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Information on EC 2.1.1.255 - geranyl diphosphate 2-C-methyltransferase and Organism(s) Streptomyces lasalocidi and UniProt Accession D3KYU3
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2.1.1.255 geranyl diphosphate 2-C-methyltransferaseIUBMB Comments
This enzyme, along with EC 4.2.3.118, 2-methylisoborneol synthase, produces 2-methylisoborneol, an odiferous compound produced by soil microorganisms with a strong earthy/musty odour.
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Word Map
- 2.1.1.255
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cyclization
- 2-methylisoborneol
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terpenoids
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c-methylation
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taste
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monoterpene
- coelicolor
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carbocation
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odor
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actinomycete
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isoprenoids
- cyanobacteria
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terpene
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sam-dependent
- limnetica
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s-adenosyl-l-methionine-dependent
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unpleasant
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dimethylallyl
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farnesyl
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pseudanabaena
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t-butyl
- ethylbenzene
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intermediacy
- lanosterol
The taxonomic range for the selected organisms is: Streptomyces lasalocidi
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
Synonyms
gppmt, c-methyl transferase, sco7701, gpp methyltransferase, sco7701 protein, geranyl pyrophosphate methyltransferase, geranyl diphosphate c-methyltransferase, geranyl diphosphate 2-methyltransferase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-methyl-GPP synthase
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geranyl pyrophosphate methyltransferase
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-
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GPP methyltransferase
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GPPMT
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MGPPS
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SCO7701
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + geranyl diphosphate = S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
biosynthetic mechanism, overview
PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:geranyl-diphosphate 2-C-methyltransferase
This enzyme, along with EC 4.2.3.118, 2-methylisoborneol synthase, produces 2-methylisoborneol, an odiferous compound produced by soil microorganisms with a strong earthy/musty odour.
CAS REGISTRY NUMBER
COMMENTARY
57219-74-6
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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
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
methylation of geranyl diphosphate before the cyclization reaction
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-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
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GC-MS analysis of products
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
the enzyme is involved in the biosynthesis of the terpenoid alcohol 2-methylisoborneol
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-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
-
methylation of geranyl diphosphate before the cyclization reaction
-
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
-
-
GC-MS analysis of products
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
-
the enzyme is involved in the biosynthesis of the terpenoid alcohol 2-methylisoborneol
-
-
?
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
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
methylation of geranyl diphosphate before the cyclization reaction
-
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
-
-
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
the enzyme is involved in the biosynthesis of the terpenoid alcohol 2-methylisoborneol
-
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
-
methylation of geranyl diphosphate before the cyclization reaction
-
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
-
-
-
-
?
S-adenosyl-L-methionine + geranyl diphosphate
S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate
-
the enzyme is involved in the biosynthesis of the terpenoid alcohol 2-methylisoborneol
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
the enzyme is important in the biosynthesis of 2-methylisoborneol, which involves the methylation of geranyl diphosphate by GPP methyltransferase and its subsequent cyclization by monoterpene cyclase to 2-methylisoborneol
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). CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified recombinant His6-tagged apo-GPPMT containing one molecule in the asymmetric unit, or in ternary complex with geranyl diphosphate and sinefungin, hanging drop method, mixing of protein solution containing 5 mg/ml in 50 mM sodium phosphate, pH 7.5, 300 mM NaCl and 10% glycerol, with S-adenosyl-L-methionine at a protein:S-adenosyl-L-methionine molar ratio of 1:7, 4°C, and further with reservoir solution containing 50 mM sodium cacodylate, pH 6.5, 1.4 M lithium sulfate, 30 mM MgCl2, and 1 mM spermine for GPPMT-GPP-SFG form I, or 50 mM sodium cacodylate, pH 6.7, 1.3 M lithium sulfate, 30 mM MgCl2, and 1 mM spermine for GPPMT-GPP-SFG form II, method screening, X-ray diffraction structure determination and analysis at 1.7-3.5 A resolution, molecular replacement method
purified recombinant His6-tagged apo-GPPMT containing one molecule in the asymmetric unit, or in ternary complex with geranyl diphosphate and sinefungin, hanging drop method, mixing of protein solution containing 5 mg/ml in 50 mM sodium phosphate, pH 7.5, 300 mM NaCl and 10% glycerol, with S-adenosyl-L-methionine at a protein:S-adenosyl-L-methionine molar ratio of 1:7, 4°C, and further with reservoir solution containing 50 mM sodium cacodylate, pH 6.5, 1.4 M lithium sulfate, 30 mM MgCl2, and 1 mM spermine for GPPMT-GPP-SFG form I, or 50 mM sodium cacodylate, pH 6.7, 1.3 M lithium sulfate, 30 mM MgCl2, and 1 mM spermine for GPPMT-GPP-SFG form II, method screening, X-ray diffraction structure determination and analysis at 1.7-3.5 A resolution, molecular replacement method
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli strain BL21 (DE3) by nickel affinity chromatography and gel filtration
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, genetic organization, phylogenetic analysis and tree, expression in Escherichia coli
expression of His6-tagged enzyme in Escherichia coli strain BL21 (DE3)
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ariyawutthiphan, O.; Ose, T.; Tsuda, M.; Gao, Y.; Yao, M.; Minami, A.; Oikawa, H.; Tanaka, I.
Crystallization and preliminary X-ray crystallographic study of a methyltransferase involved in 2-methylisoborneol biosynthesis in Streptomyces lasaliensis
Acta Crystallogr. Sect. F
67
417-420
2011
Streptomyces lasalocidi (D3KYU3), Streptomyces lasalocidi
Komatsu, M.; Tsuda, M.; Omura, S.; Oikawa. H.; Ikeda, H.
Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol
Proc. Natl. Acad. Sci. USA
105
7422-7427
2008
Micromonospora olivasterospora (F5HSX5), Micromonospora olivasterospora, Micromonospora olivasterospora KY11048 (F5HSX5), Micromonospora olivasterospora KY11048, Saccharopolyspora erythraea (A4FG18), Saccharopolyspora erythraea, Saccharopolyspora erythraea NRRL 2338 (A4FG18), Saccharopolyspora erythraea NRRL 2338, Streptomyces ambofaciens (A3KI18), Streptomyces ambofaciens ISP5053 (A3KI18), Streptomyces lasalocidi (D3KYU3), Streptomyces lasalocidi, Streptomyces lasalocidi NRRL2382R (D3KYU3)
EXTERNAL LINKS (specific for EC-Number 2.1.1.255)
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Release 2023.1 (January 2023)
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