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ATP + (2E)-hex-2-en-1-yl phosphate
ADP + (2E)-hex-2-en-1-yl diphosphate
-
-
-
-
?
ATP + (2E,6E)-farnesyl phosphate
ADP + (2E,6E)-farnesyl diphosphate
ATP + (2Z)-hex-2-en-1-yl phosphate
ADP + (2Z)-hex-2-en-1-yl diphosphate
-
-
-
-
?
ATP + 2-methylprop-2-en-1-yl phosphate
ADP + 2-methylprop-2-en-1-yl diphosphate
-
-
-
-
?
ATP + 3-bromobut-3-en-1-yl phosphate
ADP + 3-bromobut-3-en-1-yl diphosphate
-
-
-
-
?
ATP + but-2-yn-1-yl phosphate
ADP + but-2-yn-1-yl diphosphate
-
-
-
-
?
ATP + but-3-en-1-yl phosphate
ADP + but-3-en-1-yl diphosphate
ATP + but-3-yn-1-yl phosphate
ADP + but-3-yn-1-yl diphosphate
-
-
-
-
?
ATP + butyl phosphate
ADP + butyl diphosphate
ATP + dimethyl allylalcohol
ADP + dimethylallyl phosphate
very low activity
-
-
?
ATP + dimethylallyl alcohol
ADP + dimethylallyl phosphate
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
ATP + fosfomycin
ADP + ((2R,3S)-3-methyloxiran-2-yl)phosphonic phosphoric anhydride
ATP + geranyl phosphate
ADP + geranyl diphosphate
ATP + hex-5-yn-1-yl phosphate
ADP + hex-5-yn-1-yl diphosphate
-
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
ATP + isopentenyl thiolophosphate
ADP + isopentenyl thiolodiphosphate
ATP + pent-4-en-1-yl phosphate
ADP + pent-4-en-1-yl diphosphate
-
-
-
-
?
ATP + pent-4-en-2-yl phosphate
ADP + pent-4-en-2-yl diphosphate
-
-
-
-
?
ATP + pent-4-yn-1-yl phosphate
ADP + pent-4-yn-1-yl diphosphate
-
-
-
-
?
additional information
?
-
-
no substrates: geranyl monophosphate, neryl monophosphate, and farnesyl monophosphate
-
-
-
ATP + (2E,6E)-farnesyl phosphate
ADP + (2E,6E)-farnesyl diphosphate
the mutant F83A/I86A/I156A shows a 27% rate of conversion of (2E,6E)-farnesyl phosphate to (2E,6E)-farnesyl diphosphate. This reaction is not catalyzed by the wild-type enzyme
-
-
?
ATP + (2E,6E)-farnesyl phosphate
ADP + (2E,6E)-farnesyl diphosphate
the mutant F83A/I86A/I156A shows a 27% rate of conversion of (2E,6E)-farnesyl phosphate to (2E,6E)-farnesyl diphosphate. This reaction is not catalyzed by the wild-type enzyme
-
-
?
ATP + but-3-en-1-yl phosphate
ADP + but-3-en-1-yl diphosphate
low reaction rate
-
-
?
ATP + but-3-en-1-yl phosphate
ADP + but-3-en-1-yl diphosphate
low reaction rate
-
-
?
ATP + but-3-en-1-yl phosphate
ADP + but-3-en-1-yl diphosphate
-
-
-
-
?
ATP + but-3-en-1-yl phosphate
ADP + but-3-en-1-yl diphosphate
low reaction rate
-
-
?
ATP + butyl phosphate
ADP + butyl diphosphate
low reaction rate
-
-
?
ATP + butyl phosphate
ADP + butyl diphosphate
low reaction rate
-
-
?
ATP + butyl phosphate
ADP + butyl diphosphate
low reaction rate
-
-
?
ATP + dimethylallyl alcohol
ADP + dimethylallyl phosphate
molecular docking analysis indicates that dimethylallyl alcohol is a substrate for the archaeal IPK, although with low activity for thwild-type. The mutant enzymes show increased activity with dimethylallyl alcohol as substrate
-
-
?
ATP + dimethylallyl alcohol
ADP + dimethylallyl phosphate
molecular docking analysis indicates that dimethylallyl alcohol is a substrate for the archaeal IPK, although with low activity for thwild-type. The mutant enzymes show increased activity with dimethylallyl alcohol as substrate
-
-
?
ATP + dimethylallyl alcohol
ADP + dimethylallyl phosphate
molecular docking analysis indicates that dimethylallyl alcohol is a substrate for the archaeal IPK, although with low activity for the wild-type. The mutant enzymes show increased activity with dimethylallyl alcohol as substrate
-
-
?
ATP + dimethylallyl alcohol
ADP + dimethylallyl phosphate
molecular docking analysis indicates that dimethylallyl alcohol is a substrate for the archaeal IPK, although with low activity for the wild-type. The mutant enzymes show increased activity with dimethylallyl alcohol as substrate
-
-
?
