Information on EC 2.5.1.59 - protein geranylgeranyltransferase type I

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.5.1.59
-
RECOMMENDED NAME
GeneOntology No.
protein geranylgeranyltransferase type I
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranylgeranyl diphosphate + protein-cysteine = S-geranylgeranyl-protein + diphosphate
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
geranylgeranyl-diphosphate:protein-cysteine geranyltransferase
This enzyme, along with protein farnesyltransferase (EC 2.5.1.58) and protein geranylgeranyltransferase type II (EC 2.5.1.60), constitutes the protein prenyltransferase family of enzymes. Catalyses the formation of a thioether linkage between the C-1 atom of the geranylgeranyl group and a cysteine residue fourth from the C-terminus of the protein. These protein acceptors have the C-terminal sequence CA1A2X, where the terminal residue, X, is preferably leucine; serine, methionine, alanine or glutamine makes the protein a substrate for EC 2.5.1.58. The enzymes are relaxed in specificity for A1, but cannot act if A2 is aromatic. Known targets of this enzyme include most gamma-subunits of heterotrimeric G proteins and Ras-related GTPases such as members of the Ras and Rac/Rho families. A zinc metalloenzyme. The Zn2+ is required for peptide, but not for isoprenoid, substrate binding.
CAS REGISTRY NUMBER
COMMENTARY hide
135371-29-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain SC5314
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Uniprot
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3,7,11-trimethyl-12-(7-nitro-benzo[1,2,5]-oxadiazo-4-ylamino)-dodeca-2,6,10-trien-1-diphosphate + GST-RhoA
diphosphate + ?
show the reaction diagram
-
-
-
-
?
3,7-dimethyl-8-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-octa-2,6-diene-1-diphosphate + GST-RhoA
diphosphate + ?
show the reaction diagram
-
-
-
-
?
farnesyl diphosphate + (biotin-CONH-(CH2)5-CO-)-NPFREKKFFCAI-Leu
diphosphate + (biotin-CONH-(CH2)5-CO-)-NPFREKKFF-S-farnesyl-CAI-Leu
show the reaction diagram
farnesyl diphosphate + Ki-Ras4B
diphosphate + S-geranylgeranyl-Ki-Ras4B
show the reaction diagram
-
-
-
-
?
farnesyl diphosphate + protein-cysteine
S-farnesyl protein + diphosphate
show the reaction diagram
geranylgeranyl diphosphate + (biotin-CONH-(CH2)5-CO-)-ALEPPETEPKRKCCI-Phe
diphosphate + (biotin-CONH-(CH2)5-CO-)-ALEPPETEPKRK-S-geranylgeranyl-CCI-Phe
show the reaction diagram
geranylgeranyl diphosphate + (biotin-CONH-(CH2)5-CO-)-GTPRASNRSCAIS
diphosphate + (biotin-CONH-(CH2)5-CO-)-GTPRASNRS-S-geranylgeranyl-CAIS
show the reaction diagram
-
ECB-laminB(S), 5% activity in comparison of protein substrate motif: CAA-leucine
-
-
?
geranylgeranyl diphosphate + (biotin-CONH-(CH2)5-CO-)-NPFREKKFFCAI-Leu
diphosphate + (biotin-CONH-(CH2)5-CO-)-NPFREKKFF-S-geranylgeranyl-CAI-Leu
show the reaction diagram
geranylgeranyl diphosphate + Arg-Arg-Cys-Val-Leu-Leu
diphosphate + Arg-Arg-S-geranylgeranyl-Cys-Val-Leu-Leu
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Asp-Asp-Pro-Thr-Ala-Ser-Ala-Cys-Val-Leu-Leu
Asp-Asp-Pro-Thr-Ala-Ser-Ala-(S-geranylgeranyl)-Cys-Val-Leu-Leu + diphosphate
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Cys-Val-Leu-Leu
S-geranylgeranyl-Cys-Val-Leu-Leu + diphosphate
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Cys-Val-Leu-Ser
S-geranylgeranyl-Cys-Val-Leu-Ser + diphosphate
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + dansyl-Cys-Ile-Ile-Leu
diphosphate + dansyl-S-geranylgeranyl-Cys-Ile-Ile-Leu
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + dansyl-Thr-Lys-Cys-Val-Ile-Met
diphosphate + dansyl-Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Met
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + glutathione S-transferase-GCVKIKKCVIL
diphosphate + ?
show the reaction diagram
geranylgeranyl diphosphate + GST-CDC42
diphosphate + GST-S-geranylgeranyl-CDC42
show the reaction diagram
-
recombinant glutathione S-transferase fusion protein of CDC42Hs with a C-terminal Cys-Cys-Ile-Phe sequence
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-
?
geranylgeranyl diphosphate + GST-RhoA
diphosphate + GST-S-geranylgeranyl-RhoA
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + H-Ras-CVLL
S-geranylgeranyl-protein + ?
