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Information on EC 2.3.1.261 - (4-hydroxyphenyl)alkanoate synthase

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EC Tree
IUBMB Comments
The enzyme is part of the biosynthetic pathway of phenolphthiocerol, a lipid that serves as a virulence factor of pathogenic mycobacteria. It catalyses the elongation of 4-hydroxybenzoate that is loaded on its acyl-carrier domain to form (4-hydroxyphenyl)alkanoate intermediates. The enzyme adds either 8 or 9 malonyl-CoA units, resulting in formation of 17-(4-hydroxyphenyl)heptadecanoate or 19-(4-hydroxyphenyl)nonadecanoate, respectively. As the enzyme lacks a thioesterase domain , the product remains loaded on the acyl-carrier domain at the end of catalysis, and has to be hydrolysed by an as-yet unknown mechanism.
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UNIPROT: P96284
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
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4-hydroxybenzoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
8
malonyl-CoA
+
16
NADPH
+
16
H+
=
17-(4-hydroxyphenyl)heptadecanoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
8
CO2
+
8
CoA
+
16
NADP+
+
8
H2O
4-hydroxybenzoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
8
+
16
+
16
=
17-(4-hydroxyphenyl)heptadecanoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
8
+
8
+
16
+
8
4-hydroxybenzoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
9
malonyl-CoA
+
18
NADPH
+
18
H+
+
holo-[(4-hydroxyphenyl)alkanoate synthase]
=
19-(4-hydroxyphenyl)nonadecanoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
9
CO2
+
9
CoA
+
18
NADP+
+
9
H2O
4-hydroxybenzoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
9
+
18
+
18
+
holo-[(4-hydroxyphenyl)alkanoate synthase]
=
19-(4-hydroxyphenyl)nonadecanoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
9
+
9
+
18
+
9
Synonyms
type i pks, pks15/1, pks15, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4-hydroxyphenylalkanoate synthase
-
-
-
-
msl7
-
-
-
-
Pks15/1
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-
SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:4-hydroxybenzoyl-[(4-hydroxyphenyl)alkanoate synthase] malonyltransferase [(4-hydroxyphenyl)alkanoate-forming]
The enzyme is part of the biosynthetic pathway of phenolphthiocerol, a lipid that serves as a virulence factor of pathogenic mycobacteria. It catalyses the elongation of 4-hydroxybenzoate that is loaded on its acyl-carrier domain to form (4-hydroxyphenyl)alkanoate intermediates. The enzyme adds either 8 or 9 malonyl-CoA units, resulting in formation of 17-(4-hydroxyphenyl)heptadecanoate or 19-(4-hydroxyphenyl)nonadecanoate, respectively. As the enzyme lacks a thioesterase domain [1], the product remains loaded on the acyl-carrier domain at the end of catalysis, and has to be hydrolysed by an as-yet unknown mechanism.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-hydroxybenzoyl-[4-hydroxyphenylalkanoate synthase] + 8 malonyl-CoA + 16 NADPH + 16 H+
17-(4-hydroxyphenyl)heptadecanoyl-[4-hydroxyphenylalkanoate synthase] + 8 CO2 + 8 CoA + 16 NADP+ + 8 H2O
show the reaction diagram
-
-
-
?
4-hydroxybenzoyl-[4-hydroxyphenylalkanoate synthase] + 9 malonyl-CoA + 18 NADPH + 18 H+ + holo-[4-hydroxyphenylalkanoate synthase]
19-(4-hydroxyphenyl)nonadecanoyl-[4-hydroxyphenylalkanoate synthase] + 9 CO2 + 9 CoA + 18 NADP+ + 9 H2O
show the reaction diagram
-
-
-
?
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
4-hydroxybenzoyl-[4-hydroxyphenylalkanoate synthase] + 8 malonyl-CoA + 16 NADPH + 16 H+
17-(4-hydroxyphenyl)heptadecanoyl-[4-hydroxyphenylalkanoate synthase] + 8 CO2 + 8 CoA + 16 NADP+ + 8 H2O
show the reaction diagram
-
-
-
?
4-hydroxybenzoyl-[4-hydroxyphenylalkanoate synthase] + 9 malonyl-CoA + 18 NADPH + 18 H+ + holo-[4-hydroxyphenylalkanoate synthase]
19-(4-hydroxyphenyl)nonadecanoyl-[4-hydroxyphenylalkanoate synthase] + 9 CO2 + 9 CoA + 18 NADP+ + 9 H2O
show the reaction diagram
-
-
-
?
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
polyketide synthase gene pks15 is involved in the elongation of 4-hydroxybenzoic acid derivatives to form p-hydroxyphenylalkanoates, which in turn are converted, presumably by the PpsA-E synthase, to phenolphthiocerol derivatives. All the strains of Mycobacterium tuberculosis examined and deficient in the production of phenolphthiocerol derivatives are natural mutants with a frameshift mutation in pks15
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
PKS15_MYCTU
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
496
0
51702
Swiss-Prot
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Constant, P.; Perez, E.; Malaga, W.; Laneelle, M.A.; Saurel, O.; Daffe, M.; Guilhot, C.
Role of the pks15/1 gene in the biosynthesis of phenolglycolipids in the Mycobacterium tuberculosis complex. Evidence that all strains synthesize glycosylated p-hydroxybenzoic methyl esters and that strains devoid of phenolglycolipids harbor a frameshift
J. Biol. Chem.
277
38148-38158
2002
Mycobacterium tuberculosis (P96284), Mycobacterium tuberculosis (P96285), Mycobacterium tuberculosis, Mycobacterium tuberculosis variant bovis
Manually annotated by BRENDA team