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Enzyme Nomenclature
Information on EC 2.5.1.136 - 2-acylphloroglucinol 4-prenyltransferase
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EC Tree
2.5.1.136 2-acylphloroglucinol 4-prenyltransferaseIUBMB Comments
The enzyme, characterized from hop (Humulus lupulus), acts on phlorisovalerophenone, phlormethylbutanophenone, and phlorisobutanophenone during the synthesis of bitter acids. It also acts with much lower activity on naringenin chalcone. Forms a complex with EC 2.5.1.137, 2-acyl-4-prenylphloroglucinol 6-prenyltransferase, which catalyses additional prenylation reactions. Requires Mg2+.
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Word Map
- 2.5.1.136
-
geranylation
-
regiospecific
-
dmapp
- terreus
- dimethylallyltryptophan
-
hapalindole-type
-
aptase
- clorobiocin
- analysis
The enzyme appears in viruses and cellular organisms
Reaction Schemes
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
apT
aromatic prenyltransferase
PT-1
PT1L
aromatic prenyltransferase
-
-
ambiguous
-
PT-1
-
-
-
-
PT1L
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + a 2-acylphloroglucinol = diphosphate + a 2-acyl-4-prenylphloroglucinol
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:2-acylphloroglucinol 4-dimethylallyltransferase
The enzyme, characterized from hop (Humulus lupulus), acts on phlorisovalerophenone, phlormethylbutanophenone, and phlorisobutanophenone during the synthesis of bitter acids. It also acts with much lower activity on naringenin chalcone. Forms a complex with EC 2.5.1.137, 2-acyl-4-prenylphloroglucinol 6-prenyltransferase, which catalyses additional prenylation reactions. Requires Mg2+.
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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
dimethylallyl diphosphate + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
dimethylallyl diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
diphosphate + 3,5-dihydroxy-4,4-bis(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one
dimethylallyl diphosphate + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
dimethylallyl diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
diphosphate + 3,5-dihydroxy-2-(3-methylbutanoyl)-4,4-bis(3-methylbut-2-en-1-yl)cyclohexa-2,5-dien-1-one
dimethylallyl diphosphate + naringenin chalcone
diphosphate + desmethylxanthohumol
-
-
-
?
dimethylallyl diphosphate + phenyl(2,4,6-trihydroxyphenyl)methanone
diphosphate + phenyl[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methanone
dimethylallyl diphosphate + phenyl[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methanone
diphosphate + 2-benzoyl-3,5-dihydroxy-4,4-bis(3-methylbut-2-en-1-yl)cyclohexa-2,5-dien-1-one
-
-
-
?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
dimethylallyl diphosphate + phlormethylbutanophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
29.5% of the activity with phlorisovalerophenone
-
-
?
farnesyl diphosphate + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]phenyl]propan-1-one
-
-
-
?
farnesyl diphosphate + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]phenyl]butan-1-one
-
-
-
?
farnesyl diphosphate + phenyl(2,4,6-trihydroxyphenyl)methanone
diphosphate + phenyl[2,4,6-trihydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]phenyl]methanone
-
-
-
?
geranyl diphosphate + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
diphosphate + 1-[3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4,6-trihydroxyphenyl]-2-methylpropan-1-one
-
-
-
?
geranyl diphosphate + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
diphosphate + 1-[3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4,6-trihydroxyphenyl]-3-methylbutan-1-one
-
-
-
?
geranyl diphosphate + phenyl(2,4,6-trihydroxyphenyl)methanone
diphosphate + [3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4,6-trihydroxyphenyl](phenyl)methanone
-
-
-
?
geranyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-geranylphenyl]propan-1-one
-
-
-
?
dimethylallyl diphosphate + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
-
-
-
?
dimethylallyl diphosphate + 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
-
-
-
?
dimethylallyl diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
diphosphate + 3,5-dihydroxy-4,4-bis(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one
-
-
-
?
dimethylallyl diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
diphosphate + 3,5-dihydroxy-4,4-bis(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one
-
-
-
?
dimethylallyl diphosphate + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
-
-
-
?
dimethylallyl diphosphate + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
-
-
-
?
dimethylallyl diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
diphosphate + 3,5-dihydroxy-2-(3-methylbutanoyl)-4,4-bis(3-methylbut-2-en-1-yl)cyclohexa-2,5-dien-1-one
-
-
-
?
dimethylallyl diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
diphosphate + 3,5-dihydroxy-2-(3-methylbutanoyl)-4,4-bis(3-methylbut-2-en-1-yl)cyclohexa-2,5-dien-1-one
-
-
-
?
dimethylallyl diphosphate + phenyl(2,4,6-trihydroxyphenyl)methanone
diphosphate + phenyl[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methanone
-
-
-
?
dimethylallyl diphosphate + phenyl(2,4,6-trihydroxyphenyl)methanone
diphosphate + phenyl[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methanone
-
-
-
?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
-
-
-
-
?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
-
-
-
?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
61.9% of the activity with phlorisovalerophenone
-
-
?
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
-
-
-
-
?
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
-
-
-
?
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
best substrate
-
-
?
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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
dimethylallyl diphosphate + naringenin chalcone
diphosphate + desmethylxanthohumol
-
-
-
?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
61.9% of the activity with phlorisovalerophenone
-
-
?
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
best substrate
-
-
?
dimethylallyl diphosphate + phlormethylbutanophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
29.5% of the activity with phlorisovalerophenone
-
-
?
