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IUBMB Comments Isolated from the plant Zea mays (maize). The product is named in the reference using a different numbering scheme for eudesmane.
Synonyms
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maize eudesmanediol synthase
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ZmEDS
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(2E,6E)-farnesyl diphosphate + 2 H2O = 7-epi-ent-eudesmane-5,11-diol + diphosphate
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(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, 7-epi-ent-eudesmane-5,11-diol-forming)
Isolated from the plant Zea mays (maize). The product is named in the reference using a different numbering scheme for eudesmane.
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(2E,6E)-farnesyl diphosphate + 2 H2O
7-epi-ent-eudesmane-5,11-diol + diphosphate
(2E,6E)-farnesyl diphosphate + 2 H2O
alpha-eudesmol + 10-epi-gamma-eudesmol + elemol + diphosphate
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Substrates: -
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(2E,6E)-farnesyl diphosphate + 2 H2O
7-epi-ent-eudesmane-5,11-diol + diphosphate
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Substrates: -
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(2E,6E)-farnesyl diphosphate + 2 H2O
7-epi-ent-eudesmane-5,11-diol + diphosphate
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Substrates: 7-epi-ent-eudesmane-5,11-diol i.e. (4S,4aS,6R,8aS)-6-(2-hydroxypropan-2-yl)-4,8a-dimethyldecahydronaphthalen-4a-ol
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(2E,6E)-farnesyl diphosphate + 2 H2O
7-epi-ent-eudesmane-5,11-diol + diphosphate
Substrates: -
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(2E,6E)-farnesyl diphosphate + 2 H2O
7-epi-ent-eudesmane-5,11-diol + diphosphate
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Substrates: -
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UniProt
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ZmEDS is specifically expressed in roots
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Highest Expressing Human Cell Lines
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Cell Line Links
Gene Links
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metabolism
the configuration at C7 in the eudesmol-3-yl+ intermediate formed by protonation-initiated (bi)cyclization dictates the further course of the catalyzed reaction. If the 2,7-ring closure occurs via addition to the re face of the 6,7-olefin, that generates the 7alpha-methyl (Me) epimer of eudesmol-3-yl+, with the final product eudesmanediol. If (bi)cyclization occurs via addition to the si face of the 6,7-olefin, that generates the 7beta-methyl epimer of eudesmol-3-yl+. This then generally undergoes direct deprotonation to generate a eudesmol derived olefin. Addition of water can also occur, generating the alternative diol products 3-epi-cryptomeridiol and 2,3-epi-cryptomeridiol
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EDSB_MAIZE
557
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63294
Swiss-Prot
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EDSM_MAIZE
557
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63237
Swiss-Prot
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apo-form, to 1.83 A resolution, space group P6122
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F299L
mutant primarily produces a mixture of alpha- and beta-eudesmol
F303A
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mutant enzyme shows predominant production of hedycarol
F303L
mutant primarily produces a mixture of alpha- and beta-eudesmol, both derived from protonation initiated (bi)cyclization of hedycaryol
G411A
mutant generates almost no diols, instead predominantly produces valerianol. Production of valerianol requires a 1,2-methyl shift in the eudesmolyl+ intermediate prior to direct deprotonation
I279G
mutant primarily generates 3-epi-cryptomeridiol. Residues I279 and V306 are important for the 1,2-hydride shift, as well as affecting which face of the carbocation the (second) water is added to
N453D
mutant efficiently produces almost exclusively hedycaryol
S410G
mutant only generates higher amounts of alpha- and beta-eudesmol
S410T
mutation does not significantly change the observed product profile
T409G
mutation leads to a significant decrease in diol products, with corresponding increase in hedycaryol, as well as alpha- and beta-eudesmol
T409S
mutation does not significantly change the observed product profile
V306A
mutant generates 2,3-epi-cryptomeridiol as its main diol product. V306A also generates eremophil-1(10)-en-11-ol. This requires the 1,2-hydride shift also necessary for generation of eudesmanediol, but also a 1,2-methyl shift to form the eremophilol backbone, as well as subsequent 1,4-hydride shift. Residues I279 and V306 are important for the 1,2-hydride shift, as well as affecting which face of the carbocation the (second) water is added to
Y529F
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while the ZmEDS:Y529F mutant produces an increased amount of hedycaryol the other products, including the sesquiterpenoid diols, are still present
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54.2
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melting temperature
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expressed in Escherichia coli
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expressed in leaves of Nicotiana benthamiana
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infection with the fungal pathogen Fusarium verticillioides significantly induces accumulation of ZmEDS transcripts in roots
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Liang, J.; Liu, J.; Brown, R.; Jia, M.; Zhou, K.; Peters, R.; Wang, Q.
Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase
Plant J.
94
847-856
2018
Zea mays
brenda
Liang, J.; Wang, L.; Liu, J.; Shen, Q.; Fu, J.; Peters, R.J.; Wang, Q.
Probing enzymatic structure and function in the dihydroxylating sesquiterpene synthase ZmEDS
Biochemistry
59
2660-2666
2020
Zea mays (A0A1D6EFT8)
brenda
Kracht, O.N.; Correia Cordeiro, R.S.; Hakansson, M.; Stockmann, J.; Sander, D.; Bandow, J.; Senges, C.H.R.; Logan, D.T.; Kourist, R.
Discovery of three novel sesquiterpene synthases from Streptomyces chartreusis NRRL 3882 and crystal structure of an alpha-eudesmol synthase
J. Biotechnol.
297
71-77
2019
Streptomyces chartreusis NRRL 3882
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