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(23E)-hydroxysqualene
rac-(2R)-2-((3aS,5aR,5bR,7aS,11aS,11bR)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-(2R)-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)prop-2-en-1-ol
-
-
-
-
?
(23E)-methylsqualene
rac-(5R,9S,10R,13R,14R,17S)-4,4,10,13,14-pentamethyl-17-((E)-6-methyloct-5-en-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene + rac-(5R,8S,9S,10R,13S,14S)-4,4,8,10,14-pentamethyl-17-((E)-6-methylocta-1,5-dien-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene + rac-(3aR,5aS,5bS,7aR,11aR,11bS,13aS)-3-(but-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysene + rac-2-((3aR,5aS,5bS,7aR,11aR,11bS,13aS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)butan-2-ol
-
-
-
-
?
(23Z)-hydroxysqualene
rac-(2R)-2-((3aS,5aR,5bR,7aS,11aS,11bR)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-(2R)-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)propanal + rac-2-((3aR,5aS,5bS,7aR,11aR,11bS)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-3-yl)prop-2-en-1-ol + ((9beta,10alpha,13xi,20xi)-20,26-epoxydammar-24-ene)
-
-
-
-
?
(23Z)-methylsqualene
(23Z)-methylsqualene + rac-(3aR,5aS,5bS,7aR,11aR,11bS,13aS)-3-(but-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysene + rac-(3aR,5aS,5bS,7aR,11aR,11bS)-3-((E)-but-2-en-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysene
-
-
-
-
?
(2E)-methylsqualene
rac-(3aR,5aS,5bS,7aR,11aR,11bS,13aS)-8-ethyl-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene
-
-
-
-
?
(2E,6E)-farnesol + geraniol
drimane-8,11-diol + [(1R,2S)-2-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]-2,6,6-trimethylcyclohexyl]methanol + 8-O-geranyl-drimane-8,11-diol + drimenol + albicanol
drimane-8,11-diol is the major product of the wild-type enzyme
-
-
?
(2E,6E)-farnesol + H2O
8-O-((2E,6E)-farnesyl)-drimane-8,11-diol + drimane-8,11-diol + drimenol + albicanol
drimane-8,11-diol is the major product of the wild-type enzyme
-
-
?
(2E,6E)-farnesol + H2O
[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]methanol + [(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol + (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol + (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2-O-((2E,6E)-farnesyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
-
-
-
?
(2E,6E)-farnesol + n-butanol
drimane-8,11-diol + drimenol + albicanol + 8-O-((2E,6E)-farnesyl)-drimane-8,11-diol + drimane-8,11-diol + farnesyl pentyl ether
drimane-8,11-diol is the major product of the wild-type enzyme
-
-
?
(3R)-2,3-oxidosqualene + H2O
3alpha-hydroxyhopene + 3alpha-hydroxyhopanol
-
-
-
?
(3S)-2,3-oxidosqualene
lanosterol
-
-
-
-
?
(3S)-2,3-oxidosqualene + H2O
3beta-hydroxyhopene + 3beta-hydroxyhopanol
-
-
-
?
(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
(-)-caparrapioxide + (-)-8-epi-caparrapioxide
-
-
-
-
?
(6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene
(4aR,5S,8aS)-1,1,4a,5,6-pentamethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aR,5S,8aS)-1,1,4a,5-tetramethyl-6-methylidenedecahydronaphthalene + (1R,2R,4aS,8aS)-1,2,5,5,8a-pentamethyldecahydronaphthalen-2-ol + (1R,2S,4aS,8aS)-1,2,5,5,8a-pentamethyldecahydronaphthalen-2-ol + (4aS,8aS)-4,4,7,8,8a-pentamethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene + (3S,4aS,8aS)-3,4,4,8,8a-pentamethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene
-
via bicyclic C8-cation
-
-
?
(E,E)-homofarnesol
(-)-ambrox + (3aS,5aS,9aS,9bS)-3a,6,6,9a-tetramethyldodeca-hydronaphtho[2,1-b]furan
-
-
-
?
(E,E,E,E)-2,6,10,14,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
8-(4,8-Dimethyl-nona-3,7-dienyl)-1,1,4a,8a-tetramethyl-7-methylene-tetradecahydro-phenanthrene
-
-
low conversion, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
1,1,4a,10a,10b-Pentamethyl-8-methylene-7-(4-methyl-pent-3-enyl)-octadecahydro-chrysene
-
-
one of the three major products, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
1,1,4a,6a,8,10a-Hexamethyl-7-(4-methyl-pent-3-enyl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydro-chrysene
-
-
one of the three major products, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
1,1,4a,8,10a,10b-Hexamethyl-7-(4-methyl-pent-3-enyl)-1,2,3,4,4a,4b,5,6,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysene
-
-
one of the three major products, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
2,4a,4b,7,7,10a-Hexamethyl-1-(4-methyl-pent-3-enyl)-octadecahydro-chrysen-2-ol
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
2-(3a,5a,5b,8,8,11a-Hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-propan-2-ol
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
alpha-3-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-icosahydro-cyclopenta[a]chrysene
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,18,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
beta-3-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-icosahydro-cyclopenta[a]chrysene
-
-
minor product, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,23-pentamethyltetracosa-2,6,10,14,18,22-hexaene
2-(5a,5b,8,8,11a-Pentamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-propan-2-ol
-
-
one of the three major products, yield 19.8%, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,23-pentamethyltetracosa-2,6,10,14,18,22-hexaene
