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Information on EC 4.2.3.163 - (+)-corvol ether B synthase
for references in articles please use BRENDA:EC4.2.3.163
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EC Tree 4 Lyases
4.2 Carbon-oxygen lyases
4.2.3 Acting on phosphates
4.2.3.163 (+)-corvol ether B synthase
IUBMB Comments
The enzyme, which forms the sesquiterpene (+)-corvol ether B, has been reported from the bacterium Kitasatospora setae.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
showSynonyms
KSE_12950, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
KSE_12950
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate + H2O = (+)-corvol ether B + diphosphate
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [cyclizing, (+)-corvol ether B-forming]
The enzyme, which forms the sesquiterpene (+)-corvol ether B, has been reported from the bacterium Kitasatospora setae.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: (+)-corvol ether B i.e. (3R,5aR,6S,8aR)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine. No activity with geranylgeranyl diphosphate. The enzyme forms (+)-corvol ether B and (+)-corvol ether A in the ratio of 3:1
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: (+)-corvol ether B i.e. (1S*,3R*,5aR*,6S*,8aR*)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine, corvol ether is formed through reprotonation of the neutral intermediate
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: no activity with geranylgeranyl diphosphate. The enzyme forms (+)-corvol ether B and (+)-corvol ether A in the ratio of 3:1. Quantum chemical calculations reveal that a sequence of two 1,2-hydride migrations in the cyclisation cascade from (2E,6E)-farnesyl diphosphate to the corvol ethers A and B are energetically more favourable than an alternative pathway through one 1,3-hydride shift. Because these calculations do not give any insights into what extent the relevant intermediate cations in the two hypothetical cyclisation reactions might be stabilised by the terpene cyclase, isotopic labelling experiments are performed. These pointed to the same enzyme mechanism, thus giving evidence for a cyclisation mechanism through two 1,2-hydride shifts
Products: (+)-corvol ether B i.e. (1S*,3R*,5aR*,6S*,8aR*)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine
Products: (+)-corvol ether B i.e. (1S*,3R*,5aR*,6S*,8aR*)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
-
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: (+)-corvol ether B i.e. (3R,5aR,6S,8aR)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine. No activity with geranylgeranyl diphosphate. The enzyme forms (+)-corvol ether B and (+)-corvol ether A in the ratio of 3:1
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: (+)-corvol ether B i.e. (1S*,3R*,5aR*,6S*,8aR*)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine, corvol ether is formed through reprotonation of the neutral intermediate
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: no activity with geranylgeranyl diphosphate. The enzyme forms (+)-corvol ether B and (+)-corvol ether A in the ratio of 3:1. Quantum chemical calculations reveal that a sequence of two 1,2-hydride migrations in the cyclisation cascade from (2E,6E)-farnesyl diphosphate to the corvol ethers A and B are energetically more favourable than an alternative pathway through one 1,3-hydride shift. Because these calculations do not give any insights into what extent the relevant intermediate cations in the two hypothetical cyclisation reactions might be stabilised by the terpene cyclase, isotopic labelling experiments are performed. These pointed to the same enzyme mechanism, thus giving evidence for a cyclisation mechanism through two 1,2-hydride shifts
Products: (+)-corvol ether B i.e. (1S*,3R*,5aR*,6S*,8aR*)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine
Products: (+)-corvol ether B i.e. (1S*,3R*,5aR*,6S*,8aR*)-3,6-dimethyl-1-(propan-2-yl)hexahydro-1H,3H-3,8a-methanocyclopenta[c]oxepine
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: incubation of the purified enzyme with geranyl diposphate yields small amounts of several acyclic and cyclic monoterpenes, with linalool as the main product
Products: -
Products: -
?
additional information
?
-
Substrates: incubation of the purified enzyme with geranyl diposphate yields small amounts of several acyclic and cyclic monoterpenes, with linalool as the main product
Products: -
Products: -
?
additional information
?
-
Substrates: incubation of the purified enzyme with geranyl diposphate yields small amounts of several acyclic and cyclic monoterpenes, with linalool as the main product
Products: -
Products: -
?
additional information
?
-
Substrates: incubation of the purified enzyme with geranyl diposphate yields small amounts of several acyclic and cyclic monoterpenes, with linalool as the main product
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
-
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
Substrates: -
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-corvol ether B + diphosphate
-
Substrates: -
Products: -
Products: -
?
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). BTPSL_METGA
Metarhizium guizhouense (strain ARSEF 977)
348
0
39569
Swiss-Prot
other Location (Reliability: 5)
BTPSL_METMF
Metarhizium majus (strain ARSEF 297)
355
0
40204
Swiss-Prot
-
BTPS2_METBS
Metarhizium brunneum (strain ARSEF 3297)
342
0
38824
Swiss-Prot
-
BTPS1_METBS
Metarhizium brunneum (strain ARSEF 3297)
332
0
37835
Swiss-Prot
other Location (Reliability: 2)
CEABS_KITSK
Kitasatospora setae (strain ATCC 33774 / DSM 43861 / JCM 3304 / KCC A-0304 / NBRC 14216 / KM-6054)
320
0
36227
Swiss-Prot
-
BTPSL_METAQ
Metarhizium acridum (strain CQMa 102)
349
0
39947
Swiss-Prot
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
cloned into pYE-Express, a pET28-derived plasmid that can be used for efficient cloning by homologous recombination in yeast and for heterologous expression of His-tagged recombinant enzymes in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
analysis
-
PMAs and EIMS fragmentation mechanisms for the fragment ions of reaction product
analysis
-
PMAs and EIMS fragmentation mechanisms for the fragment ions of reaction product
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Rabe, P.; Pahirulzaman, K.A.; Dickschat, J.S.
Structures and biosynthesis of corvol ethers-sesquiterpenes from the actinomycete Kitasatospora setae
Angew. Chem. Int. Ed. Engl.
54
6041-6045
2015
Kitasatospora setae (E4N7E5), Kitasatospora setae DSM 43861 (E4N7E5)
brenda
Rinkel, J.; Rabe, P.; Garbeva, P.; Dickschat, J.S.
Lessons from 1,3-hydride shifts in sesquiterpene cyclizations
Angew. Chem. Int. Ed. Engl.
55
13593-13596
2016
Kitasatospora setae (E4N7E5), Kitasatospora setae DSM 43861 (E4N7E5)
brenda
Rabe, P.; Janusko, A.; Goldfuss, B.; Dickschat, J.S.
Experimental and theoretical studies on corvol ether biosynthesis
Chembiochem
17
146-149
2016
Kitasatospora setae (E4N7E5), Kitasatospora setae DSM 43861 (E4N7E5)
brenda
Rabe, P.; Dickschat, J.S.
The EIMS fragmentation mechanisms of the sesquiterpenes corvol ethers A and B, epi-cubebol and isodauc-8-en-11-ol
Beilstein J. Org. Chem.
12
1380-1394
2016
Kitasatospora setae, Kitasatospora setae DSM 43861
brenda
EXTERNAL LINKS (specific for EC-Number 4.2.3.163)
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