ATP + dimethylallyl alcohol
ADP + dimethylallyl phosphate
molecular docking analysis indicates that dimethylallyl alcohol is a substrate for the archaeal IPK, although with low activity for the wild-type. The mutant enzymes show increased activity with dimethylallyl alcohol as substrate
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
low reaction rate
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
low reaction rate
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
low reaction rate
-
-
?
ATP + fosfomycin
ADP + ((2R,3S)-3-methyloxiran-2-yl)phosphonic phosphoric anhydride
i.e. [(2R,3S)-3-methyl-2-oxiranyl]phosphonic acid
-
-
?
ATP + fosfomycin
ADP + ((2R,3S)-3-methyloxiran-2-yl)phosphonic phosphoric anhydride
i.e. [(2R,3S)-3-methyl-2-oxiranyl]phosphonic acid
-
-
?
ATP + geranyl phosphate
ADP + geranyl diphosphate
low activity
-
-
?
ATP + geranyl phosphate
ADP + geranyl diphosphate
low reaction rate
-
-
?
ATP + geranyl phosphate
ADP + geranyl diphosphate
low reaction rate
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
the enzyme is involved in the mevalonate pathway in archaea
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
the enzyme is involved in the mevalonate pathway in archaea
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
involved in the deoxyxylulose pathway in plants
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
strictly specific for ATP, no activity with deoxyxylulose 5-phosphate, deoxyxylulose, 2-C-methylerythritol 4-phosphate
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
strictly specific for ATP
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
involved in the mevalonate pathway
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
strictly specific for ATP
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
involved in the mevalonate pathway
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
r
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?, r
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?, r
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
-
r
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
r
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
-
r
ATP + isopentenyl thiolophosphate
ADP + isopentenyl thiolodiphosphate
low reaction rate
-
-
?
ATP + isopentenyl thiolophosphate
ADP + isopentenyl thiolodiphosphate
low reaction rate
-
-
?
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ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
ATP + geranyl phosphate
ADP + geranyl diphosphate
low activity
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + dimethylallyl phosphate
ADP + dimethylallyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
the enzyme is involved in the mevalonate pathway in archaea
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
the enzyme is involved in the mevalonate pathway in archaea
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
involved in the deoxyxylulose pathway in plants
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
involved in the mevalonate pathway
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
involved in the mevalonate pathway
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
-
?
ATP + isopentenyl phosphate
ADP + isopentenyl diphosphate
-
-
-
?
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F83A/I86A/I156A
the mutant shows a 27% rate of conversion of (2E,6E)-farnesyl phosphate to (2E,6E)-farnesyl diphosphate. The reaction is not catalyzed by the wild-type enzyme
H60Q
His60 plays a key role in binding and catalysis, the mutant enzyme shows increased values for Km and decreased vaules for kcat and kcat/Km
F83A/I86A/I156A
-
the mutant shows a 27% rate of conversion of (2E,6E)-farnesyl phosphate to (2E,6E)-farnesyl diphosphate. The reaction is not catalyzed by the wild-type enzyme
-
H60Q
-
His60 plays a key role in binding and catalysis, the mutant enzyme shows increased values for Km and decreased vaules for kcat and kcat/Km
-
A53V
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme, the mutant shows increased activity compared to the wild-type enzyme
G44A
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme
G45A
site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme
G49A
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type enzyme
I140V
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
K204G
site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme
V130A
site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme
V73I
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
V73I/K204G
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
V73I/Y141V
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
V73I/Y141V/K204G
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
V73T
site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme
Y141L
site-directed mutagenesis, the mutant shows increased activity compared to the wild-type enzyme
Y141V
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
Y141V/K204G
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
K204A
kinetic values similar to wild-type
K204A
site-directed mutagenesis, the mutant shows highly increased activity compared to the wild-type enzyme
additional information
generation of two Arabidopsis T-DNA insertion lines (ipk1, ipk2) by reverse genetics. Quantitative RT-PCR (qRT-PCR) expression analysis with two sets of gene-specific primers, one located upstream of T-DNA insertions and the other downstream near the 3' end of the gene. No AtIPK transcripts are detected in ipk1, whereas transcript levels are reduced by 83% in ipk2, with remaining expression likely a result of residual splicing despite the intron-localized T-DNA insertion. Both ipk1 and ipk2 seedlings show a significant decrease in campesterol and sitosterol content (50% and 37% of wild-type, respectively), while the stigmasterol levels are unchanged
additional information
analysis and evaluation of a method of rational design that is able to identify desired mutants by analyzing the coevolution of protein sequence, use for evolving an archaeal isopentenyl phosphate kinase that can convert dimethylallyl alcohol into precursor of isoprenoids, overview. Site-directed mutagenesis of sites idetified as coevolved in the IPK family proteins
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Chen, M.; Poulter, C.D.
