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Information on EC 2.5.1.117 - homogentisate solanesyltransferase and Organism(s) Chlamydomonas reinhardtii and UniProt Accession A1JHN0

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IUBMB Comments
Requires Mg2+ for activity. Part of the biosynthesis pathway of plastoquinol-9. The enzymes purified from the plant Arabidopsis thaliana and the alga Chlamydomonas reinhardtii are also active in vitro with unsaturated C10 to C20 prenyl diphosphates, producing main products that are not decarboxylated .
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Chlamydomonas reinhardtii
UNIPROT: A1JHN0
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The taxonomic range for the selected organisms is: Chlamydomonas reinhardtii
The enzyme appears in selected viruses and cellular organisms
Synonyms
athst, homogentisate solanesyltransferase, at3g11950, homogentisate prenyltransferase, more
SYSTEMATIC NAME
IUBMB Comments
all-trans-nonaprenyl diphosphate:homogentisate nonaprenyltransferase
Requires Mg2+ for activity. Part of the biosynthesis pathway of plastoquinol-9. The enzymes purified from the plant Arabidopsis thaliana and the alga Chlamydomonas reinhardtii are also active in vitro with unsaturated C10 to C20 prenyl diphosphates, producing main products that are not decarboxylated [2].
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + homogentisate
diphosphate + (3-(2E,6E)-farnesyl-2,5-dihydroxyphenyl)acetate
show the reaction diagram
-
no decarboxylation of product, 95% of the total prenylated reaction products formed are carboxylic acids
-
?
all-trans-nonaprenyl diphosphate + homogentisate
diphosphate + 2-methyl-6-all-trans-nonaprenylbenzene-1,4-diol + CO2
show the reaction diagram
geranyl diphosphate + homogentisate
diphosphate + (3-geranyl-2,5-dihydroxyphenyl)acetate
show the reaction diagram
-
no decarboxylation of product, 95% of the total prenylated reaction products formed are carboxylic acids
-
?
geranylgeranyl diphosphate + homogentisate
diphosphate + (3-geranylgeranyl-2,5-dihydroxyphenyl)acetate
show the reaction diagram
-
no decarboxylation of product, 95% of the total prenylated reaction products formed are carboxylic acids
-
?
solanesyl diphosphate + homogentisate
diphosphate + 2-methyl-6-all-trans-nonaprenylbenzene-1,4-diol + CO2
show the reaction diagram
-
-
-
?
solanesyl diphosphate + homogentisate
diphosphate + 2-methyl-6-solanesyl-1,4-benzoquinol + CO2
show the reaction diagram
-
-
-
?
additional information
?
-
enzyme uses not only solanesyl diphosphate but also short chain prenyl diphosphates of 10-20 carbon atoms as prenyl donors. With these donors, prenyl transfer is largely decoupled from decarboxylation, and thus the major products are 6-prenyl-1,4-benzoquinol-2-methylcarboxylates rather than 2-methyl-6-prenyl-1,4-benzoquinols. The 6-prenyl-1,4-benzoquinol-2-methylcarboxylates are not substrates for homogentisate prenyl transferase-catalyzed decarboxylation, and the enzyme kinetics associated with forming these products appears quite distinct from those for 2-methyl-6-prenyl-1,4-benzoquinol formation. A model for mechanism is as follows: prenyl diphosphate binds to homogentisate prenyl transferase to form at least two alternative complexes that go on to react differently with homogentisate and prenylate it either with or without it first being decarboxylated. It is supposed that solanesyl diphosphate binds tightly and preferentially in the mode that compels prenylation with decarboxylation
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
all-trans-nonaprenyl diphosphate + homogentisate
diphosphate + 2-methyl-6-all-trans-nonaprenylbenzene-1,4-diol + CO2
show the reaction diagram
the enzyme is involved in biosynthesis pathway of plastoquinol-9
-
-
?
solanesyl diphosphate + homogentisate
diphosphate + 2-methyl-6-solanesyl-1,4-benzoquinol + CO2
show the reaction diagram
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
haloxydine
almost complete inhibition at 0.5 mM. Haloxydine inhibition is uncompetitive with respect to farnsyl diphosphate and either mixed or competitive with respect to homogentisate
[2-((R)-1-phenyl-ethylamino)-1-phosphono-ethyl]-phosphonic acid
structural analogue and inhibitory mimic of farnesyl diphosphate
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.025
(2E,6E)-farnesyl diphosphate
pH 8.5, 28°C
0.04
homogentisate
pH 8.5, 28°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.038
haloxydine
pH 8.5, 28°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in plastoquinone 9 biosynthesis
physiological function
the enzyme is involved in biosynthesis pathway of plastoquinol-9
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
HSTC_CHLRE
370
6
39347
Swiss-Prot
Chloroplast (Reliability: 3)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Sadre, R.; Gruber, J.; Frentzen, M.
Characterization of homogentisate prenyltransferases involved in plastoquinone-9 and tocochromanol biosynthesis
FEBS Lett.
580
5357-5362
2006
Arabidopsis thaliana (Q9SF04), Arabidopsis thaliana, Chlamydomonas reinhardtii (A1JHN0), Chlamydomonas reinhardtii, Chlamydomonas reinhardtii CC-1690 (A1JHN0)
Manually annotated by BRENDA team
Sadre, R.; Frentzen, M.; Saeed, M.; Hawkes, T.
Catalytic reactions of the homogentisate prenyl transferase involved in plastoquinone-9 biosynthesis
J. Biol. Chem.
285
18191-18198
2010
Arabidopsis thaliana (Q1ACB3), Chlamydomonas reinhardtii (A1JHN0), Spinacia oleracea
Manually annotated by BRENDA team
Liu, M.; Lu, S.
Plastoquinone and ubiquinone in plants Biosynthesis, physiological function and metabolic engineering
Front. Plant Sci.
7
1898
2016
Chlamydomonas reinhardtii (A1JHN0), Arabidopsis thaliana (Q1ACB3)
Manually annotated by BRENDA team