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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

Reaction

squalene
+
H2O
=
hopan-22-ol

Synonyms

AacSHC, cyclase, squalene-hopanoid, SHC, SHC1, SHC2, Spterp25, SQ-hopene cyclase, squalene hopene cyclase, squalene-hopene cyclase, ZmoSHC1, ZmSHC1

ECTree

     5 Isomerases
         5.4 Intramolecular transferases
             5.4.99 Transferring other groups
                5.4.99.17 squalene-hopene cyclase

Engineering

Engineering on EC 5.4.99.17 - squalene-hopene cyclase

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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
F481C
YP3187836
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
C25S/C50S/C435S/C455S/C537S
-
quintuple mutant
C25S/C50S/D376C/C435S/C455S/C537S
-
sextuple mutant
C435S/D374I/D374V/H451F
D376C
D376E
D376E/D377E
-
no enzyme activity
D376G
-
0.2% activity when enzyme concentration is increased to 100fold
D376Q
-
no enzyme activity
D376R
-
no enzyme activity
D377C/D377N/Y612A
D377C/V380E/V381A
-
no detectable cyclization of squalene
D377E
-
0.2% activity when enzyme concentration is increased to 100fold
D377E/D376Q/D376R/D377R/E45K/W406V/W417A/D377C
D377G
-
0.2% activity when enzyme concentration is increased to 100fold
D377Q
-
0.2% activity when enzyme concentration is increased to 100fold
D377R
-
no enzyme activity
E45D
-
reduced enzyme activity
E45K
-
no enzyme activity
E45Q
-
slightly increased enzyme activity
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
-
and mutant with F365 changed to unnatural amino acid O-methyltyrosine. Both show increased decreased activity at high temperature
F434A
F437A
F601A
F601W
the mutant shows about wild type activity
F605A
F605W
-
increased catalytic acitivy at low temperature, but decreased activity at high temperature due to higher cation-pi binding energies
F605Y
-
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
-
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
-
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
V380E
V381A/D376C
W133A
W169A
W169F/W169H/W489A/F605K
W23V
-
same activity and optimal temperature as wild type enzyme
W258L
-
60% of wild type activity, lower temperature optimum
W312G
-
the mutant produces (-)-neo-isopulegol from (S)-citronellal
W406V
-
no enzyme activity
W417A
-
no enzyme activity
W485V
-
same activity and optimal temperature as wild type enzyme
W522V
-
same activity and optimal temperature as wild type enzyme
W533A
-
same activity and optimal temperature as wild type enzyme
W591L
-
same activity and optimal temperature as wild type enzyme
W78S
-
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
Y495F
-
reduced enzyme activity, wild-type product pattern
Y606A
-
kinetics identical to wild-type
Y606A/W23V/W495V/W522V/W533A/W591L/W78S/E35Q/E197Q/D530N/T378A
Y609A
-
the mutant produces (+)-isopulegol from (S)-citronellal
Y609A/Y612A/L607K
Y609F
Y612F
-
reduced enzyme activity, wild-type product pattern
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
-
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
-
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
-
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
-
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
-
F450C
Burkholderia ambifaria ATCC BAA-244 / AMMD
-
site-directed mutagenesis, the mutant does not perform interconversion of citronellal and isopulegol
-
F445C
-
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
-
site-directed mutagenesis, the mutant performs interconversion of citronellal and isopulegol
-
F486C
-
site-directed mutagenesis, the mutant shows increased activity in interconversion of citronellal and isopulegol compared to the wild-type enzyme
-
W555F
W555Y
additional information