2.3.1.241: Kdo2-lipid IVA acyltransferase
This is an abbreviated version!
For detailed information about Kdo2-lipid IVA acyltransferase, go to the full flat file.
Word Map on EC 2.3.1.241
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2.3.1.241
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neisseria
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meningitidis
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meningococcal
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lipopolysaccharide
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bactericidal
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penta-acylated
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nomvs
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hexa-acylated
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endotoxic
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serogrouping
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poras
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lipooligosaccharide
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reactogenicity
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monophosphoryl
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underacylated
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detergent-treated
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2'-position
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tetra-acylated
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drug development
- 2.3.1.241
- neisseria
- meningitidis
- meningococcal
- lipopolysaccharide
-
bactericidal
-
penta-acylated
-
nomvs
-
hexa-acylated
-
endotoxic
-
serogrouping
- poras
- lipooligosaccharide
-
reactogenicity
-
monophosphoryl
-
underacylated
-
detergent-treated
-
2'-position
-
tetra-acylated
- drug development
Reaction
Synonyms
(Kdo)2-lipid IVA lauroyltransferase, alpha-Kdo-(2->4)-alpha-(2->6)-lipid IVA lauroyltransferase, dodecanoyl-[acyl-carrier protein]:alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA O-dodecanoyltransferase, dodecanoyl-[acyl-carrier protein]:Kdo2-lipid IVA O-dodecanoyltransferase, ESA02293, htrB, HtrB1, Kdo2-lipid IVA lauroyltransferase, lauroyl-[acyl-carrier protein]:Kdo2-lipid IVA O-lauroyltransferase, lipid A biosynthesis lauroyltransferase, LpxL, LpxL1, LpxL2, lpxL_1, lpxL_2, PA0011, PP_1735
ECTree
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Substrates Products
Substrates Products on EC 2.3.1.241 - Kdo2-lipid IVA acyltransferase
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REACTION DIAGRAM
a dodecanoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose
(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + an [acyl-carrier protein]
a dodecanoyl-[acyl-carrier protein] + Kdo2-lipid IVA
dodecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
a tetradecanoyl-[acyl-carrier protein] + Kdo2-lipid IVA
tetradecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
dodecanoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose
(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + an [acyl-carrier protein]
i.e. alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA. Kdo i.e. 3-deoxy-D-manno-octulosonic acid. The enzyme transfers laurate from lauroyl-acyl carrier protein to the 2'-R-3-hydroxymyristate moiety of the tetraacylated lipid A precursor Kdo2-lipid IVA. The enzyme catalyzes also a slow second acylation, generating Kdo2-(dilauroyl)-lipid IVA. The enzyme is capable of acylating lipid IVA in vitro. The specific activity with lipid IVA as the substrate is 6000fold lower than for Kdo2-lipid IVA. The presence of the Kdo disaccharide in the substrate accelerates laurate transfer by at least 3 orders of magnitude. The enzyme acylates the lipid A analogue 1-dephospho-Kdo2-lipid IVA with 10fold higher specific activity as compared to alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA. Lauroyl-CoA can serve as an alternative acyl donor. Decanoyl-CoA, and to a lesser extent myristoyl-CoA, also function as acyl donors at low concentrations with inhibition of acylation at higher concentrations. Palmitoyl-CoA is inefficiently utilized as an acyl donor, but some acylation is observed. R-3-hydroxymyristoyl-[acyl-carrier protein] and synthetic R-3-hydroxylauroylmethylphosphopantetheine are poor acyl chain donors
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a dodecanoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose
(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + an [acyl-carrier protein]
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LpxL transfers a C14:0 secondary acyl chain to the 2'-position of lipid A
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?
a dodecanoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose
(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + an [acyl-carrier protein]
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LpxL transfers a C14:0 secondary acyl chain to the 2'-position of lipid A
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?
a dodecanoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose
(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + an [acyl-carrier protein]
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a dodecanoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose
(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + an [acyl-carrier protein]
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i.e. alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA
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a dodecanoyl-[acyl-carrier protein] + (3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose
(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose + an [acyl-carrier protein]
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the purified enzyme rapidly incorporates one dodecanoate into alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA. The rate of dodecanoate incorporation is reduced by several orders of magnitude when either one or both Kdos are absent in the acceptor. The enzyme incorporates dodecanoate 38 times faster than decanoate or tetradecanoate, respectively. Transfer of palmitate, palmitoleate, or R-3-hydroxymyristate is very slow
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dodecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
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a dodecanoyl-[acyl-carrier protein] + Kdo2-lipid IVA
dodecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
LpxL1 transfers a C12:0 acyl chain to the 2-O at the (3R)-hydroxytetradecanoyl chain on the 2'-glucosaminyl moity of Kdo2-lipid IVA
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a dodecanoyl-[acyl-carrier protein] + Kdo2-lipid IVA
dodecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
LpxL1 transfers a C12:0 acyl chain to the 2-O at the (3R)-hydroxytetradecanoyl chain on the 2'-glucosaminyl moity of Kdo2-lipid IVA
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a dodecanoyl-[acyl-carrier protein] + Kdo2-lipid IVA
dodecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
acyltransferase encoded by PP_1735 catalyses the addition of the C12:0 chain to the 2'-position of lipid A in Pseudomonas putida
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tetradecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
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a tetradecanoyl-[acyl-carrier protein] + Kdo2-lipid IVA
tetradecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
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a tetradecanoyl-[acyl-carrier protein] + Kdo2-lipid IVA
tetradecanoyl-Kdo2-lipid IVA + an [acyl-carrier protein]
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isoform HtrB1 exclusively mediates the addition of the 2-hydroxylaurate in C-2 position of lipid IVaA, while HtrB2 adds the laurate in C-2' position
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additional information
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isoform HtrB1 exclusively mediates the addition of the 2-hydroxylaurate in C-2 position of lipid IVaA, while HtrB2 adds the laurate in C-2' position
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