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + Ki-Ras4A
diphosphate + S-geranylgeranyl-Ki-Ras4A
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + Ki-Ras4B
diphosphate + S-geranylgeranyl-Ki-Ras4B
show the reaction diagram
geranylgeranyl diphosphate + Leu-Pro-Cys-Val-Val-Met
diphosphate + Leu-Pro-S-geranylgeranyl-Cys-Val-Val-Met
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + Lys-Lys-Cys-Ile-Ile-Met
diphosphate + Lys-Lys-S-geranylgeranyl-Cys-Ile-Ile-Met
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + N-dansyl-Gly-Cys-Val-Ile-Leu-OH
?
show the reaction diagram
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geranylgeranyl diphosphate + N-Ras
diphosphate + S-geranylgeranyl-N-Ras
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Phe-Phe-Cys-Ala-Ile-Leu
diphosphate + Phe-Phe-S-geranylgeranyl-Cys-Ala-Ile-Leu
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + protein-cysteine
S-geranylgeranyl protein + diphosphate
show the reaction diagram
-
the enzyme catalyzes posttranslational modification of proteins, the farnesyl moieties attached to the substrates are direcly involved in protein-protein interactions as well as in protein-membrane interactions
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-
?
geranylgeranyl diphosphate + protein-cysteine
S-geranylgeranyl-protein + diphosphate
show the reaction diagram
geranylgeranyl diphosphate + Ras protein
S-geranylgeranyl-Ras protein + diphosphate
show the reaction diagram
geranylgeranyl diphosphate + Ras-CVLL
S-geranylgeranyl-Ras-CVLL + diphosphate
show the reaction diagram
-
tritium labelled geranylgeranyl diphosphate for enzyme assay, His-tagged geranylgeranyl diphosphate
-
-
?
geranylgeranyl diphosphate + Ras-Cys-Val-Leu-Leu
diphosphate + Ras-S-geranylgeranyl-Cys-Val-Leu-Leu
show the reaction diagram
geranylgeranyl diphosphate + RhoA
diphosphate + S-geranylgeranyl-RhoA
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + rhoC protein
S-geranylgeranyl-protein + diphosphate
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + S-geranylgeranyl-Ki-Ras4B
diphosphate + S-geranylgeranyl-Ki-Ras4B
show the reaction diagram
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both the polylysine and the carboxy-terminal methionine are important for geranylgeranylation of this substrate
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Ala
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Ala
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Arg
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Arg
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Asn
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Asn
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Asp
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Asp
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Cys
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Cys
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Gln
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Gln
show the reaction diagram
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-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Ile
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Ile
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Leu
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Leu
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Met
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Met
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Phe
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Phe
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Ser
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Ser
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Thr
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Thr
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Tyr
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Tyr
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + Thr-Lys-Cys-Val-Ile-Val
diphosphate + Thr-Lys-(S-geranylgeranyl)-Cys-Val-Ile-Val
show the reaction diagram
-
-
-
-
?
Ser-Ser-Cys-Ile-Leu-Leu + geranylgeranyl diphosphate
diphosphate + Ser-Ser-S-geranylgeranyl-Cys-Ile-Leu-Leu
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
farnesyl diphosphate + protein-cysteine
S-farnesyl protein + diphosphate
show the reaction diagram
-
the enzyme catalyzes postttranslational modification of proteins, the farnesyl moieties attached to the substrates are direcly involved in protein-protein interactions as well as in protein-membrane interactions
-
-
?
geranylgeranyl diphosphate + protein-cysteine
S-geranylgeranyl protein + diphosphate
show the reaction diagram
-
the enzyme catalyzes posttranslational modification of proteins, the farnesyl moieties attached to the substrates are direcly involved in protein-protein interactions as well as in protein-membrane interactions
-
-
?
