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Information on EC 2.5.1.153 - adenosine tuberculosinyltransferase
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2.5.1.153 adenosine tuberculosinyltransferaseIUBMB Comments
The enzyme, characterized from the bacterial pathogen Mycobacterium tuberculosis, produces 1-tuberculosinyladenosine, an unusual terpene nucleoside that acts as a phagolysosome disruptor by neutralizing the pH, resulting in swelling of the lysosome and obliteration of its multilamellar structure.
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Word Map
- 2.5.1.153
- tuberculosis
- mycobacterium
-
diterpene
-
avirulent
- bovis
- nucleoside
-
prenylation
-
isoprenoid
-
diterpenoids
- synthases
-
virulence-associated
-
geranylgeranyl
- cyclase
-
anti-infective
-
phagolysosome
- diagnostics
The expected taxonomic range for this enzyme is: Mycobacterium tuberculosis
Reaction Schemes
+
=
1-tuberculosinyladenosine
+
Synonyms
rv3378c, rv3378c protein, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EC 3.1.7.8
-
-
formerly
-
EC 3.1.7.9
-
-
formerly
-
Rv3378c
Rv3378c protein
Rv3378c
-
-
locus name
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
tuberculosinyl diphosphate + adenosine = 1-tuberculosinyladenosine + diphosphate
-
-
-
-
tuberculosinyl diphosphate + H2O = (13S)-isotuberculosinol + diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
tuberculosinyl diphosphate:adenosine tuberculosinyltransferase
The enzyme, characterized from the bacterial pathogen Mycobacterium tuberculosis, produces 1-tuberculosinyladenosine, an unusual terpene nucleoside that acts as a phagolysosome disruptor by neutralizing the pH, resulting in swelling of the lysosome and obliteration of its multilamellar structure.
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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
2 tuberculosinyl diphosphate + 2 H2O
(13R)-isotuberculosinol + (13S)-isotuberculosinol + 2 diphosphate
ent-copalyl diphosphate + H2O
(-)-ent copalol + ent-13-epi-manool + ent-manool + diphosphate
syn-copalyl diphosphate + H2O
syn-copalol + (13R)-vitexifolin + (13S)-vitexifolin + diphosphate
2 tuberculosinyl diphosphate + 2 H2O
(13R)-isotuberculosinol + (13S)-isotuberculosinol + 2 diphosphate
-
-
isotuberculosinol is also named nosyberkol, the product ratio of (13R)-isotuberculosinol and (13S)-isotuberculosinol is 1:3
-
?
2 tuberculosinyl diphosphate + 2 H2O
(13R)-isotuberculosinol + (13S)-isotuberculosinol + 2 diphosphate
-
-
the product ratio of (13R)-isotuberculosinol and (13S)-isotuberculosinol is 1:3
-
?
2 tuberculosinyl diphosphate + 2 H2O
(13R)-isotuberculosinol + (13S)-isotuberculosinol + 2 diphosphate
-
-
isotuberculosinol is also named nosyberkol, the product ratio of (13R)-isotuberculosinol and (13S)-isotuberculosinol is 1:3
-
?
2 tuberculosinyl diphosphate + 2 H2O
(13R)-isotuberculosinol + (13S)-isotuberculosinol + 2 diphosphate
-
-
the product ratio of (13R)-isotuberculosinol and (13S)-isotuberculosinol is 1:3
-
?
copalyl diphosphate + H2O
(+)-copalol + manool + 13-epi-manool + diphosphate
-
-
40% (+)-copalol, 12% manool and 15% 13-epi-manool
-
?
copalyl diphosphate + H2O
(+)-copalol + manool + 13-epi-manool + diphosphate
-
-
40% (+)-copalol, 12% manool and 15% 13-epi-manool
-
?
ent-copalyl diphosphate + H2O
(-)-ent copalol + ent-13-epi-manool + ent-manool + diphosphate
-
-
22% (-)-ent copalol, 8% ent-13-epi-mancol, and 42% ent-manool
-
?
