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

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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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Word Map
  • 2.3.1.261
  • tuberculosis
  • glycolipids
  • polyketide
  • spoligotyping
  • beijing
  • leprae
  • bovis
  • phenolphthiocerol
  • brazil
  • euro-american
  • dimycocerosate
  • phthiocerol
  • miru-vntr
  • mexico
  • sputum
  • marinum
  • p-hydroxybenzoic
The expected taxonomic range for this enzyme is: Mycobacterium tuberculosis complex
Reaction Schemes
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
+
18
+
18
+
holo-[(4-hydroxyphenyl)alkanoate synthase]
=
19-(4-hydroxyphenyl)nonadecanoyl-[(4-hydroxyphenyl)alkanoate synthase]
+
9
+
9
+
18
+
9
Synonyms
pks15/1, pks15, more
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
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
show the reaction diagram
(1)
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-
-
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
show the reaction diagram
(2)
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-
-
PATHWAY SOURCE
PATHWAYS
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