geranylgeranyl diphosphate + protein-cysteine
S-geranylgeranyl-protein + diphosphate
show the reaction diagram
geranylgeranyl diphosphate + Ras protein
S-geranylgeranyl-Ras protein + diphosphate
show the reaction diagram
geranylgeranyl diphosphate + Ras-CVLL
S-geranylgeranyl-Ras-CVLL + diphosphate
show the reaction diagram
-
tritium labelled geranylgeranyl diphosphate for enzyme assay, His-tagged geranylgeranyl diphosphate
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
-
60% of maximal activity in the presence of 0.5 mM alone
Zinc
-
all of the GGTase-I complexes contain a zinc ion bound at full occupancy with a B-factor comparable with the surrounding protein residues. The zinc ion is coordinated by three residues, Asp269b, Cys271b and His321b
additional information
-
metals not needed for complex formation between enzyme and geranylgeranyl diphosphate, but addition of prenyl acceptor only results in prenyl transfer in presence of Mg2+ and Zn2+; not: Co2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2R,3R,4S,5R)-2-(3,4-dichlorophenyl)-4-(hexylsulfanyl)-1-[(4-methylphenyl)sulfonyl]-5-propylpyrrolidine-3-carboxylic acid
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-
(2R,3R,4S,5R)-2-(4-bromophenyl)-1-[(4-methylphenyl)sulfonyl]-4-(pentylsulfanyl)-5-propylpyrrolidine-3-carboxylic acid
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-
(2R,3R,4S,5R)-2-(4-bromophenyl)-4-(hexylsulfanyl)-1-[(4-methylphenyl)sulfonyl]-5-propylpyrrolidine-3-carboxylic acid
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(2R,3R,4S,5R)-2-(4-bromophenyl)-4-[(4-methoxyphenyl)sulfanyl]-1-[(4-methylphenyl)sulfonyl]-5-propylpyrrolidine-3-carboxylic acid
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-
(2R,3R,4S,5R)-2-(4-bromophenyl)-5-ethyl-4-(hexylsulfanyl)-1-[(4-methylphenyl)sulfonyl]pyrrolidine-3-carboxylic acid
-
-
(2R,3R,4S,5R)-2-(4-bromophenyl)-5-hexyl-4-(hexylsulfanyl)-1-[(4-methylphenyl)sulfonyl]pyrrolidine-3-carboxylic acid
-
-
(2R,3R,4S,5R)-4-[(3-tert-butoxy-3-oxopropyl)sulfanyl]-2-(3-chlorophenyl)-5-(cyclopentylmethyl)-1-[(4-methylphenyl)sulfonyl]pyrrolidine-3-carboxylic acid
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-
(2R,3R,4S,5R)-4-[(3-tert-butoxy-3-oxopropyl)sulfanyl]-2-(4-chlorophenyl)-1-[(4-chlorophenyl)sulfonyl]-5-(cyclopentylmethyl)pyrrolidine-3-carboxylic acid
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-
(2R,3R,4S,5R)-4-[(3-tert-butoxy-3-oxopropyl)sulfanyl]-2-(4-chlorophenyl)-5-(cyclopentylmethyl)-1-(phenylsulfonyl)pyrrolidine-3-carboxylic acid
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-
(2S,5R)-5-ethyl-2-(4-fluorophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid
-
IC50: 0.2 mM using RhoA as a substrate, IC50: 0.25 mM using Ki-Ras4B as a substrate
(2S,5S)-5-tert-butyl-2-(4-chlorophenyl)-1-[(2-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole-3-carboxylic acid
(2S,6S)-2,6-bis(4-chlorophenyl)-1-[(2-methylphenyl)sulfonyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid
-
IC50: 0.0003 mM using RhoA as a substrate, IC50: 0.002 mM using Ki-Ras4B as a substrate
(2S,6S)-6-(4-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-2-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid
-
IC50: 0.12 mM using RhoA as a substrate, IC50: 0.08 mM using Ki-Ras4B as a substrate
(S)-N-(4-(3,4-dichlorophenoxy)benzyl)-6-(1H-indol-3-yl)piperazine-2,5-dione
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dual inhibitor for both farnesyl transferase and geranygeranyltransferase-I. Compound occupies both isoprenoid and peptide substrate binding sites
(S)-N-(4-(3-chlorophenoxy)benzyl)-6-(1H-indol-3-yl)piperazine-2,5-dione
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dual inhibitor for both farnesyl transferase and geranygeranyltransferase-I
1-phosphono-(E,E,E)-geranylgeraniol
1-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-cyclohexanecarboxylic acid
-
IC50: 6525 nM
1-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-cyclohexanecarboxylic acid methyl ester
-
IC50: above 0.01 mM
