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Information on EC 2.5.1.41 - phosphoglycerol geranylgeranyltransferase
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2.5.1.41 phosphoglycerol geranylgeranyltransferaseIUBMB Comments
This cytosolic enzyme catalyses the first pathway-specific step in the biosynthesis of the core membrane diether lipids in archaebacteria . Requires Mg2+ for maximal activity . It catalyses the alkylation of the primary hydroxy group in sn-glycerol 1-phosphate by geranylgeranyl diphosphate (GGPP) in a prenyltransfer reaction where a hydroxy group is the nucleophile in the acceptor substrate . The other enzymes involved in the biosynthesis of polar lipids in Archaea are EC 1.1.1.261 (sn-glycerol-1-phosphate dehydrogenase), EC 2.5.1.42 (geranylgeranylglycerol-phosphate geranylgeranyltransferase) and EC 2.7.7.67 (CDP-archaeol synthase), which lead to the formation of CDP-unsaturated archaeol. The final step in the pathway involves the addition of L-serine, with concomitant removal of CMP, leading to the production of unsaturated archaetidylserine .
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Word Map
- 2.5.1.41
-
geranylgeranylation
-
farnesylation
-
prenylation
-
isoprenoids
- prenyltransferases
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isoprenylation
- ggtase
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farnesyl-transferase
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escort
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hexamerization
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tetraether
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thermoplasma
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tim-barrel
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Reaction Schemes
Synonyms
((S)-GGGP) synthase, (S)-3-O-geranylgeranylglyceryl phosphate synthase, (S)-3-O-geranylgeranylglycerylphosphate, geranylgeranyl diphosphate:sn-3-O-(geranylgeranyl)glycerol 1-phosphate geranylgeranyltransferase, geranylgeranyl-transferase, geranylgeranylglycerol-phosphate geranylgeranyltransferase, geranylgeranylglyceryl phosphate synthase, geranylgeranyltransferase II, geranylgeranyltransferase, geranylgeranyloxyglycerol phosphate, GGGP synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(S)-3-O-geranylgeranylglyceryl phosphate synthase
geranylgeranyl diphosphate:sn-3-O-(geranylgeranyl)glycerol 1-phosphate geranylgeranyltransferase
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-
-
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geranylgeranyl-transferase
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-
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geranylgeranylglycerol-phosphate geranylgeranyltransferase
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geranylgeranylglyceryl phosphate synthase
geranylgeranyltransferase II
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-
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geranylgeranyltransferase, geranylgeranyloxyglycerol phosphate
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GGGP synthase
GGGPS
glycerol phosphate feranylgeranyltransferase
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prenyltransferase
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geranylgeranylglyceryl phosphate synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranylgeranyl diphosphate + sn-glycerol 1-phosphate = diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
alkenyl group transfer
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-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
geranylgeranyl diphosphate:sn-glyceryl phosphate geranylgeranyltransferase
This cytosolic enzyme catalyses the first pathway-specific step in the biosynthesis of the core membrane diether lipids in archaebacteria [2]. Requires Mg2+ for maximal activity [2]. It catalyses the alkylation of the primary hydroxy group in sn-glycerol 1-phosphate by geranylgeranyl diphosphate (GGPP) in a prenyltransfer reaction where a hydroxy group is the nucleophile in the acceptor substrate [2]. The other enzymes involved in the biosynthesis of polar lipids in Archaea are EC 1.1.1.261 (sn-glycerol-1-phosphate dehydrogenase), EC 2.5.1.42 (geranylgeranylglycerol-phosphate geranylgeranyltransferase) and EC 2.7.7.67 (CDP-archaeol synthase), which lead to the formation of CDP-unsaturated archaeol. The final step in the pathway involves the addition of L-serine, with concomitant removal of CMP, leading to the production of unsaturated archaetidylserine [5].
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CAS REGISTRY NUMBER
COMMENTARY
124650-69-7
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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
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-O-(geranylgeranyl)glyceryl 1-phosphate
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-
-
-
?
geranylgeranyl diphosphate + sn-glyceryl phosphate
diphosphate + sn-3-O-(geranylgeranyl)glyceryl 1-phosphate
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
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-
-
-
?