ent-copalyl diphosphate + H2O
(-)-ent copalol + ent-13-epi-manool + ent-manool + diphosphate
-
-
22% (-)-ent copalol, 8% ent-13-epi-mancol, and 42% ent-manool
-
?
syn-copalyl diphosphate + H2O
syn-copalol + (13R)-vitexifolin + (13S)-vitexifolin + diphosphate
-
-
16% syn-copalol, 3% (13R)-vitrxifolin and 59% (13S)-vitexifolin
-
?
syn-copalyl diphosphate + H2O
syn-copalol + (13R)-vitexifolin + (13S)-vitexifolin + diphosphate
-
-
16% syn-copalol, 3% (13R)-vitrxifolin and 59% (13S)-vitexifolin
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
-
-
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
-
-
-
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
the enzyme produces 1-tuberculosinyladenosine, an abundant amphiphile that is exported outside Mycobacterium tuberculosis
-
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
-
-
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
the enzyme produces 1-tuberculosinyladenosine, an abundant amphiphile that is exported outside Mycobacterium tuberculosis
-
-
?
tuberculosinyl diphosphate + H2O
(13S)-isotuberculosinol + diphosphate
-
wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol, reaction of EC 3.1.7.9. Wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol
-
?
tuberculosinyl diphosphate + H2O
(13S)-isotuberculosinol + diphosphate
-
-
reaction of EC 3.1.7.9. Wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol
-
?
tuberculosinyl diphosphate + H2O
(13S)-isotuberculosinol + diphosphate
-
wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol, reaction of EC 3.1.7.9. Wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol
-
?
tuberculosinyl diphosphate + H2O
tuberculosinol + diphosphate
-
-
-
-
?
tuberculosinyl diphosphate + H2O
tuberculosinol + diphosphate
-
reaction of EC 3.1.7.8. Wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol
-
?
tuberculosinyl diphosphate + H2O
tuberculosinol + diphosphate
wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol
-
-
?
tuberculosinyl diphosphate + H2O
tuberculosinol + diphosphate
-
reaction of EC 3.1.7.8. Wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol
-
?
tuberculosinyl diphosphate + H2O
tuberculosinol + diphosphate
wild-type synthesizes 41% (13S)-isotuberculosinol and 59% tuberculosinol
-
-
?
tuberculosinyl diphosphate + H2O
tuberculosinol + diphosphate
-
-
-
-
?
additional information
?
-
-
no activity with geranyl diphosphate, farnesyl diphosphate or geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
no activity with terpentedienyl diphosphate, geranylgeranyl diphosphate, farnesyl diphosphate, and geranyl diphosphate
-
-
?
additional information
?
-
-
no activity with geranyl diphosphate, farnesyl diphosphate or geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
no activity with terpentedienyl diphosphate, geranylgeranyl diphosphate, farnesyl diphosphate, and geranyl diphosphate
-
-
?
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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
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
-
-
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
the enzyme produces 1-tuberculosinyladenosine, an abundant amphiphile that is exported outside Mycobacterium tuberculosis
-
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
-
-
-
?
tuberculosinyl diphosphate + adenosine
1-tuberculosinyladenosine + diphosphate
the enzyme produces 1-tuberculosinyladenosine, an abundant amphiphile that is exported outside Mycobacterium tuberculosis
-
-
?
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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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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Tuberculosis
Characterization of the Rv3378c gene product, a new diterpene synthase for producing tuberculosinol and (13R, S)-isotuberculosinol (nosyberkol), from the Mycobacterium tuberculosis H37Rv genome.
Tuberculosis
Identification of a New Diterpene Biosynthetic Gene Cluster that Produces O-Methylkolavelool in Herpetosiphon aurantiacus.
Tuberculosis
Molecular profiling of Mycobacterium tuberculosis identifies tuberculosinyl nucleoside products of the virulence-associated enzyme Rv3378c.