11-aminoundecylcarbonyl-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
-
competitive. bivalent inhibitor for simultaneous recognition of both exteriorand interior protein surface. Not inhibitory against farnesyltransferase
2-aryl-4-aminobenzoic acid
-
IC50: 21 nM
2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-N-(3-methyl-butyl)-acetamide
-
IC50: above 0.01 mM
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl] acetylamino}-4-methyl-pentanoic acid methyl ester
-
IC50: above 0.01 mM
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-3-phenyl-propionic acid
-
IC50: 0.0063 mM; IC50: 170 nM
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-3-phenyl-propionic acid methyl ester
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IC50: 4500 nM; IC50: above 0.01 mM
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methyl-pentanoic acid
-
IC50: 2700 nM; IC50: 580 nM
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methyl-pentanoic acid methyl ester
-
IC50: above 0.01 mM
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methylsulfanyl-butyric acid
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IC50: 3350 nM
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methylsulfanyl-butyric acid methyl ester
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IC50: above 0.01 mM
3-(4'-farnesyloxy-3'-methoxyphenyl)-2-trans propenoic acid
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0.1 mM, 83.9% inhibition
3-(4'-farnesyloxy-3'-OH-phenyl)-2-trans propenoic acid
-
0.1 mM, 93.5% inhibition
3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid
-
0.1 mM, 78.6% inhibition
3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid ethyl ester
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0.1 mM, 3% inhibition
3-(4'-geranyloxy-3'-OH-phenyl)-2-trans propenoic acid
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0.1 mM, 72.4% inhibition
3-(4'-geranyloxy-3'-OH-phenyl)-2-trans propenoic acid ethyl ester
-
0.1 mM, 7.5% inhibition
3-(4'-isopentenyloxy-3'-OH-phenyl)-2-trans propenoic acid
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0.1 mM, 46.4% inhibition
3-aza-geranylgeranyl-diphosphate
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competitive inhibitor with respect to geranylgeranyl diphosphate, non-competitive to Cys-Val-Phe-Leu
3-chloro-N-[2-oxo-2-[2-[[1-phenyl-3-(4-propoxyphenyl)pyrazol-4-yl]methylidene]hydrazinyl]ethyl]benzamide
-
GGTI-DU.Sig1, PubChem CID 3311883, inhibitor of protein geranylgeranyltransferase type I
4-[[([5-[(4-ethylphenoxy)methyl]-4-(1-phenylethyl)-4H-pyrazol-3-yl]sulfanyl)acetyl]amino]benzamide
-
inhibitor identified using quantitative structure-activity realtionship models and virtual screening of chemicals. confirmation of predicted data by experiment
4-[[2-[[5-(2-methoxyphenyl)-4-phenethyl-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzamide
-
GGTI-DU.En1, PubChem CID 2118978, inhibitor of protein geranylgeranyltransferase type I
4-[[2-[[5-[(4-ethylphenoxy)methyl]-4-(1-phenylethyl)-1,2,4-triazol-3-yl]sulfanyl]acetyl]amino]benzamide
-
GGTI-DU.En2, PubChem CID 3455185, inhibitor of protein geranylgeranyltransferase type I, no or little activity against protein farnesyltransferase
auraptene
-
0.1 mM, 18.6% inhibition
boropinic acid
-
0.1 mM, 31% inhibition
collinin
-
0.1 mM, 34.2% inhibition
Cys-3-(aminomethyl)benzoic acid-Leu
-
noncompetitive to geranylgeranyl diphosphate, competitive to dansyl-Gly-Cys-Ile-Ile-Leu
Cys-Val-Phe-Leu
-
noncompetitive inhibitor with respect to geranylgeranyl diphosphate, 50% inhibition at 0.0001 mM, competitive to Cys-Val-Phe-Leu
diethyl dicarbonate
-
80% loss of activity at 5 mM
GGTI-2151
16.3% inhibition at 50 nM
GGTI-2154
14.7% inhibition at 50 nM
GGTI-297
-
-
GGTI-298
GGTI-DU40
L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
-
-
N-(12-ammoniododecanoyl)-D-cysteinyl-L-valyl-L-isoleucyl-L-leucine trifluoroacetate