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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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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.42
3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
0.16
2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
with dimethylallyl diphosphate as cosubstrate, at pH 7.5 and 37°C
0.38
2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
0.0435
dimethylallyl diphosphate
truncated recombinant protein, pH 7.0, 30°C
0.0436
dimethylallyl diphosphate
presence of prenyltransferase PT2, pH 7.0, 30°C
0.071
dimethylallyl diphosphate
with 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one as cosubstrate, at pH 7.5 and 37°C
0.0057
geranyl diphosphate
truncated recombinant protein, pH 7.0, 30°C
0.00618
geranyl diphosphate
presence of prenyltransferase PT2, pH 7.0, 30°C
0.46
geranyl diphosphate
with phenyl(2,4,6-trihydroxyphenyl)methanone as cosubstrate, at pH 7.5 and 37°C
0.47
phenyl(2,4,6-trihydroxyphenyl)methanone
with geranyl diphosphate as cosubstrate, at pH 7.5 and 37°C
-
0.7
phenyl(2,4,6-trihydroxyphenyl)methanone
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
-
0.0051
phlorisobutyrophenone
truncated recombinant protein, pH 7.0, 30°C
0.00668
phlorisobutyrophenone
presence of prenyltransferase PT2, pH 7.0, 30°C
0.00136
phlorisovalerophenone
truncated recombinant protein, pH 7.0, 30°C
0.00339
phlorisovalerophenone
presence of prenyltransferase PT2, pH 7.0, 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.012
3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
0.014
2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
0.284
2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
with dimethylallyl diphosphate as cosubstrate, at pH 7.5 and 37°C
0.27
dimethylallyl diphosphate
with 1 as cosubstrate, at pH 7.5 and 37°C
0.27
dimethylallyl diphosphate
with 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one as cosubstrate, at pH 7.5 and 37°C
0.126
geranyl diphosphate
with 3 as cosubstrate, at pH 7.5 and 37°C
0.126
geranyl diphosphate
with phenyl(2,4,6-trihydroxyphenyl)methanone as cosubstrate, at pH 7.5 and 37°C
0.012
phenyl(2,4,6-trihydroxyphenyl)methanone
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
-
0.137
phenyl(2,4,6-trihydroxyphenyl)methanone
with geranyl diphosphate as cosubstrate, at pH 7.5 and 37°C
-
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0286
3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
3.8169
dimethylallyl diphosphate
with 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one as cosubstrate, at pH 7.5 and 37°C
0.2739
geranyl diphosphate
with phenyl(2,4,6-trihydroxyphenyl)methanone as cosubstrate, at pH 7.5 and 37°C
0.0368
2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
1.775
2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
with dimethylallyl diphosphate as cosubstrate, at pH 7.5 and 37°C
0.0171
phenyl(2,4,6-trihydroxyphenyl)methanone
with farnesyl diphosphate as cosubstrate, at pH 7.5 and 37°C
-
0.2915
phenyl(2,4,6-trihydroxyphenyl)methanone
with geranyl diphosphate as cosubstrate, at pH 7.5 and 37°C
-
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pH OPTIMUM
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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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
coexpression of codon-optimized prenyltransferases PT1L and PT2 in yeast leads to the production of bitter acids. PT1L/PT2 forms and functions as a complex in membranes. PT1L catalyzes the first prenylation step, and PT2 catalyzes the two subsequent prenylation steps
physiological function
PT-1 catalyzes the first transfer of dimethylallyl moiety to phloroglucinol derivatives, phlorisovalerophenone, phlorisobutyrophenone and phlormethylbutanophenone, leading to the formation of humulone and lupulone derivatives, i.e. Humulus lupulus bitter acids. PT-1 also recognizes naringenin chalcone as a flavonoid substrate to yield xanthohumol
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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). PT1_HUMLU
411
8
45481
Swiss-Prot
Chloroplast (Reliability: 2)
PT1L_HUMLU
414
8
45929
Swiss-Prot
Chloroplast (Reliability: 2)
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
mutation of the Asp in Asp-rich motifs in PT1L to Ala and coexpression with wild-type prenyltransferase, the mutant strain does not produce any prenylated products. A truncated variant lacking 83 amino acid from the start codon, displays much higher activity than wild-type
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
-
HPLC assay for the prenylation reactions, measuring enzyme activities measured in protein extracts from hop flowerbudsflowers and young cones
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Tsurumaru, Y.; Sasaki, K.; Miyawaki, T.; Uto, Y.; Momma, T.; Umemoto, N.; Momose, M.; Yazaki, K.
HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops
Biochem. Biophys. Res. Commun.
417
393-398
2012
Humulus lupulus (E5RP65)
brenda
Zuurbier, K.; Fung, S.; Scheffer, J.; Verpoorte, R.
In-vitro prenylation of aromatic intermediates in the biosynthesis of bitter acids in Humulus lupulus
Phytochemistry
49
2315-2322
1998
Humulus lupulus
-
brenda
Tsurumaru, Y.; Sasaki, K.; Miyawaki, T.; Momma, T.; Umemoto, N.; Yazaki, K.
An aromatic prenyltransferase-like gene HlPT-1 preferentially expressed in lupulin glands of hop
Plant Biotechnol.
27
199-204
2010
Humulus lupulus (E5RP65)
-
brenda
Li, H.; Ban, Z.; Qin, H.; Ma, L.; King, A.J.; Wang, G.
A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway
Plant Physiol.
167
650-659
2015
Humulus lupulus (A0A0B5A051)
brenda
Zhou, K.; Wunsch, C.; Dai, J.; Li, S.M.
gem-Diprenylation of acylphloroglucinols by a fungal prenyltransferase of the dimethylallyltryptophan synthase superfamily
Org. Lett.
19
388-391
2017
Aspergillus terreus (A0A1B0UHJ4), Aspergillus terreus DSM 1958 (A0A1B0UHJ4)
brenda
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