5.4.99.17: squalene-hopene cyclase
This is an abbreviated version!
For detailed information about squalene-hopene cyclase, go to the full flat file.
Word Map on EC 5.4.99.17
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5.4.99.17
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cyclization
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alicyclobacillus
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acidocaldarius
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hopanoids
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cyclases
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oxidosqualene
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pentacyclic
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triterpene
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2,3-oxidosqualene
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tetracyclic
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tetrahymanol
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carbocation
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polyolefinic
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5.4.99.7
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lanosterol
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aspartate-rich
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synthesis
- 5.4.99.17
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cyclization
- alicyclobacillus
- acidocaldarius
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hopanoids
- cyclases
- oxidosqualene
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pentacyclic
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triterpene
- 2,3-oxidosqualene
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tetracyclic
- tetrahymanol
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carbocation
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polyolefinic
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5.4.99.7
- lanosterol
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aspartate-rich
- synthesis
Reaction
Synonyms
AacSHC, cyclase, squalene-hopanoid, SHC, SHC1, SHC2, Spterp25, SQ-hopene cyclase, squalene hopene cyclase, squalene-hopene cyclase, ZmoSHC1, ZmSHC1
ECTree
Advanced search results
Engineering
Engineering on EC 5.4.99.17 - squalene-hopene cyclase
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F481C
YP3187836
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
C435S/D374I/D374V/H451F
D376C
D376E
D376G
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0.2% activity when enzyme concentration is increased to 100fold
D377C/D377N/Y612A
D377E
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0.2% activity when enzyme concentration is increased to 100fold
D377E/D376Q/D376R/D377R/E45K/W406V/W417A/D377C
D377G
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0.2% activity when enzyme concentration is increased to 100fold
D377Q
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0.2% activity when enzyme concentration is increased to 100fold
E45A
E93A
F365A
F365C
F365G
the mutant shows increased activity with (S)-6,7-epoxygeraniol and no activity with geraniol compared to the wild type enzyme
F365W
F365Y
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and mutant with F365 changed to unnatural amino acid O-methyltyrosine. Both show increased decreased activity at high temperature
F434A
F437A
F601A
F605A
F605W
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increased catalytic acitivy at low temperature, but decreased activity at high temperature due to higher cation-pi binding energies
F605Y
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and mutant with F605 changed to unnatural amino acid O-methyltyrosine. Both show increased catalytic acitivy at low temperature, but decreased activity at high temperature due to higher cation-pi binding energies
G262A
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the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
G600F
the mutant exhibits 68% conversion of geraniol to cyclogeraniol hydrate
I261A
I261W
the mutant shows increased activity with (S)-6,7-epoxygeraniol and no activity with geraniol compared to the wild type enzyme
L36A
the mutant shows increased activity with (S)-6,7-epoxygeraniol compared to the wild type enzyme
P263A
P263G
Q262A
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mutation located between C29 of the hopanyl cation and the "front water"
Q262G
Q262G/Q262A/P263G/P263A
R127Q
S307A
the mutant shows increased activity with (S)-6,7-epoxygeraniol and no activity with geraniol compared to the wild type enzyme
T41A
V380E
V381A/D376C
W133A
W169A
W169F/W169H/W489A/F605K
W23V
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same activity and optimal temperature as wild type enzyme
W312G
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the mutant produces (-)-neo-isopulegol from (S)-citronellal
W485V
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same activity and optimal temperature as wild type enzyme
W522V
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same activity and optimal temperature as wild type enzyme
W533A
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same activity and optimal temperature as wild type enzyme
W591L
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same activity and optimal temperature as wild type enzyme
W78S
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same activity and optimal temperature as wild type enzyme
Y267A
Y420A
Y420C
Y420W
the mutant exhibits 54% conversion of (S)-6,7-epoxygeraniol to (1S,3R)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol
Y420W/G600F
the mutant exhibits 78% conversion of (S)-6,7-epoxygeraniol to (1S,3R)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol
Y606A/W23V/W495V/W522V/W533A/W591L/W78S/E35Q/E197Q/D530N/T378A
Y609A
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the mutant produces (+)-isopulegol from (S)-citronellal
Y609A/Y612A/L607K
Y609F
Y612F/D376E/D376G/D377E/D377G/D377Q/E45A/E45D/F365W/T41A/E93A/R127Q/W133A/Y267A/F434A/F437A/W258L/D350N/D421N/D442N/H451R/D447N/D377N/D313N/E535Q/D374E
Y420C
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site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
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A306F
