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Your query returned 10 entries. Printable version
EC | 2.3.1.261 | ||||||||||
Accepted name: | (4-hydroxyphenyl)alkanoate synthase | ||||||||||
Reaction: | (1) 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 (2) 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 |
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Other name(s): | msl7 (gene name); Pks15/1 | ||||||||||
Systematic name: | malonyl-CoA:4-hydroxybenzoyl-[(4-hydroxyphenyl)alkanoate synthase] malonyltransferase [(4-hydroxyphenyl)alkanoate-forming] | ||||||||||
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 [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. | ||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | ||||||||||
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EC | 2.3.1.282 | ||||||||||
Accepted name: | phenolphthiocerol/phthiocerol/phthiodiolone dimycocerosyl transferase | ||||||||||
Reaction: | (1) 2 a mycocerosyl-[mycocerosic acid synthase] + a phthiocerol = a dimycocerosyl phthiocerol + 2 holo-[mycocerosic acid synthase] (2) 2 a mycocerosyl-[mycocerosic acid synthase] + a phthiodiolone = a dimycocerosyl phthiodiolone + 2 holo-[mycocerosic acid synthase] (3) 2 a mycocerosyl-[mycocerosic acid synthase] + a phenolphthiocerol = a dimycocerosyl phenolphthiocerol + 2 holo-[mycocerosic acid synthase] |
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Glossary: | a mycocerosate = 2,4,6-trimethyl- and 2,4,6,8-tetramethyl-2-alkanoic acids present in many pathogenic mycobacteria. The chiral centers bearing the methyl groups have an L (levorotatory) stereo configuration. a phthiocerol = a linear carbohydrate molecule to which one methoxyl group, one methyl group, and two secondary hydroxyl groups are attached. a phthiodiolone = an intermediate in phthiocerol biosynthesis, containing an oxo group where phthiocerols contain a methoxyl group a phenolphthiocerol = a compound related to phthiocerol that contains a phenol group at the ω end of the molecule |
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Other name(s): | papA5 (gene name) | ||||||||||
Systematic name: | mycocerosyl-[mycocerosic acid synthase]:phenolphthiocerol/phthiocerol/phthiodiolone dimycocerosyl transferase | ||||||||||
Comments: | The enzyme, present in certain pathogenic species of mycobacteria, catalyses the transfer of mycocerosic acids to the two hydroxyl groups at the common lipid core of phthiocerol, phthiodiolone, and phenolphthiocerol, forming dimycocerosate esters. The fatty acid precursors of mycocerosic acids are activated by EC 6.2.1.49, long-chain fatty acid adenylyltransferase FadD28, which loads them onto EC 2.3.1.111, mycocerosate synthase. That enzyme extends the precursors to form mycocerosic acids that remain attached until transferred by EC 2.3.1.282. | ||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB | ||||||||||
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EC | 2.3.1.292 | ||||||||||
Accepted name: | (phenol)carboxyphthiodiolenone synthase | ||||||||||
Reaction: | (1) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + icosanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C32-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O (2) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + docosanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C34-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O (3) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + 19-(4-hydroxyphenyl)-nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C37-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O (4) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + 17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C35-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O |