Tuberculosis
Structure and inhibition of tuberculosinol synthase and decaprenyl diphosphate synthase from Mycobacterium tuberculosis.
Tuberculosis
Substrate specificity of Rv3378c, an enzyme from Mycobacterium tuberculosis, and the inhibitory activity of the bicyclic diterpenoids against macrophage phagocytosis.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0254
tuberculosinyl diphosphate
-
mutant enzyme D82N, at pH 7.0, 45°C
0.0271
tuberculosinyl diphosphate
-
wild type enzyme, at pH 7.0, 45°C
0.0273
tuberculosinyl diphosphate
-
mutant enzyme D85N, at pH 7.0, 45°C
0.0396
tuberculosinyl diphosphate
-
mutant enzyme D81N, at pH 7.0, 45°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000998
tuberculosinyl diphosphate
-
mutant enzyme D82N, at pH 7.0, 45°C
0.00018
tuberculosinyl diphosphate
-
mutant enzyme D81N, at pH 7.0, 45°C
0.000192
tuberculosinyl diphosphate
-
mutant enzyme D85N, at pH 7.0, 45°C
0.000517
tuberculosinyl diphosphate
-
wild type enzyme, at pH 7.0, 45°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00398
tuberculosinyl diphosphate
-
mutant enzyme D82N, at pH 7.0, 45°C
0.0045
tuberculosinyl diphosphate
-
mutant enzyme D81N, at pH 7.0, 45°C
0.007
tuberculosinyl diphosphate
-
mutant enzyme D85N, at pH 7.0, 45°C
0.0191
tuberculosinyl diphosphate
-
wild type enzyme, at pH 7.0, 45°C
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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
bifunctional tuberculosinol/iso-tuberculosinol synthase, ECs 3.1.7.8 and 3.1.7.9
UniProt
brenda
bifunctional tuberculosinol/iso-tuberculosinol synthase, ECs 3.1.7.8 and 3.1.7.9
UniProt
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
physiological function
evolution
adenosine tuberculosinyltransferase is known only in Mycobacterium tuberculosis. This intersection of nucleoside andterpene pathways likely arose late in the evolution of the Mycobacterium tuberculosis complex
evolution
-
adenosine tuberculosinyltransferase is known only in Mycobacterium tuberculosis. This intersection of nucleoside andterpene pathways likely arose late in the evolution of the Mycobacterium tuberculosis complex
-
physiological function
the extracellular export of the amphipathic molecule 1-tuberculosinyladenosine likely accounts for the known virulence-promoting effects of the Rv3378c enzyme
physiological function
-
the extracellular export of the amphipathic molecule 1-tuberculosinyladenosine likely accounts for the known virulence-promoting effects of the Rv3378c enzyme
-
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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). TUBAT_MYCTO
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
296
0
34031
Swiss-Prot
-
TUBAT_MYCTU
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
296
0
34031
Swiss-Prot
-
TUBAT_MYCTU
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
296
0
34031
Swiss-Prot
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
homodimer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
native enzyme and complexes with inhibitor BPH-629, and mutants Y51F with TPP, mutant Y51F/Y90F with TPP, to 1.8-2.7 A resolution
vapor diffusion, and 2.2 A resolution, crystal structure reveals a cis-prenyl transferase fold with hydrophobic residues for isoprenoid binding and a second binding pocket suitable for the nucleoside substrate
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D34A
compared to wild-type, mutant produces about 1% (13S)-isotuberculosinol and 60% tuberculosinol
R38A
compared to wild-type, mutant produces about 5% (13S)-isotuberculosinol and 140% tuberculosinol
Y51F
production of both (13S)-isotuberculosinol and tuberculosinol is reduced
Y90F
compared to wild-type, mutant produces about 1% (13S)-isotuberculosinol and 49% tuberculosinol
D34A
-
compared to wild-type, mutant produces about 1% (13S)-isotuberculosinol and 60% tuberculosinol
-
R38A
-
compared to wild-type, mutant produces about 5% (13S)-isotuberculosinol and 140% tuberculosinol
-
Y51F
-
production of both (13S)-isotuberculosinol and tuberculosinol is reduced
-
Y90F
-
compared to wild-type, mutant produces about 1% (13S)-isotuberculosinol and 49% tuberculosinol
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA column chromatography, amylase column chromatography, and G3000SWXL gel filtration
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
diagnostics
diagnostics
the Mycobacterium tuberculosis-specific lipid 1-tuberculosinyladenosine is a target for diagnosing tuberculosis disease
diagnostics
-
the Mycobacterium tuberculosis-specific lipid 1-tuberculosinyladenosine is a target for diagnosing tuberculosis disease
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Nakano, C.; Ootsuka, T.; Takayama, K.; Mitsui, T.; Sato, T.; Hoshino, T.
