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Information on EC 2.5.1.136 - 2-acylphloroglucinol 4-prenyltransferase for references in articles please use BRENDA:EC2.5.1.136
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EC Tree
IUBMB 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+.
The expected taxonomic range for this enzyme is: Humulus lupulus
Synonyms
aromatic prenyltransferase, PT-1, PT1, PT1L,
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aromatic prenyltransferase
aromatic prenyltransferase
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ambiguous
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aromatic prenyltransferase
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aromatic prenyltransferase
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PT-1
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gene name
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PT1L
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gene name
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dimethylallyl diphosphate + a 2-acylphloroglucinol = diphosphate + a 2-acyl-4-prenylphloroglucinol
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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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dimethylallyl diphosphate + naringenin chalcone
diphosphate + desmethylxanthohumol
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-
?
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
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?
geranyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-geranylphenyl]propan-1-one
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-
-
?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
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-
-
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?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
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-
-
?
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
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?
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
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?
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
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?
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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?
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dimethylallyl diphosphate + naringenin chalcone
diphosphate + desmethylxanthohumol
E5RP65
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?
dimethylallyl diphosphate + phlorisobutyrophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
E5RP65
61.9% of the activity with phlorisovalerophenone
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?
dimethylallyl diphosphate + phlorisovalerophenone
diphosphate + 3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
E5RP65
best substrate
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?
dimethylallyl diphosphate + phlormethylbutanophenone
diphosphate + 2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]butan-1-one
E5RP65
29.5% of the activity with phlorisovalerophenone
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?
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Mg2+
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exclusive requirement for Mg2+
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0.0435 - 0.0436
dimethylallyl diphosphate
0.0057 - 0.00618
geranyl diphosphate
0.0051 - 0.00668
phlorisobutyrophenone
0.00136 - 0.00339
phlorisovalerophenone
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
0.0057
geranyl diphosphate
truncated recombinant protein, pH 7.0, 30°C
0.00618
geranyl diphosphate
presence of prenyltransferase PT2, pH 7.0, 30°C
0.0051
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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UniProt
brenda
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brenda
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UniProt
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female flower, high expression
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low expression
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brenda
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brenda
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sequence contains membrane-spanning domains
brenda
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sequence contains a transit peptide
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physiological function
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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
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
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PT1L_HUMLU
414
8
45929
Swiss-Prot
PT1_HUMLU
411
8
45481
Swiss-Prot
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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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expression in Saccharomyces cerevisiae
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analysis
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HPLC assay for the prenylation reactions, measuring enzyme activities measured in protein extracts from hop flowerbudsflowers and young cones
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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
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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)
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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
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2.5.1.136 2-acylphloroglucinol 4-prenyltransferase
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