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N-(12-[[(3-[[(3R)-3-ammonio-4-phenylbutyl]oxy]-4,5-bis[[(3S)-3-ammonio-4-phenylbutyl]oxy]phenyl)carbonyl]amino]dodecanoyl)-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine tris(trifluoroacetate)
-
-
N-(2,5-dichlorophenyl)-N'-[[3-(4-methylphenyl)-1-phenylpyrazol-4-yl]methylideneamino]oxamide
-
GGTI-DU.Sig2, PubChem CID 4277701, inhibitor of protein geranylgeranyltransferase type I
N-(4-[[(3-[[(3R)-3-ammonio-4-phenylbutyl]oxy]-4,5-bis[[(3S)-3-ammonio-4-phenylbutyl]oxy]phenyl)carbonyl]amino]butanoyl)-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine tris(trifluoroacetate)
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N-benzyl-2-[(2-chlorobenzyl)[[5-(4-methylphenyl)-2H-tetrazol-2-yl]acetyl]amino]butanamide
-
inhibitor identified using quantitative structure-activity realtionship models and virtual screening of chemicals. confirmation of predicted data by experiment
N-benzyl-2-[(2-chlorophenyl)methyl-[2-[5-(4-methylphenyl)tetrazol-2-yl]acetyl]amino]butanamide
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GGTI-DU.As2, PubChem CID 3180738, inhibitor of protein geranylgeranyltransferase type I, no or little activity against protein farnesyltransferase
N-[(E)-1-(benzylcarbamoyl)-2-[5-(3,4-dichlorophenyl)furan-2-yl]ethenyl]-4-methylbenzamide
-
inhibitor identified using quantitative structure-activity realtionship models and virtual screening of chemicals. confirmation of predicted data by experiment
N-[12-([[3,4,5-tris(3-ammoniopropoxy)phenyl]carbonyl]amino)dodecanoyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine tris(trifluoroacetate)
-
-
N-[2-(benzylamino)-2-oxoethyl]-2-[5-(4-chlorophenyl)tetrazol-2-yl]-N-(4-propan-2-ylphenyl)acetamide
-
GGTI-DU.As1, PubChem CID 3180720, inhibitor of protein geranylgeranyltransferase type I
N-[3-(benzylamino)-1-[5-(3,4-dichlorophenyl)furan-2-yl]-3-oxoprop-1-en-2-yl]-4-methylbenzamide
-
GGTI-DU.Sig3, PubChem CID 5143450, inhibitor of protein geranylgeranyltransferase type I, no or little activity against protein farnesyltransferase
N-[6-(3,4,5-tris(3-amino-1-propoxy)benzoylamino)-undecylcarbonyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
-
competitive, bivalent inhibitor for simultaneous recognition of both exterior and interior protein surface. Not inhibitory against farnesyltransferase
N-[6-(3,4,5-tris(3-amino-4-phenyl-1-butoxy)benzoylamino)-hexylcarbonyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine trifluoroacetate
-
-
N-[6-(3,4,5-tris(3-amino-4-phenyl-1-butoxy)benzoylamino)-propylcarbonyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
-
bivalent inhibitor for simultaneous recognition of both exterior and interior protein surface. Not inhibitory against farnesyltransferase
N-[6-(3,4,5-tris(3-amino-4-phenyl-1-butoxy)benzoylamino)-undecylcarbonyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
-
competitive, bivalent inhibitor for simultaneous recognition of both exterior and interior protein surface. Not inhibitory against farnesyltransferase
NPFREKKFFCAIL
-
biotin-gamma6, substrate inhibition at high peptide concentration
PD-083176
-
noncompetitive to geranylgeranyl diphosphate, competitive to GST-CDC42, modest inhibitor
-
Phenylglyoxal
-
80% loss of activity, inactivation of inhibition in the presence of geranylgeranyl diphosphate
Thr-Lys-Cys-Val-Ile-Leu
-
potent competitor, 50% inhibition at 0.001 mM
Thr-Lys-Cys-Val-Ile-Met
-
potent competitor, 50% inhibition at 0.008 mM
umbelliprenine
-
0.1 mM, 13.4% inhibition
[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetic acid benzyl ester
-
IC50: above 0.01 mM
{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-acetic acid
-
IC50: above 0.01 mM
{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-acetic acid methyl ester
-
IC50: above 0.01 mM
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7-isopentenyloxycoumarin
-
0.1 mM, 10.3% activation
additional information
-
PGGT-I is specifically required for the jasmonic acid signalling triggering octadecanoid-derivative responsive Catharanthus AP2 domain 3 expression
