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
a single active site catalyzes both reactions
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
one protein with 2 catalytic sites may be involved in synthesis of presqualene diphosphate and for its reduction to squalene
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
the polymeric form of the enzyme also catalyzes the reduction of presqualene diphosphate by NADPH to squalene
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
-
in presence of reducing pyridine nucleotide, preferably NADPH, squalene is formed, in absence of reducing cofactor the rate of the condensation reaction is lower and all of the product accumulates as presqualene diphosphate
-
?
squalene + diphosphate + NAD(P)+
-
-
-
-
?
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
-
-
-
?
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
-
-
-
-
?
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
-
-
-
-
?
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
-
-
-
-
?
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
second reaction
-
-
?
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
second reaction
-
-
?
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
-
-
-
-
?
squalene + diphosphate + NADP+
-
-
-
?
presqualene diphosphate + NADPH + H+
squalene + diphosphate + NADP+
second half reaction
-
-
?
presqualene diphosphate + NADPH + H+
squalene + diphosphate + NADP+
-
-
-
-
?
presqualene diphosphate + NADPH + H+
squalene + diphosphate + NADP+
-
-
-
?
?
-
squalene and botryococcene are branched-chain, triterpene compounds that arise from the head-to-head condensation of two molecules of farnesyl diphosphate to yield 1'-1 and 1'-3 linkages, respectively. Different enzymes are responsible for botryococcene and squalene biosynthesis in the green alga Botryococcus braunii race B. The specificity for the 1'-1 and 1'-3 linkages is controlled by residues in the active sites that can mediate catalytic specificity. Identification of several amino acid positions contributing to the rearrangement of the cyclopropyl intermediate to squalene, The same positions do not appear to be sufficient to account for the cyclopropyl rearrangement to give botryococcene, oerview
-
-
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additional information
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squalene and botryococcene are branched-chain, triterpene compounds that arise from the head-to-head condensation of two molecules of farnesyl diphosphate to yield 1'-1 and 1'-3 linkages, respectively. Different enzymes are responsible for botryococcene and squalene biosynthesis in the green alga Botryococcus braunii race B. The specificity for the 1'-1 and 1'-3 linkages is controlled by residues in the active sites that can mediate catalytic specificity. Identification of several amino acid positions contributing to the rearrangement of the cyclopropyl intermediate to squalene, The same positions do not appear to be sufficient to account for the cyclopropyl rearrangement to give botryococcene, oerview
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analysis of substrate specificity, overview
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analysis of substrate specificity, overview
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the catalytic process involves two reactions: firstly, two FPP molecules are condensed to form presqualene diphosphate (PSPP), an intermediate with a cyclopropane C1'-C2-C3 ring structure, and secondly, PSPP undergoes a NADPH-dependent rearrangement and reduction to generate the end product squalene
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the catalytic process involves two reactions: firstly, two FPP molecules are condensed to form presqualene diphosphate (PSPP), an intermediate with a cyclopropane C1'-C2-C3 ring structure, and secondly, PSPP undergoes a NADPH-dependent rearrangement and reduction to generate the end product squalene
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enzyme is key regulator not only for phytosterol but also for triterpene biosynthesis
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enzyme is key regulator not only for phytosterol but also for triterpene biosynthesis
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none of the following analogues gives nonpolar products: 7,11-dimethyl-3-ethyl-2,6,10-dodecatrienyl diphosphate, 6,7,10,11-tetrahydrofarnesyl diphosphate, 4-methylthiofarnesyl diphosphate, 4-fluorofarnesyl diphosphate
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none of the following analogues gives nonpolar products: 7,11-dimethyl-3-ethyl-2,6,10-dodecatrienyl diphosphate, 6,7,10,11-tetrahydrofarnesyl diphosphate, 4-methylthiofarnesyl diphosphate, 4-fluorofarnesyl diphosphate
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reaction is completely regioselective
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no substrate: 6,7-dihydrofarnesyl diphosphate, 3-desmethylfarnesyl diphosphate
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not metabolized: (E)-6,7,10,11-tetrahydrofarnesyl diphosphate
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replacement of 3-methyl of farnesyl diphosphate by an ethyl group or introduction of a methyl group at C-4 results in a complete loss of activity
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