Characterization of thermophilic archaeal isopentenyl phosphate kinases.
Biochemistry
49
207-217
2010
Methanothermobacter thermautotrophicus (O26153), Thermoplasma acidophilum (Q9HLX1), Methanothermobacter thermautotrophicus Delta H (O26153)
brenda
Mabanglo, M.F.; Serohijos, A.W.; Poulter, C.D.
The Streptomyces-produced antibiotic fosfomycin is a promiscuous substrate for archaeal isopentenyl phosphate kinase
Biochemistry
52
917-925
2012
Streptomyces wedmorensis (Q56187), Streptomyces wedmorensis, Thermoplasma acidophilum (Q9HLX1), Thermoplasma acidophilum
brenda
Mabanglo, M.F.; Schubert, H.L.; Chen, M.; Hill, C.P.; Poulter, C.D.
X-ray structures of isopentenyl phosphate kinase
Chem. Biol.
5
517-527
2010
Methanothermobacter thermautotrophicus (O26153), Methanothermobacter thermautotrophicus, Thermoplasma acidophilum (Q9HLX1), Thermoplasma acidophilum, Methanothermobacter thermautotrophicus Delta H (O26153)
brenda
Dellas, N.; Noel, J.P.
Mutation of archaeal isopentenyl phosphate kinase highlights mechanism and guides phosphorylation of additional isoprenoid monophosphates
Chem. Biol.
5
589-601
2010
Methanocaldococcus jannaschii (Q60352), Methanocaldococcus jannaschii, Methanocaldococcus jannaschii DSM 2661 (Q60352)
brenda
Grochowski, L.L.; Xu, H.; White, R.H.
Methanocaldococcus jannaschii uses a modified mevalonate pathway for biosynthesis of isopentenyl diphosphate
J. Bacteriol.
188
3192-3198
2006
Methanocaldococcus jannaschii (Q60352), Methanocaldococcus jannaschii, Methanocaldococcus jannaschii DSM 2661 (Q60352)
brenda
Lange, B.M., Croteau R.
Isopentenyl diphosphate biosynthesis via a mevalonate-independent pathway: isopentenyl monophosphate kinase catalyzes the terminal enzymatic step
Proc. Natl. Acad. Sci. USA
96
13714-13719
1999
Mentha x piperita (P56848)
brenda
Vannice, J.C.; Skaff, D.A.; Keightley, A.; Addo, J.K.; Wyckoff, G.J.; Miziorko, H.M.
Identification in Haloferax volcanii of phosphomevalonate decarboxylase and isopentenyl phosphate kinase as catalysts of the terminal enzyme reactions in an archaeal alternate mevalonate pathway
J. Bacteriol.
196
1055-1063
2014
Haloferax volcanii (D4GWT7), Haloferax volcanii, Haloferax volcanii DSM 3757 (D4GWT7)
brenda
Henry, L.K.; Gutensohn, M.; Thomas, S.T.; Noel, J.P.; Dudareva, N.
Orthologs of the archaeal isopentenyl phosphate kinase regulate terpenoid production in plants
Proc. Natl. Acad. Sci. USA
112
10050-10055
2015
Arabidopsis thaliana (Q8H1F7)
brenda
Liu, Y.; Yan, Z.; Lu, X.; Xiao, D.; Jiang, H.
Improving the catalytic activity of isopentenyl phosphate kinase through protein coevolution analysis
Sci. Rep.
6
24117
2016
Methanocaldococcus jannaschii (Q60352), Methanocaldococcus jannaschii DSM 2661 (Q60352), Methanothermobacter thermautotrophicus (O26153), Methanothermobacter thermautotrophicus DSM 1053 (O26153), Thermoplasma acidophilum (Q9HLX1)
brenda
Yoshida, R.; Yoshimura, T.; Hemmi, H.
Reconstruction of the ''archaeal'' mevalonate pathway from the methanogenic archaeon Methanosarcina mazei in Escherichia coli cells
Appl. Environ. Microbiol.
86
1-12
2020
Methanosarcina mazei (Q8PW38), Methanosarcina mazei, Methanosarcina mazei DSM 3647 (Q8PW38)
brenda
Lund, S.; Courtney, T.; Williams, G.J.
Probing the substrate promiscuity of isopentenyl phosphate kinase as a platform for hemiterpene analogue production
ChemBioChem
20
2217-2221
2019
Thermoplasma acidophilum
brenda
McClory, J.; Timson, D.J.; Singh, W.; Zhang, J.; Huang, M.
Reaction mechanism of isopentenyl phosphate kinase A QM/MM study
J. Phys. Chem. B
121
11062-11071
2017
Thermoplasma acidophilum (Q9HLX1)
brenda