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00027 - 0.025
(biotin-CONH-(CH2)5-CO-)-NPFREKKFFCAI-Leu
0.00003
3,7,11-trimethyl-12-(7-nitro-benzo[1,2,5]-oxadiazo-4-ylamino)-dodeca-2,6,10-trien-1-diphosphate
-
-
0.00002
Arg-Arg-Cys-Val-Leu-Leu
-
pH 7.6, 30C
0.00000133
Asp-Asp-Pro-Thr-Ala-Ser-Ala-Cys-Val-Leu-Leu
-
at 30C
0.0018 - 0.0024
dansyl-Gly-Cys-Ile-Ile-Leu
0.000003 - 0.001
geranylgeranyl diphosphate
0.00143
glutathione S-transferase-GCVKIKKCVIL
-
pH 7.5, 37C
-
0.016
GST-CDC42
-
pH 7.0, 30C, prenyl donor: geranylgeranyl diphosphate
-
0.042
GST-RhoA
-
-
-
0.0088
Ki-Ras4A
-
pH 7.5, 37C
-
0.012
Ki-Ras4B
-
pH 7.5, 37C
-
0.00013
Lys-Lys-Cys-Ile-Ile-Met
-
pH 7.6, 30C
0.002
Lys-Pro-Cys-Val-Val-Met
-
pH 7.6, 30C
0.0021
N-Ras
-
pH 7.5, 37C
-
0.002
Phe-Phe-Cys-Ala-Ile-Leu
-
pH 7.6, 30C
-
0.0009 - 0.0012
Ras-Cys-Val-Leu-Leu
0.0002
Ser-Ser-Cys-Ile-Leu-Leu
-
pH 7.4, 30C
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.028 - 0.12
(biotin-CONH-(CH2)5-CO-)-NPFREKKFFCAI-Leu
0.08
3,7,11-trimethyl-12-(7-nitro-benzo[1,2,5]-oxadiazo-4-ylamino)-dodeca-2,6,10-trien-1-diphosphate
Homo sapiens
-
-
0.021
Asp-Asp-Pro-Thr-Ala-Ser-Ala-Cys-Val-Leu-Leu
Homo sapiens
-
at 30C
0.02 - 0.34
geranylgeranyl diphosphate
0.0057
GST-CDC42
Bos taurus
-
prenyl donor: geranylgeranyl diphosphate
-
0.08
GST-RhoA
Homo sapiens
-
-
-
0.0667
Ki-Ras4A
Homo sapiens
-
-
-
0.0767
Ki-Ras4B
Homo sapiens
-
-
-
0.0113
N-Ras
Homo sapiens
-
-
-
0.014 - 0.02
Ras-Cys-Val-Leu-Leu
0.001
Thr-Lys-Cys-Val-Ile-Ala
0.0063
Thr-Lys-Cys-Val-Ile-Cys
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
0.001
Thr-Lys-Cys-Val-Ile-Gln
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
0.048
Thr-Lys-Cys-Val-Ile-Ile
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
0.088
Thr-Lys-Cys-Val-Ile-Leu
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
0.082
Thr-Lys-Cys-Val-Ile-Met
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
0.06
Thr-Lys-Cys-Val-Ile-Phe
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
0.001
Thr-Lys-Cys-Val-Ile-Ser
0.022
Thr-Lys-Cys-Val-Ile-Tyr
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
0.107
Thr-Lys-Cys-Val-Ile-Val
Escherichia coli
-
in 50 mM Tris-HCl, 5 mM dithiothreitol, 5 mM MgCl2, and 0.01 mM ZnCl2
additional information
additional information
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00086
1-P-GGOH
-
with respect to GST-CDC42
0.0002 - 0.00072
1-phosphono-(E,E,E)-geranylgeraniol
0.000015 - 0.000022
3-aza-geranylgeranyl-diphosphate
0.078 - 0.14
Cys-3-(aminomethyl)benzoicacid-Leu
0.00005 - 0.000065
Cys-Val-Phe-Leu
0.0082 - 0.0087
PD-083176
additional information
additional information
-
KI for varied concentrations of dansyl-Gly-Cys-Ile-Ile-Leu
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.25 - 4
(2S,5R)-5-ethyl-2-(4-fluorophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid
Homo sapiens
-
IC50: 0.2 mM using RhoA as a substrate, IC50: 0.25 mM using Ki-Ras4B as a substrate
0.0009 - 4
(2S,5S)-5-tert-butyl-2-(4-chlorophenyl)-1-[(2-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole-3-carboxylic acid
Homo sapiens
-
IC50: 0.0005 mM using RhoA as a substrate, IC50: 0.0009 mM using Ki-Ras4B as a substrate
0.002 - 4
(2S,6S)-2,6-bis(4-chlorophenyl)-1-[(2-methylphenyl)sulfonyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid
Homo sapiens
-
IC50: 0.0003 mM using RhoA as a substrate, IC50: 0.002 mM using Ki-Ras4B as a substrate
0.08 - 4
(2S,6S)-6-(4-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-2-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid
Homo sapiens
-
IC50: 0.12 mM using RhoA as a substrate, IC50: 0.08 mM using Ki-Ras4B as a substrate
0.021
(S)-N-(4-(3,4-dichlorophenoxy)benzyl)-6-(1H-indol-3-yl)piperazine-2,5-dione
Rattus norvegicus
-
pH 7.4, 30C
0.0323
(S)-N-(4-(3-chlorophenoxy)benzyl)-6-(1H-indol-3-yl)piperazine-2,5-dione
Rattus norvegicus
-
pH 7.4, 30C
0.006525
1-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-cyclohexanecarboxylic acid
Homo sapiens
-
IC50: 6525 nM
0.01
1-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-cyclohexanecarboxylic acid methyl ester