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Glossary: | C32-carboxyphthiodiolenone = (4E,9R,11R)-9,11-dihydroxy-2,4-dimethyl-3-oxotriacont-4-enoate C34-carboxyphthiodiolenone = (4E,9R,11R)-9,11-dihydroxy-2,4-dimethyl-3-oxodotriacont-4-enoate C35-phenolcarboxyphthiodiolenone = (4E)-9,11-dihydroxy-27-(4-hydroxyphenyl)-2,4-dimethyl-3-oxoheptacos-4-enoate C37-phenolcarboxyphthiodiolenone = (4E,9R,11R)-9,11-dihydroxy-29-(4-hydroxyphenyl)-2,4-dimethyl-3-oxononacos-4-enoate phthiocerols = linear carbohydrates containing one methoxyl group, one methyl group, and two secondary hydroxyl groups that serve as a backbone for certain lipids and glycolipids found in many species of Mycobacteriaceae |
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Other name(s): | ppsABCDE (gene names) | ||||||||||
Systematic name: | (methyl)malonyl-CoA:long-chain acyl-[(phenol)carboxyphthiodiolenone synthase] (methyl)malonyltransferase {carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase]-forming} | ||||||||||
Comments: | The enzyme, which is a complex of five polyketide synthase proteins, is involved in the synthesis of the lipid core common to phthiocerols and phenolphthiocerols. The first protein, PpsA, can accept either a C18 or C20 long-chain fatty acyl, or a (4-hydroxyphenyl)-C17 or C19 fatty acyl. The substrates must first be adenylated by EC 6.2.1.59, long-chain fatty acid adenylase/transferase FadD26, which also loads them onto PpsA. PpsA then extends them using a malonyl-CoA extender unit. The PpsB protein adds the next malonyl-CoA extender unit. The absence of a dehydratase and an enoyl reductase domains in the PpsA and PpsB modules results in the formation of the diol portion of the phthiocerol moiety. PpsC adds a third malonyl unit (releasing a water molecule due to its dehydratase domain), PpsD adds an (R)-methylmalonyl unit, releasing a water molecule, and PpsE adds a second (R)-methylmalonyl unit, without releasing a water molecule. The incorporation of the methylmalonyl units results in formation of two branched methyl groups in the elongated product. The enzyme does not contain a thioesterase domain [2], and release of the products requires the tesA-encoded type II thioesterase [1]. | ||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB | ||||||||||
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EC | 2.7.7.94 | ||||||||||
Transferred entry: | 4-hydroxyphenylalkanoate adenylyltransferase. Now EC 6.2.1.51, 4-hydroxyphenylalkanoate adenylyltransferase FadD29 | ||||||||||
EC | 2.7.7.95 | ||||||||||
Transferred entry: | mycocerosic acid adenylyltransferase. Now EC 6.2.1.49, long-chain fatty acid adenylyltransferase FadD28 | ||||||||||
EC | 2.7.7.98 | ||||||||||
Transferred entry: | 4-hydroxybenzoate adenylyltransferase. Now EC 6.2.1.50, 4-hydroxybenzoate adenylyltransferase FadD22 | ||||||||||
EC | 6.2.1.49 | ||||||||||
Accepted name: | long-chain fatty acid adenylyltransferase FadD28 | ||||||||||
Reaction: | ATP + a long-chain fatty acid + holo-[mycocerosate synthase] = AMP + diphosphate + a long-chain acyl-[mycocerosate synthase] (overall reaction) (1a) ATP + a long-chain fatty acid = diphosphate + a long-chain acyl-adenylate ester (1b) a long-chain acyl-adenylate ester + holo-[mycocerosate synthase] = AMP + a long-chain acyl-[mycocerosate synthase] |
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Other name(s): | fadD28 (gene name) | ||||||||||
Systematic name: | long-chain fatty acid:holo-[mycocerosate synthase] ligase (AMP-forming) | ||||||||||
Comments: | The enzyme, found in certain mycobacteria, activates long-chain fatty acids by adenylation and transfers them to EC 2.3.1.111, mycocerosate synthase. The enzyme participates in the biosynthesis of the virulent lipids dimycocerosates (DIM) and dimycocerosyl triglycosyl phenolphthiocerol (PGL). | ||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB | ||||||||||
References: |
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EC | 6.2.1.50 | ||||||||||
Accepted name: | 4-hydroxybenzoate adenylyltransferase FadD22 | ||||||||||
Reaction: | ATP + 4-hydroxybenzoate + holo-[4-hydroxyphenylalkanoate synthase] = AMP + diphosphate + 4-hydroxybenzoyl-[4-hydroxyphenylalkanoate synthase] (overall reaction) (1a) ATP + 4-hydroxybenzoate = 4-hydroxybenzoyl-adenylate + diphosphate (1b) 4-hydroxybenzoyl-adenylate + holo-[4-hydroxyphenylalkanoate synthase] = AMP + 4-hydroxybenzoyl-[4-hydroxyphenylalkanoate synthase] |