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
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-
-
?
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
first committed step in the biosynthetic pathway of glycerol dibiphytanyl glycerol tetraethers, the membrane lipids of the thermophilic and acidophilic euryarchaeota
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-
?
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
-
-
-
?
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
first committed step in the biosynthetic pathway of glycerol dibiphytanyl glycerol tetraethers, the membrane lipids of the thermophilic and acidophilic euryarchaeota
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-
?
geranylgeranyl diphosphate + sn-glyceryl phosphate
diphosphate + sn-3-O-(geranylgeranyl)glyceryl 1-phosphate
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-
-
-
?
geranylgeranyl diphosphate + sn-glyceryl phosphate
diphosphate + sn-3-O-(geranylgeranyl)glyceryl 1-phosphate
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-
-
-
?
geranylgeranyl diphosphate + sn-glyceryl phosphate
diphosphate + sn-3-O-(geranylgeranyl)glyceryl 1-phosphate
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-
-
-
?
additional information
?
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probably involved in the biosynthesis of membrane lipids in archaebacteriae
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-
?
additional information
?
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probably involved in the biosynthesis of membrane lipids in archaebacteriae
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-
?
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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
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
-
-
-
-
?
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
first committed step in the biosynthetic pathway of glycerol dibiphytanyl glycerol tetraethers, the membrane lipids of the thermophilic and acidophilic euryarchaeota
-
-
?
geranylgeranyl diphosphate + sn-glycerol 1-phosphate
diphosphate + 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate
first committed step in the biosynthetic pathway of glycerol dibiphytanyl glycerol tetraethers, the membrane lipids of the thermophilic and acidophilic euryarchaeota
-
-
?
additional information
?
-
-
probably involved in the biosynthesis of membrane lipids in archaebacteriae
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-
?
additional information
?
-
-
probably involved in the biosynthesis of membrane lipids in archaebacteriae
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-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Triton X-100
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required for enzymatic activity, optimal concentration: 0.01%
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Graft vs Host Disease
Inhibition of protein geranylgeranylation and farnesylation protects against GvHD via effects on CD4 effector T cells.
Leukemia
Inhibition of protein geranylgeranylation and farnesylation protects against GvHD via effects on CD4 effector T cells.
Neoplasms
Farnesyltransferase and geranylgeranyltransferase I inhibitors and cancer therapy: lessons from mechanism and bench-to-bedside translational studies.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0041
geranylgeranyl diphosphate
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Vmax: 0.004 mmol/min/mg
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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from an early stationary phase culture
brenda
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from an early stationary phase culture
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brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
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diversity of thaumarchaeotal GGGP synthases in the marine water column, phylogenetic analysis and tree and correlation to the classification of shallow and deep water clusters, overview. Differences in isoprenoid glycerol dialkyl glycerol tetraethers distributions from subsurface to deep waters that may be explained by differences in the GGGP synthase, suggesting a genetic control on isoprenoid glycerol dialkyl glycerol tetraethers distribution. Diversity of archaeal GGGP synthases, overview
metabolism
physiological function
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the key enzyme catalyses the formation of an ether bond between isoprenyl diphosphate and glycerol-1-phosphate to form 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate, and is the first committed step towards ether membrane lipid synthesis
metabolism
first committed step in the biosynthetic pathway of glycerol dibiphytanyl glycerol tetraethers, the membrane lipids of the thermophilic and acidophilic euryarchaeota
metabolism
-
first committed step in the biosynthetic pathway of glycerol dibiphytanyl glycerol tetraethers, the membrane lipids of the thermophilic and acidophilic euryarchaeota
-
Show AA Sequence and Transmembrane Helices (3939 entries)
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Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
hexamer
hexamer
the oligomerization interfaces are studied by introducing disturbing mutations and subsequently the stability and activity of generated dimeric and monomeric variants are compared with the wild-type enzyme. Oligomerization might positively affect the thermostability-flexibility trade-off in the enzyme by allowing a higher intrinsic flexibility of the individual protomers
hexamer
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the oligomerization interfaces are studied by introducing disturbing mutations and subsequently the stability and activity of generated dimeric and monomeric variants are compared with the wild-type enzyme. Oligomerization might positively affect the thermostability-flexibility trade-off in the enzyme by allowing a higher intrinsic flexibility of the individual protomers
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging drop vapour diffusion method using 100 mM citrate, pH 6.0, 10 mM MgCl2, 4-10% polyethylene glycol 4000
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sitting-drop vapor-diffusion method at 20°C, crystal structure of the enzyme in complex with substrate sn-glycerol-1-phosphate is determined at 2.35 A resolution
hanging-drop vapor diffusion method. 1.72 A resolution crystal structure of the enzyme in complex with glycerol and sulfate
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
using ammonium sulfate precipitation, four chromatographic steps (DE52, Q-Sepharose, phenyl-Superose, and Protein Pak)
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using DEAE-cellulose column chromatography, NH4SO4 precipitation, Phenyl-650S and Resourse Q columns, Mini Q column and Superdex 200 HR 10/30 column
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
diversity of thaumarchaeotal GGGP synthases in the marine water column, phylogenetic analysis and tree and correlation to the classification of shallow and deep water clusters, overview
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Zhang, D.L.; Daniels, L.; Poulter, C.D.