Characterization of the Rv3378c gene product, a new diterpene synthase for producing tuberculosinol and (13R,S)-isotuberculosinol (nosyberkol), from the Mycobacterium tuberculosis H37Rv genome
Biosci. Biotechnol. Biochem.
75
75-81
2011
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
Hoshino, T.; Nakano, C.; Ootsuka, T.; Shinohara, Y.; Hara, T.
Substrate specificity of Rv3378c, an enzyme from Mycobacterium tuberculosis, and the inhibitory activity of the bicyclic diterpenoids against macrophage phagocytosis
Org. Biomol. Chem.
9
2156-2165
2011
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
Chan, H.C.; Feng, X.; Ko, T.P.; Huang, C.H.; Hu, Y.; Zheng, Y.; Bogue, S.; Nakano, C.; Hoshino, T.; Zhang, L.; Lv, P.; Liu, W.; Crick, D.C.; Liang, P.H.; Wang, A.H.; Oldfield, E.; Guo, R.T.
Structure and inhibition of tuberculosinol synthase and decaprenyl diphosphate synthase from Mycobacterium tuberculosis
J. Am. Chem. Soc.
136
2892-2896
2014
Mycobacterium tuberculosis (P9WJ61), Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618 (P9WJ61)
brenda
Young, D.; Layre, E.; Pan, S.; Tapley, A.; Adamson, J.; Seshadri, C.; Wu, Z.; Buter, J.; Minnaard, A.; Coscolla, M.; Gagneux, S.; Copin, R.; Ernst, J.; Bishai, W.; Snider, B.; Moody, D.
In vivo biosynthesis of terpene nucleosides provides unique chemical markers of mycobacterium tuberculosis infection
Chem. Biol.
22
516-526
2015
Mycobacterium tuberculosis (P9WJ61), Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618 (P9WJ61)
brenda
Ghanem, M.; Dub, J.; Wang, J.; McIntosh, F.; Houle, D.; Domenech, P.; Reed, M.; Raman, S.; Buter, J.; Minnaard, A.; Branch Moody, D.; Behra, M.
Heterologous production of 1-tuberculosinyladenosine in Mycobacterium kansasii models pathoevolution towards the transcellular lifestyle of mycobacterium tuberculosis
mBio
11
1-15
2020
Mycobacterium tuberculosis (P9WJ61), Mycobacterium tuberculosis ATCC 25618 (P9WJ61)
brenda
Layre, E.; Lee, H.J.; Young, D.C.; Martinot, A.J.; Buter, J.; Minnaard, A.J.; Annand, J.W.; Fortune, S.M.; Snider, B.B.; Matsunaga, I.; Rubin, E.J.; Alber, T.; Moody, D.B.
Molecular profiling of Mycobacterium tuberculosis identifies tuberculosinyl nucleoside products of the virulence-associated enzyme Rv3378c
Proc. Natl. Acad. Sci. USA
111
2978-2983
2014
Mycobacterium tuberculosis (P9WJ61), Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618 (P9WJ61)
brenda
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