Homo sapiens
-
IC50: above 0.01 mM
0.0014
11-aminoundecylcarbonyl-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
Rattus norvegicus
-
-
0.000021
2-aryl-4-aminobenzoic acid
Homo sapiens
-
IC50: 21 nM
0.01
2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-N-(3-methyl-butyl)-acetamide
0.00017 - 0.0063
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-3-phenyl-propionic acid
0.0045 - 0.01
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-3-phenyl-propionic acid methyl ester
0.00058 - 0.0027
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methyl-pentanoic acid
0.01
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methyl-pentanoic acid methyl ester
Homo sapiens
-
IC50: above 0.01 mM
0.00335
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methylsulfanyl-butyric acid
Homo sapiens
-
IC50: 3350 nM
0.01
2-{2-[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetylamino}-4-methylsulfanyl-butyric acid methyl ester
Homo sapiens
-
IC50: above 0.01 mM
0.008
4-[[([5-[(4-ethylphenoxy)methyl]-4-(1-phenylethyl)-4H-pyrazol-3-yl]sulfanyl)acetyl]amino]benzamide
Rattus norvegicus
-
30C
0.00007
GGTI-DU40
Sus scrofa
-
complete inhibition at 5 microM, tritium-labelled geranylgeranyl diphosphate for activity assay with lysate of trabecular mesh cells, 30C
0.0048
L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
Homo sapiens
-
-
0.0014
N-(12-ammoniododecanoyl)-D-cysteinyl-L-valyl-L-isoleucyl-L-leucine trifluoroacetate
Homo sapiens
-
-
0.00098
N-(12-[[(3-[[(3R)-3-ammonio-4-phenylbutyl]oxy]-4,5-bis[[(3S)-3-ammonio-4-phenylbutyl]oxy]phenyl)carbonyl]amino]dodecanoyl)-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine tris(trifluoroacetate)
Homo sapiens
-
-
0.00066
N-(4-[[(3-[[(3R)-3-ammonio-4-phenylbutyl]oxy]-4,5-bis[[(3S)-3-ammonio-4-phenylbutyl]oxy]phenyl)carbonyl]amino]butanoyl)-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine tris(trifluoroacetate)
Homo sapiens
-
-
0.035
N-benzyl-2-[(2-chlorobenzyl)[[5-(4-methylphenyl)-2H-tetrazol-2-yl]acetyl]amino]butanamide
Rattus norvegicus
-
30C
0.043
N-[(E)-1-(benzylcarbamoyl)-2-[5-(3,4-dichlorophenyl)furan-2-yl]ethenyl]-4-methylbenzamide
Rattus norvegicus
-
30C
0.0006
N-[12-([[3,4,5-tris(3-ammoniopropoxy)phenyl]carbonyl]amino)dodecanoyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine tris(trifluoroacetate)
0.00066
N-[6-(3,4,5-tris(3-amino-4-phenyl-1-butoxy)benzoylamino)-propylcarbonyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
Rattus norvegicus
-
-
0.00064 - 0.00098
N-[6-(3,4,5-tris(3-amino-4-phenyl-1-butoxy)benzoylamino)-undecylcarbonyl]-L-cysteinyl-L-valyl-L-isoleucyl-L-leucine
0.01
[3-(1H-imidazol-4-ylmethyl)-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl]-acetic acid benzyl ester
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0059
-
-
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
enzyme is abundantly expressed in the developing rat cerebellum, in particular molecular layer, the region enriched with Purkinje cell dendrites
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
primary culture of airway smooth muscle cell
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37000
alpha-subunit
42000
beta subunit of PGGT-I, SDS-PAGE
82000
heterodimer of the alpha and beta subunits
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterodimer
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
side-chain modification
-
chemical modification with phenylglyoxal of arginine residue: 80% loss of activity in 30 min, chemical modification with diethyl dicarbonate of histidine residue: 80% loss of activity at 5 mM
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging-drop method, crystal structure of GGTase-I in complex with its cognate lipid substrate, geranylgeranylpyrophosphate
enzyme in complex with its substrate geranylgeranylpyrophosphate, hanging drop method, PCB buffer, pH 7.0 and 25% PEG 1500, cryoprotection in PCB vuffer, pH 7.0, 30% PEG 1500, and 10% ethylene glycol, flash frozen in liquid nitrogen, diffraction data collection at -173C