Biosynthesis of archaebacterial membranes. Formation of isoprene ethers by a prenyl transfer reaction
J. Am. Chem. Soc.
112
1264-1265
1990
Methanothermobacter thermautotrophicus, Methanothermobacter thermautotrophicus Marburg / DSM 2133
-
brenda
Payandeh, J.; Fujihashi, M.; Gillon, W.; Pai, E.F.
The crystal structure of (S)-3-O-geranylgeranylglyceryl phosphate synthase reveals an ancient fold for an ancient enzyme
J. Biol. Chem.
281
6070-6078
2006
Archaeoglobus fulgidus
brenda
Nemoto, N.; Oshima, T.; Yamagishi, A.
Purification and characterization of geranylgeranylglyceryl phosphate synthase from a thermoacidophilic archaeon, Thermoplasma acidophilum
J. Biochem.
133
651-657
2003
Thermoplasma acidophilum
brenda
Chen, A.; Zhang, D.; Poulter, C.
(S)-geranylgeranylglyceryl phosphate synthase. Purification and characterization of the first pathway-specific enzyme in archaebacterial membrane lipid biosynthesis
J. Biol. Chem.
268
21701-21705
1993
Methanothermobacter thermautotrophicus
brenda
Villanueva, L.; Schouten, S.; Sinninghe Damste, J.S.
Depth-related distribution of a key gene of the tetraether lipid biosynthetic pathway in marine Thaumarchaeota
Environ. Microbiol.
17
3527-3539
2015
Thaumarchaeota
brenda
Blank, P.N.; Barnett, A.A.; Ronnebaum, T.A.; Alderfer, K.E.; Gillott, B.N.; Christianson, D.W.; Himmelberger, J.A.
Structural studies of geranylgeranylglyceryl phosphate synthase, a prenyltransferase found in thermophilic Euryarchaeota
Acta Crystallogr. Sect. D
76
542-557
2020
Thermoplasma volcanium (Q97AR4), Thermoplasma volcanium, Thermoplasma volcanium ATCC 51530 (Q97AR4)
brenda
Nemoto, N.; Miyazono, K.I.; Tanokura, M.; Yamagishi, A.
Crystal structure of (S)-3-O-geranylgeranylglyceryl phosphate synthase from Thermoplasma acidophilum in complex with the substrate sn-glycerol 1-phosphate
Acta Crystallogr. Sect. F
75
470-479
2019
Thermoplasma acidophilum (Q9HJH3), Thermoplasma acidophilum, Thermoplasma acidophilum ATCC 25905 (Q9HJH3)
brenda
Linde, M.; Heyn, K.; Merkl, R.; Sterner, R.; Babinger, P.
Hexamerization of geranylgeranylglyceryl phosphate synthase ensures structural integrity and catalytic activity at high temperatures
Biochemistry
57
2335-2348
2018
Methanothermobacter thermautotrophicus (O26652), Methanothermobacter thermautotrophicus, Methanothermobacter thermautotrophicus ATCC 29096 (O26652)
brenda
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