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Information on EC 5.4.99.17 - squalene-hopene cyclase
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EC Tree
5.4.99.17 squalene-hopene cyclaseIUBMB Comments
The enzyme also produces the cyclization product hopan-22-ol by addition of water (cf. EC 4.2.1.129, squalene-hopanol cyclase). Hopene and hopanol are formed at a constant ratio of 5:1.
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Word Map
- 5.4.99.17
-
cyclization
- acidocaldarius
- alicyclobacillus
- cyclases
- oxidosqualene
-
hopanoids
-
pentacyclic
-
triterpene
- 2,3-oxidosqualene
-
tetracyclic
-
carbocation
- lanosterol
-
5.4.99.7
-
aspartate-rich
-
polyolefinic
- synthesis
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
AacSHC, cyclase, squalene-hopanoid, SHC, SHC1, SHC2, Spterp25, SQ-hopene cyclase, squalene hopene cyclase, squalene-hopene cyclase, ZmoSHC1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
SHC
SHC1
SHC2
SQ-hopene cyclase
squalene hopene cyclase
squalene-hopene cyclase
ZmoSHC1
ZmSHC1
SHC
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
squalene + H2O = hopan-22-ol
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-
-
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squalene = hop-22(29)-ene
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-
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squalene = hop-22(29)-ene
catalytic mechanism via Friedel-Crafts alkylation and substrate specificity, overview
squalene = hop-22(29)-ene
catalytic mechanism, the initial reaction catalyzed is the protonation of the terminal double bond of squalene. The conserved DXDD motif of SHCs is essential for this protonation reaction, overview
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squalene = hop-22(29)-ene
catalytic mechanism, the initial reaction catalyzed is the protonation of the terminal double bond of squalene. The conserved DXDD motif of SHCs is essential for this protonation reaction, overview
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squalene = hop-22(29)-ene
catalytic mechanism, the initial reaction catalyzed is the protonation of the terminal double bond of squalene. The conserved DXDD motif of SHCs is essential for this protonation reaction, overview
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squalene = hop-22(29)-ene
catalytic mechanism, the initial reaction catalyzed is the protonation of the terminal double bond of squalene. The conserved DXDD motif of SHCs is essential for this protonation reaction, overview
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squalene = hop-22(29)-ene
catalytic mechanism, the initial reaction catalyzed is the protonation of the terminal double bond of squalene. The conserved DXDD motif of SHCs is essential for this protonation reaction, overview
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squalene = hop-22(29)-ene
catalytic mechanism, the initial reaction catalyzed is the protonation of the terminal double bond of squalene. The conserved DXDD motif of SHCs is essential for this protonation reaction, overview
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squalene = hop-22(29)-ene
catalytic mechanism, the initial reaction catalyzed is the protonation of the terminal double bond of squalene. The conserved DXDD motif of SHCs is essential for this protonation reaction. In Alicyclobacillus acidocaldarius SHC, Asp376 of this motif is hydrogen bonded to His451, and an additional hydrogen bond exists to an ordered water molecule, which connects D376 to the hydroxyl group of the Y495 side chain and thus further enhances its acidity. The carboxyl groups of Asp374 and Asp377 accommodate the positive charge of the D376-H451 pair prior to proton transfer. After proton transfer to the 2,3-double bond of squalene, the D376-H451 pair loses its charge, leaving the remaining negative charge on the D374-D377 pair for stabilization of the initial cationic intermediates (24, 101). Reprotonation of D376 occurs through a water molecule bound to Y495-OH, which can transfer protons from disordered water in the solvent-accessible upper cavity of SHC
squalene = hop-22(29)-ene
overall mechanism of the polycyclization reaction of SHCs and structures of squalene cyclization products, overview
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squalene = hop-22(29)-ene
overall mechanism of the polycyclization reaction of SHCs and structures of squalene cyclization products, overview
squalene = hop-22(29)-ene
catalytic mechanism via Friedel-Crafts alkylation and substrate specificity, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyclization
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SYSTEMATIC NAME
IUBMB Comments
squalene mutase (cyclizing)
The enzyme also produces the cyclization product hopan-22-ol by addition of water (cf. EC 4.2.1.129, squalene-hopanol cyclase). Hopene and hopanol are formed at a constant ratio of 5:1.
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CAS REGISTRY NUMBER
COMMENTARY
76600-69-6
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(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
(2E,6E)-farnesol + H2O
8-O-((2E,6E)-farnesyl)-drimane-8,11-diol + drimane-8,11-diol + drimenol + albicanol
(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
(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
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via bicyclic C8-cation
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-
?
(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
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-
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
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-
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
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one of the three major products, NMR spectroscopic analysis
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?
(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
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one of the three major products, NMR spectroscopic analysis
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?
(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
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minor product, NMR spectroscopic analysis
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?
(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
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minor product, NMR spectroscopic analysis
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?
(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
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minor product, NMR spectroscopic analysis
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?
(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
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minor product, NMR spectroscopic analysis
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?
(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
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one of the three major products, yield 19.8%, NMR spectroscopic analysis
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?
(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
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one of the three major products, yield 29.4%, NMR spectroscopic analysis
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?
(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
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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
(-)-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
?
-
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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
?
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-
conversion into a 2:1 mixture of a tetracyclic and a pentacyclic product
-
?
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
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
geranylgeranyl phenyl ether
(14b)-8,13-dimethyl-14-(phenoxymethyl)podocarp-12-ene + (14b)-8-methyl-13-methylidene-14-(phenoxymethyl)podocarpane
-
-
-
?
(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 + 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
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 + 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
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
(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
-
-
?