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Other name(s): | fadD22 (gene name); 4-hydroxybenzoate adenylase | ||||||||||
Systematic name: | 4-hydroxybenzoate:holo-[4-hydroxyphenylalkanoate synthase] ligase (AMP-forming) | ||||||||||
Comments: | This mycobacterial enzyme participates in the biosynthesis of phenolphthiocerols. Following the substrate’s activation by adenylation, it is transferred to an acyl-carrier protein domain within the enzyme, from which it is transferred to EC 2.3.1.261, 4-hydroxyphenylalkanoate synthase. | ||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | ||||||||||
References: |
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EC | 6.2.1.51 | ||||||||||
Accepted name: | 4-hydroxyphenylalkanoate adenylyltransferase FadD29 | ||||||||||
Reaction: | (1) ATP + 17-(4-hydroxyphenyl)heptadecanoate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + diphosphate + 17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase] (1a) ATP + 17-(4-hydroxyphenyl)heptadecanoate = diphosphate + 17-(4-hydroxyphenyl)heptadecanoyl-adenylate (1b) 17-(4-hydroxyphenyl)heptadecanoyl-adenylate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + 17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase] (2) ATP + 19-(4-hydroxyphenyl)nonadecanoate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + diphosphate + 19-(4-hydroxyphenyl)nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase] (2a) ATP + 19-(4-hydroxyphenyl)nonadecanoate = diphosphate + 19-(4-hydroxyphenyl)nonadecanoyl-adenylate (2b) 19-(4-hydroxyphenyl)nonadecanoyl-adenylate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + 19-(4-hydroxyphenyl)nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase] |
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Other name(s): | fadD29 (gene name); 4-hydroxyphenylalkanoate adenylase | ||||||||||
Systematic name: | 4-hydroxyphenylalkanoate:holo-[(phenol)carboxyphthiodiolenone synthase] ligase | ||||||||||
Comments: | The mycobacterial enzyme participates in the biosynthesis of phenolphthiocerols. Following the substrate’s activation by adenylation, it is transferred to an acyl-carrier protein domain within the enzyme, from which it is transferred to the phenolphthiocerol/phthiocerol polyketide synthase. | ||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | ||||||||||
References: |
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EC | 6.2.1.59 | ||||||||||
Accepted name: | long-chain fatty acid adenylase/transferase FadD26 | ||||||||||
Reaction: | ATP + a long-chain fatty acid + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + diphosphate + a long-chain acyl-[(phenol)carboxyphthiodiolenone synthase] (overall reaction) (1a) ATP + a long-chain fatty acid = diphosphate + a long-chain fatty-acyl adenylate ester (1b) a long-chain fatty-acyl adenylate ester + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + a long-chain acyl-[(phenol)carboxyphthiodiolenone synthase] |
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Glossary: | phthiocerols = linear carbohydrates containing one methoxyl group, one methyl group, and two secondary hydroxyl groups that serve as a backbone for certain lipids and glycolipids found in many species of Mycobacteriaceae arachidate = icosanoate behenate = docosanoate lignocerate= tetracosanoate |
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Other name(s): | FadD26 | ||||||||||
Systematic name: | long-chain fatty acid:holo-[(phenol)carboxyphthiodiolenone synthase] ligase (AMP-forming) | ||||||||||
Comments: | The enzyme, present in pathogenic species of mycobacteria, participates in the pathway for biosynthesis of phthiocerols. It catalyses the adenylation of the long-chain fatty acids arachidate (C20) or behenate (C22) [1] and potentially the very-long-chain fatty acid lignocerate (C24) [2]. The activated fatty acids are then loaded to EC 2.3.1.292, (phenol)carboxyphthiodiolenone synthase. | ||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | ||||||||||
References: |
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