the mutant produces apolypodatetraene, gamma-polypodatetraene and neopolypoda-5(6),13,17,21-teraene from squalene and polypoda-8(9),13,17,21-tetraen-3a-ol, polypoda-7(8),13,17,21-tetraen-3alpha-ol and polypoda-7(8),13,17,21-tetraen-3beta-ol from a racemic mixture of (3S)-2,3-oxidosqualene and (3R)-2,3-oxidosqualene
A306T
the mutant produces (20R)-dammara-13(17),24-dien-3a-ol, (20R)-dammara-13(17),24-dien-3b-ol, (20R)-dammara-12(13),24-dien-3a-ol, (20R)-dammara-12(13),24-dien-3b-ol and (20R,24R)-17-epi-epoxydammarane from a racemic mixture of (3S)-2,3-oxidosqualene and (3R)-2,3-oxidosqualene
A306V
the mutant produces apolypodatetraene, dammara-13(17)-24-diene, gamma-polypodatetraene, (17E)(13aH)-malabarica-14(27),17,21-triene, (20R)-dammara-12(13),24-diene, (20R)-eupha-7(8),24-diene, (20S)-tirucalla-7(8),24-diene, and 17-epi-dammara-20(21),24-diene from squalene
F129L
the mutant shows a (E,E)-homofarnesol conversion at 24 h of reaction which is comparable to the wild type enzyme
F129L/F601Y
the mutant shows lower (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
F129L/M132R/I432T
the mutant shows much lower (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
F129L/M132R/I432T/F601Y
the mutant shows much lower (E,E)-homofarnesol conversion compared to the wild type enzyme
F365C
the mutant is able to convert geraniol into (S)-gamma-cyclogeraniol and cyclogeraniol hydrate
F601Y
the mutant shows a (E,E)-homofarnesol conversion at 24 h of reaction which is comparable to the wild type enzyme
G600F
the mutant is able to convert geraniol into (S)-gamma-cyclogeraniol and cyclogeraniol hydrate
I261A
the mutant exclusively converts (S)-citronellal to ( -)-iso-isopulegol isomer (1R,2S,5S)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol with an 11times improved activity as compared to the wild type enzyme
L607F
the mutant produces the farnesyl ether with 6times higher yield from farnesol than the wild type enzyme
M132R/A224V/I432T
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
M132R/I432T
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
M132R/I432T/F601Y
the mutant shows much lower (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
Q579H/F601Y
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
T77A/I92V/F129L
the mutant shows better (E,E)-homofarnesol conversion at 24 h of reaction compared to the wild type enzyme
Y420W/G600F
the mutant produces selectively (1S)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol from 6,7-epoxygeraniol with a conversion of up to 78%
F409C
Q81YD8
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F447C
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site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
F436C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F450C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F436C
Burkholderia ambifaria ATCC BAA-244 / AMMD
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site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
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F450C
Burkholderia ambifaria ATCC BAA-244 / AMMD
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site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
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F445C
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site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F438C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F457C
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F438C
F486C
site-directed mutagenesis, the mutant shows increased activity in interconversion of citronellal and isopulegol compared to the wild-type enzyme
W555A
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555C
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555D
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and moderate citronellal cyclase activity
W555E
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and low citronellal cyclase activity
W555F
W555G
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555H
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and moderate citronellal cyclase activity
W555I
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555K
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555L
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555M
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and low citronellal cyclase activity
W555N
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and moderate citronellal cyclase activity
W555P
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555Q
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity, and low citronellal cyclase activity
W555R
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555S
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555T
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and higher citronellal cyclase activity
W555V
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and low citronellal cyclase activity
W555Y
F438C
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site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
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F486C
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site-directed mutagenesis, the mutant shows increased activity in interconversion of citronellal and isopulegol compared to the wild-type enzyme
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W555F
W555Y
additional information
C435S/D374I/D374V/H451F
site-directed mutagenesis, inactive mutant
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
D377C/D377N/Y612A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
inactive mutant
D377E/D376Q/D376R/D377R/E45K/W406V/W417A/D377C
site-directed mutagenesis, inactive mutant
E45A
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production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
E93A
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production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F365A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F365A
the mutant shows increased activity with geraniol and (S)-6,7-epoxygeraniol compared to the wild type enzyme
the mutant exhibits 15% conversion of geraniol to gamma-cyclogeraniol
F365C
the mutant shows increased activity with geraniol compared to the wild type enzyme
F434A
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production of hop-22(29)-ene is decreased, production of hopanol is markedly increased at lower temperatures
F437A