(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
-
-
-
?
(3R)-2,3-oxidosqualene + H2O
3alpha-hydroxyhopene + 3alpha-hydroxyhopanol
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
(3S)-2,3-oxidosqualene + H2O
3beta-hydroxyhopene + 3beta-hydroxyhopanol
-
-
-
?
(3S)-2,3-oxidosqualene + H2O
3beta-hydroxyhopene + 3beta-hydroxyhopanol
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
(E,E)-homofarnesol
(-)-ambrox + (3aS,5aS,9aS,9bS)-3a,6,6,9a-tetramethyldodeca-hydronaphtho[2,1-b]furan
-
-
-
?
(E,E)-homofarnesol
(-)-ambrox + (3aS,5aS,9aS,9bS)-3a,6,6,9a-tetramethyldodeca-hydronaphtho[2,1-b]furan
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
(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
-
-
-
?
(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
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
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
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
-
-
-
?
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
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
the enzyme from Alicyclobacillus acidocaldarius yields pentacyclic hopene and hopanol (diplopterol) via a hopanyl cation from squalene
-
?
squalene
hop-22(29)-ene
-
products are formed in a molar ratio of hopene:hopanol, 5:1
-
-
?
squalene
hop-22(29)-ene
-
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
-
-
?
squalene
hop-22(29)-ene
-
products are formed in a molar ratio of hopene:hopanol, 5:1
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
squalene
hop-22(29)-ene + hopanol
-
the enzyme catalyzes cyclization of the linear triterpenoid squalene to hopene and hopanol by the class II mechanism
-
-
?
squalene
hop-22(29)-ene + hopanol
-
the enzyme catalyzes cyclization of the linear triterpenoid squalene to hopene and hopanol by the class II mechanism
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
additional information
?
-
YP3187836
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
substrate specificity, overview
-
-
?
additional information
?
-
substrate specificity, overview
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
mutations lead to altered product pattern
-
-
?
additional information
?
-
-
overview of cyclization products of wild type and mutant enzymes
-
-
?
additional information
?
-
-
overview of cyclization products of wild type and mutant enzymes
-
-
?
additional information
?
-
-
(E,E,E,E)-2,6,11,14,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene: no detectable enzymatic activity
-
-
?
additional information
?
-
-
no enzymatic cyclization of 3-(geranylgeranyl)indole
-
-
?
additional information
?
-
-
no substrate: 2-(geranylgeranyl)pyrrole
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
enzyme substrate specificity in polycyclization reactions, overview
-
-
?
additional information
?
-
-
no activity with linalool and pseudoionone
-
-
?
additional information
?
-
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
product pattern of alternative substrates, overview
-
-
?
additional information
?
-
product pattern of alternative substrates, overview
-
-
?
additional information
?
-
-
no activity with 6-ethylsqualene
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with geraniol
-
-
?
additional information
?
-
Alicyclobacillus acidocaldarius subsp. DSM 446
no activity with geraniol
-
-
?
additional information
?
-
Q81YD8
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, but no tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
Burkholderia ambifaria ATCC BAA-244 / AMMD
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
Burkholderia ambifaria ATCC BAA-244 / AMMD
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme does not catalyze 2,3-oxidosqualene cyclization nor tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme does not catalyze tetrahymanol formation. Substrate specificity, detailed overview
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
hydroxysqualene is a poor substrate
-
-
?
additional information
?
-
-
hydroxysqualene is a poor substrate
-
-
?
additional information
?
-
-
substrate specificity, detailed overview
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
the enzyme also catalyzes 2,3-oxidosqualene cyclization, substrate specificity, detailed overview
-
-
?
additional information
?
-
-
enzyme produces a wide variety of products due to lack of specificity
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with linalool and pseudoionone
-
-
?
additional information
?
-
-
substrate specificity, detailed overview
-
-
?
additional information
?
-
substrate specificity, overview. No activity with prenyl phenyl ether
-
-
?
additional information
?
-
ZmoSHC1 shows cyclization of the non-natural substrates homofarnesol (C16) and citronellal (C10) in addition to hopene formation from squalene, substrate specificity, overview. ZmoSHC1 exhibits a shift of activity towards substrates of shorter chain lengths, displaying over 50fold higher conversion of homofarnesol and more than 2fold higher conversion of citronellal in comparison to squalene conversion
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
ZmoSHC1 shows cyclization of the non-natural substrates homofarnesol (C16) and citronellal (C10) in addition to hopene formation from squalene, substrate specificity, overview. ZmoSHC1 exhibits a shift of activity towards substrates of shorter chain lengths, displaying over 50fold higher conversion of homofarnesol and more than 2fold higher conversion of citronellal in comparison to squalene conversion
-
-
?
additional information
?
-
substrate specificity, overview. No activity with prenyl phenyl ether
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
-
?
squalene
hop-22(29)-ene
-
-
-
-
?
squalene
hop-22(29)-ene
-
-
-
?
squalene
hop-22(29)-ene
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
-
-
-
?
squalene + H2O
hopan-22-ol
Alicyclobacillus acidocaldarius subsp. DSM 446
-
-
-
?
additional information
?
-
YP3187836
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
product pattern of alternative substrates, overview
-
-
?
additional information
?
-
product pattern of alternative substrates, overview
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
Q81YD8
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
Burkholderia ambifaria ATCC BAA-244 / AMMD
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
Burkholderia ambifaria ATCC BAA-244 / AMMD
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?
additional information
?
-
no activity with citronellal or isopulegol (2-isopropenyl-5-methyl-cyclohexanol)
-
-
?