3-Isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene
-
-
one of the three major products, yield 29.4%, NMR spectroscopic analysis
-
?
(E,E,E,E)-2,6,10,15,23-pentamethyltetracosa-2,6,10,14,18,22-hexaene
3-Isopropenyl-5a,5b,8,8,13b-pentamethyl-icosahydro-cyclopenta[a]chrysene
-
-
one of the three major products, yield 34.8%, NMR spectroscopic analysis
-
?
(E,Z)-homofarnesol
(4Z,7aS,11aS)-5,8,8,11a-tetramethyl-2,3,6,7,7a,8,9,10,11,11a-decahydrobenzo[b]oxonine + 9-epi-ambrox
-
-
-
?
(R)-citronellal + H2O
(-)-isopulegol + (+)-neoiso-isopulegol
-
-
-
-
?
(S)-6,7-epoxygeraniol + H2O
(1S,3R)-3-(hydroxymethyl)-2,2-dimethyl-4-methylidenecyclohexan-1-ol
0.57% conversion with high enzyme concentrations
-
-
?
(S)-citronellal + H2O
(+)-isopulegol
-
-
-
-
?
(S)-citronellal + H2O
(-)-iso-isopulegol
0.59% conversion with high enzyme concentrations
-
-
?
10-ethylsqualene
(2R)-2-[(7E,11E)-3-ethyl-8,12,16-trimethylheptadeca-7,11,15-trien-1-yl]-1,1-dimethyl-3-methylidenecyclohexane + (3R,5aR,9aS)-3-[(5Z)-6,10-dimethylundeca-5,9-dien-2-yl]-3-ethyl-6,6,9a-trimethyl-2,3,5,5a,6,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalene + (4aS,5R,8aR)-6-ethylidene-1,1,4a-trimethyl-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]decahydronaphthalene + (4aR,5S,8aR)-6-ethyl-1,1,4a-trimethyl-5-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]decahydronaphthalene + (2R)-2-[(3E,7E,11E)-3-ethyl-8,12,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,3,3-trimethylcyclohexanol
-
-
-
-
?
15-ethylsqualene
(2R)-2-[(3E,11E)-8-ethyl-3,12,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,1-dimethyl-3-methylidenecyclohexane + (4aS,5S,8aR)-5-[(7E)-4-ethyl-8,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a-trimethyl-6-methylidenedecahydronaphthalene + (4aS,5S,8aR)-5-[(7E)-4-ethyl-8,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (2R)-2-[(3E,11E)-8-ethyl-3,12,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,3,3-trimethylcyclohexanol
-
-
-
-
?
19-ethylsqualene
(2R)-2-[(3E,7E,11E)-12-ethyl-3,8,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,1-dimethyl-3-methylidenecyclohexane + (6R)-6-[(3E,7E,11E)-12-ethyl-3,8,16-trimethylheptadeca-3,7,11,15-tetraen-1-yl]-1,5,6-trimethylcyclohexene + (4aS,5S,8aR)-5-[(3E,7E)-8-ethyl-4,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a-trimethyl-6-methylidenedecahydronaphthalene + (5R,8R,9R,10S,14S)-4,4,8,10,14-pentamethyl-17-(7-methyloct-6-en-3-yl)-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthrene + (4aS,5S,8aR)-5-[(3E,7E)-9-ethyl-4,12-dimethyltrideca-3,7,11-trien-1-yl]-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (3S,3aS,5aR,5bR,7aR,11aS,11bS,13aR,13bS)-13b-ethyl-5a,5b,8,8,11a-pentamethyl-3-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene
-
-
-
-
?
2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)phenol + H2O
(3S,4aR,6aR,12aR,12bS)-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthen-3-ol + 2 H+
-
-
-
-
?
2-((2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienyl)phenol
(4aS,6aR,12aR,12bS)-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene + 2-[[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl]phenol + 2-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]methyl]phenol
-
-
-
-
?
2-(farnesyldimethylallyl)pyrrole
?
-
-
product is a 10:1 mixture of a tricyclic and a bicyclic unnatural polyprenoid
-
?
3,7,11-trimethyldodeca-1,6,10-trien-3-ol
(-)-caparrapioxide + (-)-8-epi-caparrapioxide
-
-
-
-
?
3-(farnesyldimethylallyl)indole
?
-
-
conversion into a 2:1 mixture of a tetracyclic and a pentacyclic product
-
?
6,7-epoxygeraniol
?
-
-
-
?
beta-pinene + H2O
alpha-pinene + terpinolene + 1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene + camphene + 2-(4-methylcyclohexa-1,3-dien-1-yl)propan-2-ol + limonene
-
-
-
?
C33 polyprene
?
-
the enzymatic products consist of mono-, bi-, tri-, tetra- and pentacyclic skeletons, however, hexacyclic products are not generated
-
-
?
citronellal + H2O
isopulegol + neo-isopulegol + iso-isopulegol
-
-
-
?
farnesol
drimenol + albicanol + driman-8,11-diol + [(1S,2R,8aS)-2,5,5,8a-tetramethyl-2-[[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy]decahydronaphthalen-1-yl]methanol
-
-
drimane-type sequiterpenes
-
?
farnesyl phenyl ether
(4aS,5S,8aS)-1,1,4a,6-tetramethyl-5-(phenoxymethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aS,4bR,10bR,12aS)-1,1,4a,10b-tetramethyl-2,3,4,4a,4b,5,10b,11,12,12a-decahydro-1H-naphtho[1,2-c]chromene
farnesylacetone
sclareoloxide
geraniol + H2O
gamma-cyclogeraniol + cyclogeraniol hydrate
0.4% conversion with high enzyme concentrations
-
-
?
geranyl phenyl ether
(6aS,10aS)-7,7,10a-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene
geranylacetone
(8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-chromene
geranylfarnesol
?
-
-
-
-
?
geranylfarnesyl acetate
?
-
-
-
-
?
geranylgeranyl phenyl ether
(14b)-8,13-dimethyl-14-(phenoxymethyl)podocarp-12-ene + (14b)-8-methyl-13-methylidene-14-(phenoxymethyl)podocarpane
-
-
-
?
homofarnesoic acid
sclareolide
hongoquercin A
?
-
-
-
-
?
hongoquercin B
?
-
-
-
-
?
squalene
hop-22(29)-ene + hopanol
squalene
hopene
-
-
-
-
?
squalene + H2O
hopan-22-ol
additional information
?
-
citronellal

isopulegol
YP3187836
activity of mutant F481C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant Y420C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant Y420C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
activity of mutant F447C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant F449C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant F438C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
wild-type enzyme, and increased activity in mutant F486C
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
activity of mutant F438C, not of the wild-type enzyme
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
wild-type enzyme, and increased activity in mutant F486C
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
citronellal
isopulegol
-
i.e. 2-isopropenyl-5-methyl-cyclohexanol
-
?
farnesyl phenyl ether

(4aS,5S,8aS)-1,1,4a,6-tetramethyl-5-(phenoxymethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aS,4bR,10bR,12aS)-1,1,4a,10b-tetramethyl-2,3,4,4a,4b,5,10b,11,12,12a-decahydro-1H-naphtho[1,2-c]chromene
-
-
-
?
farnesyl phenyl ether
(4aS,5S,8aS)-1,1,4a,6-tetramethyl-5-(phenoxymethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene + (4aS,4bR,10bR,12aS)-1,1,4a,10b-tetramethyl-2,3,4,4a,4b,5,10b,11,12,12a-decahydro-1H-naphtho[1,2-c]chromene
-
-
-
?
farnesylacetone

sclareoloxide
-
-
-
-
?
farnesylacetone
sclareoloxide
-
-
-
-
?
geranyl phenyl ether

(6aS,10aS)-7,7,10a-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene
-
-
-
?
geranyl phenyl ether
(6aS,10aS)-7,7,10a-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene
-
-
-
?
geranylacetone

(8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-chromene
-
-
-
-
?
geranylacetone
(8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-chromene
-
-
-
-
?
homofarnesoic acid

sclareolide
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?
homofarnesoic acid
sclareolide
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?
homofarnesol

ambroxan
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?
homofarnesol
ambroxan
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?
homofarnesol
ambroxan
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?
homofarnesol
ambroxan
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?
squalene

hop-22(29)-ene
YP3187836
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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hopanol is also formed
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squalene
hop-22(29)-ene
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the enzyme from Alicyclobacillus acidocaldarius yields pentacyclic hopene and hopanol (diplopterol) via a hopanyl cation from squalene
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squalene
hop-22(29)-ene
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products are formed in a molar ratio of hopene:hopanol, 5:1
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?
squalene
hop-22(29)-ene
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two types of water molecules ("front water" and "back waters") are involved around the deprotonation site. The two residues of Gln262 and Pro263 probably work to keep away the isopropyl group of the hopanyl cation intermediate from the "front water molecule", that is, to place the "front water" in a favorable position, leading to the minimal production of by-products, i.e., hopanol and hop-21(22)-ene. The five residues of Thr41, Glu45, Glu93, Arg127 and Trp133, by which the hydrogen-bonded network incorporating the "back waters" is constructed, increase the polarization of the "front water" to facilitate proton elimination from the isopropyl moiety of the hopanyl cation, leading to the normal product, hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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products are formed in a molar ratio of hopene:hopanol, 5:1
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
Q81YD8
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene
hop-22(29)-ene
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?
squalene

hop-22(29)-ene + hopanol
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the enzyme catalyzes cyclization of the linear triterpenoid squalene to hopene and hopanol by the class II mechanism
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?
squalene
hop-22(29)-ene + hopanol
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?
squalene
hop-22(29)-ene + hopanol
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the enzyme catalyzes cyclization of the linear triterpenoid squalene to hopene and hopanol by the class II mechanism
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?
squalene
hop-22(29)-ene + hopanol
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?
squalene + H2O

hopan-22-ol
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squalene + H2O
hopan-22-ol
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?
squalene + H2O
hopan-22-ol
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?
squalene + H2O
hopan-22-ol
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?
additional information

?
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YP3187836
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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substrate specificity, overview
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?
additional information
?
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substrate specificity, overview
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?
additional information
?
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mutations lead to altered product pattern
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?
additional information
?
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mutations lead to altered product pattern
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?
additional information
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mutations lead to altered product pattern
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?
additional information
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mutations lead to altered product pattern
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?
additional information
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overview of cyclization products of wild type and mutant enzymes
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?
additional information
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overview of cyclization products of wild type and mutant enzymes
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?
additional information
?
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(E,E,E,E)-2,6,11,14,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene: no detectable enzymatic activity
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?
additional information
?
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no enzymatic cyclization of 3-(geranylgeranyl)indole
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?
additional information
?
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no substrate: 2-(geranylgeranyl)pyrrole
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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enzyme substrate specificity in polycyclization reactions, overview
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?
additional information
?
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no activity with linalool and pseudoionone
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?
additional information
?
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the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
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?
additional information
?
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the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
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?
additional information
?
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the enzyme shows substrate diversity for polycyclization reactions, since squalene-hopene cyclases specifically address and protonate terminal double bonds of linear terpenoids, molecules with functional groups like carboxylic acids or amides can be used as substrates, overview. It is active with squalene, a C-35 squalene analogue substrate, farnesol, and geranyl geraniol, but not with geraniol, products overview
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?
additional information
?
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product pattern of alternative substrates, overview
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?
additional information
?
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product pattern of alternative substrates, overview
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?
additional information
?
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no activity with 6-ethylsqualene
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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no activity with geraniol
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?
additional information
?
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Q81YD8
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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the enzyme does not catalyze 2,3-oxidosqualene cyclization nor tetrahymanol formation. Substrate specificity, detailed overview
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?
additional information
?
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no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
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?
additional information
?
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the enzyme does not catalyze tetrahymanol formation. Substrate specificity, detailed overview