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production of hop-22(29)-ene is decreased, production of hopanol is markedly increased at lower temperatures
F601A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F601A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F605A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
F605A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
I261A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
I261A
the mutant exhibits 11% conversion of citronellal to (-)-iso-isopulegol. The mutant shows increased activity with geraniol and (S)-6,7-epoxygeraniol compared to the wild type enzyme
I261A
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the mutant has higher activity with (S)-citronellal compared to the wild type enzyme
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mutation located between C29 of the hopanyl cation and the "front water"
P263A
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the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
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mutation located between C29 of the hopanyl cation and the "front water"
P263G
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the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
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mutation located between C29 of the hopanyl cation and the "front water"
Q262G
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the mutant produces hopanol as the main product instead of hop-22(29)-ene. The mutant also produces hop-21(22)ene
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Q262G/Q262A/P263G/P263A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
R127Q
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production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
T41A
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production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
V381A/D376C
site-directed mutagenesis, inactive mutant
W133A
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production of hop-22(29)-ene is less throughout the entire temperature range than that by the wild-type. Hop-21(22)ene is not produced
W169A
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the mutant has higher activity with (S)-citronellal compared to the wild type enzyme
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
W169F/W169H/W489A/F605K
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y267A
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production of hop-22(29)-ene is decreased, production of hopanol is markedly increased at lower temperatures
Y420A
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y420A
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y420C
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
the mutant shows the same product pattern and activity as the wild-type
Y606A/W23V/W495V/W522V/W533A/W591L/W78S/E35Q/E197Q/D530N/T378A
site-directed mutagenesis, the mutant shows the same product pattern and activity as the wild-type
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609A/Y612A/L607K
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609F
the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609F
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview
Y609F
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme, overview. The phenotype of Y609F mutein is contrarily described in two publications
Y612F/D376E/D376G/D377E/D377G/D377Q/E45A/E45D/F365W/T41A/E93A/R127Q/W133A/Y267A/F434A/F437A/W258L/D350N/D421N/D442N/H451R/D447N/D377N/D313N/E535Q/D374E
the mutant shows the same product pattern as the wild-type with less enzyme activity
Y612F/D376E/D376G/D377E/D377G/D377Q/E45A/E45D/F365W/T41A/E93A/R127Q/W133A/Y267A/F434A/F437A/W258L/D350N/D421N/D442N/H451R/D447N/D377N/D313N/E535Q/D374E
site-directed mutagenesis, the mutant shows the same product pattern as the wild-type with less enzyme activity
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site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
F438C
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and higher citronellal cyclase activity
W555F
W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity,and higher citronellal cyclase activity
W555Y
W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
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site-directed mutagenesis, the mutant shows no squalene hopene cyclase activity, and higher citronellal cyclase activity
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W555F
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W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
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site-directed mutagenesis, the mutant shows highly reduced squalene hopene cyclase activity,and higher citronellal cyclase activity
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W555Y
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W555 is essential for hopene formation but W555Y and W555F have enhanced citronellal cyclase activity. All muteins of position W555 show abolished or strongly reduced hopene-forming activity compared to wild-type protein. W555Y is the only mutein with low but significant residual SHC activity
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additional information
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modification of critically located Cys residues
additional information
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various mutations of conserved amino acid residues
additional information
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mutations of Y609, Y495, Y612 and Y420 lead to an altered product pattern, compared to wild-type enzyme
additional information
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replacement of F605 by mono-, di- or trifluorophenylalanine, with or without additional mutation Y606A, kinetic analysis. Mutant F605 changed to trifluorophenylalanine plus mutation Y606A has negligibly small activity
additional information
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product patterns of mutant enzymes, detailed overview
additional information
product patterns of mutant enzymes, detailed overview
additional information
knockout of gene slr2089, phenotype and self-complementation by gene slr2089 expression
additional information
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knockout of gene slr2089, phenotype and self-complementation by gene slr2089 expression