1. binary complex with geranylgeranyl diphosphate, 2. ternary complex with a non-hydrolyzable geranylgeranyl diphosphate analog and CaaX peptide, 3. binary complex with prenyl-peptide product and 4. ternary complex with prenylated product and geranylgeranyl diphosphate. GGTase-I crystals belong to the I222 space group, with three complete 91 kDa heterodimers in the asymmetric unit. GGTase-I crystals are grown at 17C in hanging drops using equal volumes of protein and reservoir solution (1.3 M (NH4)2SO4, 175 mM Na3 citrate pH 6.5, 20 mM dithiothreitol and 100 mM MES pH 6.3)
-
low-affinity ternary complex of L-778,123 bound in GGTase-I peptide-binding site and geranylgeranyl diphosphate bound in the lipid-binding site and complex of GGTase-I with L-778,123 and a sulfate anion
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.6
-
at pH 8.6 no enzyme activity is detected
636545
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
no enzyme activity in the presence of EDTA
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
centrifugation of cells, frozen paste resuspended in 20 mM Tris, pH 7.7 with 5 mM dithiothreitol, and 5 microM ZnCls, and protease inhibitor tablet, cells lysed with pressure homogenization, crude lysate clarified by centrifugation, applied to DEAE Sepharose column, fractionation with buffer and varying NaCl concentrations, pooling of fractions, addition of substrate geranylgeranylpyrophosphate to displace nonspecifically bound lipids, phenyl-Sepharose column fractionation with gradient of buffer with (NH4)2SO4, pooled fractions applied to Q-Sepharose column, fractionated with gradient of buffer and NaCl, concentration of active fractions, application to a 120-ml Superdex 16/10 gel filtration column, concentration of enzyme
nickel agarose resin chromatography
-
peptide affinity chromatography of enzyme on SSCILL-Sepharose
-
Q-Sepharose HP column chromatography and Superdex 200 gel filtration
recombinant enzyme
recombinant wild-type and mutant enzymes
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
alpha-subunit encoded by RAM2 and beta-subunit encoded by CDC43 translationally coupled by overlapping the RAM-CDC43 stop-start codons and by locating a ribosome-binding site near the 3' end of RAM2, recombinant enzyme overproduced in Escherichia coli
-
alpha-subunit encoded by RAM2 cloned to the pFC vector, which has an chloroamphenicol resistance gene and beta-subunit encoded by CAL1 cloned to the pFlag vector, which has an ampicillin resistance gene, these two recombinant enzymes are cotransformed and expressed in Escherichia coli
-
coexpression of two subunits of enzyme by Sf9 cells infected with recombinant baculovirus
-
expressed in Escherichia coli
-
expressed in Escherichia coli BL21 (DE3) and Sf9 insect cells
-
expressed in Escherichia coli strain BL21(DE3) GGPT/pET23a
-
expressed in Sf9 insect cells
identification of the cwp1+ gene, which encodes the alpha-subunit of enzyme, coexpression of cwp1p and cwg2p, beta-subunit, in Escherichia coli
-
PCR-amplification and expression in Escherichia coli
PCR-amplification of human enzyme for RT-PCR analysis of expression in human trabecular mesh cells
-
recombinant mammalian enzyme expressed in Sf9 cells
-
wild-type and mutant enzymes expressed in Escherichia coli
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Kbeta311A
-
mutation decreases prenylation rate constant in absence of Mg2+. Addition of Mg2+ increases geranylgeranylation rate constant
Kbeta311D
-
mutation decreases prenylation rate constant in absence of Mg2+. Addition of Mg2+ increases geranylgeranylation rate constant
D140N
-
alpha-subunit, increased Km
H145D
-
alpha-subunit, increased Km
H216D
-
beta-subunit, KM of geranylgeranyl diphosphate increased 12fold
N282A
-
alpha-subunit, increased Km
R166I
-
beta-subunit, KM of geranylgeranyl diphosphate increased 29fold, no forming of geranygeranyl diphosphate
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine