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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.
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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
Substrates: -
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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
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additional information
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additional information
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Substrates: development of a rapid PCR assay to characterize the intact pks15/1 gene, overview
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additional information
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Substrates: development of a rapid PCR assay to characterize the intact pks15/1 gene, overview
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additional information
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Substrates: development of a rapid PCR assay to characterize the intact pks15/1 gene, overview
Products: -
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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
Substrates: -
Products: -
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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
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Infections
A case of childhood tuberculosis from late mediaeval Somerset, England.
Infections
Molecular analysis of Mycobacterium tuberculosis strains with an intact pks15/1 gene in a rural community of Mexico.
Tuberculosis
A rapid PCR assay to characterize the intact pks15/1 gene, a virulence marker in Mycobacterium tuberculosis.
Tuberculosis
Characterisation of pks15/1 in clinical isolates of Mycobacterium tuberculosis from Mexico.
Tuberculosis
Draft Genome Sequences of Mycobacterium tuberculosis Clinical Isolates from the Ural Region of Russia That Carry the pks15/1 Gene.
Tuberculosis
Genetic diversity of Mycobacterium tuberculosis isoniazid monoresistant and multidrug-resistant in Rio Grande do Sul, a tuberculosis high-burden state in Brazil.
Tuberculosis
Intact pks15/1 in non-W-Beijing Mycobacterium tuberculosis isolates.
Tuberculosis
Macro-array and bioinformatic analyses reveal mycobacterial 'core' genes, variation in the ESAT-6 gene family and new phylogenetic markers for the Mycobacterium tuberculosis complex.
Tuberculosis
Molecular analysis of Mycobacterium tuberculosis strains with an intact pks15/1 gene in a rural community of Mexico.
Tuberculosis
Multidrug-Resistant Mycobacterium tuberculosis of the Latin American Mediterranean Lineage, Wrongly Identified as Mycobacterium pinnipedii (Spoligotype International Type 863 [SIT863]), Causing Active Tuberculosis in South Brazil.
Tuberculosis
Revisiting the expression signature of pks15/1 unveils regulatory patterns controlling phenolphtiocerol and phenolglycolipid production in pathogenic mycobacteria.
Tuberculosis
Role of the pks15/1 gene in the biosynthesis of phenolglycolipids in the Mycobacterium tuberculosis complex. Evidence that all strains synthesize glycosylated p-hydroxybenzoic methly esters and that strains devoid of phenolglycolipids harbor a frameshift mutation in the pks15/1 gene.
Tuberculosis
The polyketide Pks1 contributes to biofilm formation in Mycobacterium tuberculosis.
Tuberculosis
[Analysis of chromosome deletions of TbDl, RD6 and pks15/1 in clinical strains of Mycobacterium tuberculosis]
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malfunction
the Dpks15 mutant has a slight reduction in radial growth and produces fewer spores compared to wild-type. Insect bioassays indicate the DELTApks15 mutant to be significantly reduced in virulence against beet armyworms compared to wild-type, which can be partially accounted for by its markedly decreased ability to survive phagocytosis. Total haemocyte count decreases sharply by 50fold from days 1-3 post-inoculation in insects infected with wild-type, compared to a 5fold decrease in the DELTApks15 mutant. The mutant also produces 3fold fewer hemolymph hyphal bodies than the wild-type. In co-culture studies with amoebae that have phagocytic ability similar to that of insect haemocytes, the mortality rate of amoebae engulfing DELTApks15 decreases by 72% during 48 h, and DELTApks15 CFU decrease by 83% compared to co-culture with the wild-type. Thus, the DELTApks15 mutant has a reduced ability to cope with phagocytosis and highly reduced virulence in an insect host
malfunction
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the Dpks15 mutant has a slight reduction in radial growth and produces fewer spores compared to wild-type. Insect bioassays indicate the DELTApks15 mutant to be significantly reduced in virulence against beet armyworms compared to wild-type, which can be partially accounted for by its markedly decreased ability to survive phagocytosis. Total haemocyte count decreases sharply by 50fold from days 1-3 post-inoculation in insects infected with wild-type, compared to a 5fold decrease in the DELTApks15 mutant. The mutant also produces 3fold fewer hemolymph hyphal bodies than the wild-type. In co-culture studies with amoebae that have phagocytic ability similar to that of insect haemocytes, the mortality rate of amoebae engulfing DELTApks15 decreases by 72% during 48 h, and DELTApks15 CFU decrease by 83% compared to co-culture with the wild-type. Thus, the DELTApks15 mutant has a reduced ability to cope with phagocytosis and highly reduced virulence in an insect host
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physiological function
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4-hydroxybenzoic acid-AMP ligase FadD22 catalyzes the activation of 4-hydroxybenzoic acid and its subsequent transfer onto PKS15/1, to yield 4-hydroxyphenylalkanoate. This latter lipid is then activated by 4-hydroxyphenylalkanoate adenylyltransferase FadD29 and transferred onto PpsA. Overview on biosynthesis of phthiocerol and phthiodiolone dimycocerosates
physiological function
a gene disruption mutant is not able to produce dimycocerosyl phthiocerol, although it can produce mycocerosic acids. The mutant is attenuated in a murine model, supporting the hypothesis that dimycocerosyl phthiocerol is a virulence factor
physiological function
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a single open reading frame for pks15/1 is found in Mycobacterium bovis BCG. Disruption of the pks15/1 gene leads to the abolition of the synthesis of type-specific phenolphthiocerol glycolipid
physiological function
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comparison of amino acid sequence homology relationships among the mas-like (msl) genes and their domain organization in Mycobacterium tuberculosis
physiological function
polyketide synthase gene pks1 is involved in the elongation of 4hydroxybenzoic 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 pks1
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
physiological function
the pks15/1 gene is a virulence marker in Mycobacterium tuberculosis
physiological function
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4-hydroxybenzoic acid-AMP ligase FadD22 catalyzes the activation of 4-hydroxybenzoic acid and its subsequent transfer onto PKS15/1, to yield 4-hydroxyphenylalkanoate. This latter lipid is then activated by 4-hydroxyphenylalkanoate adenylyltransferase FadD29 and transferred onto PpsA. Overview on biosynthesis of phthiocerol and phthiodiolone dimycocerosates
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physiological function
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the pks15/1 gene is a virulence marker in Mycobacterium tuberculosis
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physiological function
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a gene disruption mutant is not able to produce dimycocerosyl phthiocerol, although it can produce mycocerosic acids. The mutant is attenuated in a murine model, supporting the hypothesis that dimycocerosyl phthiocerol is a virulence factor
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additional information
the DELTApks15 mutant is disrupted by a single integration of the transformation cassette at the pks15 locus. Disruption vector construction and Agrobacterium tumefaciens strain EHA105-mediated transformation of Beauveria bassiana strain BCC2660, pks15 gene expression analysis in the disruptant mutant and in wild-type. Mutant DELTApks15 phenotype, overview
additional information
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the DELTApks15 mutant is disrupted by a single integration of the transformation cassette at the pks15 locus. Disruption vector construction and Agrobacterium tumefaciens strain EHA105-mediated transformation of Beauveria bassiana strain BCC2660, pks15 gene expression analysis in the disruptant mutant and in wild-type. Mutant DELTApks15 phenotype, overview
additional information
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the DELTApks15 mutant is disrupted by a single integration of the transformation cassette at the pks15 locus. Disruption vector construction and Agrobacterium tumefaciens strain EHA105-mediated transformation of Beauveria bassiana strain BCC2660, pks15 gene expression analysis in the disruptant mutant and in wild-type. Mutant DELTApks15 phenotype, overview
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Sirakova, T.D.; Thirumala, A.K.; Dubey, V.S.; Sprecher, H.; Kolattukudy, P.E.
The Mycobacterium tuberculosis pks2 gene encodes the synthase for the hepta- and octamethyl-branched fatty acids required for sulfolipid synthesis
J. Biol. Chem.
276
16833-16839
2001
Mycobacterium tuberculosis
brenda
Sirakova, T.D.; Dubey, V.S.; Cynamon, M.H.; Kolattukudy, P.E.
Attenuation of Mycobacterium tuberculosis by disruption of a mas-like gene or a chalcone synthase-like gene, which causes deficiency in dimycocerosyl phthiocerol synthesis
J. Bacteriol.
185
2999-3008
2003
Mycobacterium tuberculosis (P96285), Mycobacterium tuberculosis H37Rv (P96285)
brenda
Simeone, R.; Constant, P.; Guilhot, C.; Daffe, M.; Chalut, C.
Identification of the missing trans-acting enoyl reductase required for phthiocerol dimycocerosate and phenolglycolipid biosynthesis in Mycobacterium tuberculosis
J. Bacteriol.
189
4597-4602
2007
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
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
brenda
Toopaang, W.; Phonghanpot, S.; Punya, J.; Panyasiri, C.; Klamchao, K.; Wasuwan, R.; Srisuksam, C.; Sangsrakru, D.; Sonthirod, C.; Tangphatsornruang, S.; Tanticharoen, M.; Amnuaykanjanasin, A.
Targeted disruption of the polyketide synthase gene pks15 affects virulence against insects and phagocytic survival in the fungus Beauveria bassiana
Fungal Biol.
121
664-675
2017
Beauveria bassiana (A0A1W5T7B8), Beauveria bassiana, Beauveria bassiana BCC2660 (A0A1W5T7B8)
brenda
Zenteno-Cuevas, R.; Hernandez-Morales, R.; Perez-Navarro, L.; Muniz-Salazar, R.; Santiago-Garcia, J.
A rapid PCR assay to characterize the intact pks15/1 gene, a virulence marker in Mycobacterium tuberculosis
J. Microbiol. Methods
121
33-35
2016
Mycobacterium tuberculosis (A5U6V5), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (A5U6V5)
brenda
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