Reaction participants Show >> << Hide
- Name help_outline an α-Kdo-(2→4)-α-Kdo-(2→6)-(acyl)-lipid IVA Identifier CHEBI:176430 Charge -6 Formula C41H55N2O38P2R5 SMILEShelp_outline [C@H]1(OP(=O)([O-])[O-])[C@H](OC(=O)C[C@@H](*)O)[C@@H](NC(=O)C[C@@H](*)OC(=O)*)[C@@H](O[C@@H]1CO[C@@]2(C(=O)[O-])O[C@@H]([C@H](O)[C@@H](C2)O[C@@]3(C(=O)[O-])O[C@@H]([C@H](O)[C@@H](C3)O)[C@@H](CO)O)[C@@H](CO)O)OC[C@@H]4[C@H]([C@@H]([C@H]([C@H](O4)OP(=O)([O-])[O-])NC(=O)C[C@@H](*)O)OC(=O)C[C@@H](*)O)O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
a fatty acyl-[ACP]
Identifier
RHEA-COMP:14125
Reactive part
help_outline
- Name help_outline O-(S-fatty acylpantetheine-4ʼ-phosphoryl)-L-serine residue Identifier CHEBI:138651 Charge -1 Formula C15H24N3O9PSR SMILEShelp_outline C(NC(CCNC(=O)[C@@H](C(COP(OC[C@@H](C(*)=O)N*)(=O)[O-])(C)C)O)=O)CSC(*)=O 2D coordinates Mol file for the small molecule Search links Involved in 16 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an α-Kdo-(2→4)-α-Kdo-(2→6)-lipid A Identifier CHEBI:176431 Charge -6 Formula C42H54N2O39P2R6 SMILEShelp_outline [C@H]1(OP(=O)([O-])[O-])[C@H](OC(=O)C[C@@H](*)OC(*)=O)[C@@H](NC(=O)C[C@@H](*)OC(=O)*)[C@@H](O[C@@H]1CO[C@@]2(C(=O)[O-])O[C@@H]([C@H](O)[C@@H](C2)O[C@@]3(C(=O)[O-])O[C@@H]([C@H](O)[C@@H](C3)O)[C@@H](CO)O)[C@@H](CO)O)OC[C@@H]4[C@H]([C@@H]([C@H]([C@H](O4)OP(=O)([O-])[O-])NC(=O)C[C@@H](*)O)OC(=O)C[C@@H](*)O)O 2D coordinates Mol file for the small molecule Search links Involved in 9 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
holo-[ACP]
Identifier
RHEA-COMP:9685
Reactive part
help_outline
- Name help_outline O-(pantetheine-4ʼ-phosphoryl)-L-serine residue Identifier CHEBI:64479 Charge -1 Formula C14H25N3O8PS SMILEShelp_outline C(NC(CCNC(=O)[C@@H](C(COP(OC[C@@H](C(*)=O)N*)(=O)[O-])(C)C)O)=O)CS 2D coordinates Mol file for the small molecule Search links Involved in 196 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:69400 | RHEA:69401 | RHEA:69402 | RHEA:69403 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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| EC numbers help_outline | ||||
| MetaCyc help_outline |
Related reactions help_outline
Specific form(s) of this reaction
Publications
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Function of the Escherichia coli msbB gene, a multicopy suppressor of htrB knockouts, in the acylation of lipid A. Acylation by MsbB follows laurate incorporation by HtrB.
Clementz T., Zhou Z., Raetz C.R.H.
Overexpression of the Escherichia coli msbB gene on high copy plasmids suppresses the temperature-sensitive growth associated with mutations in the htrB gene. htrB encodes the lauroyl transferase of lipid A biosynthesis that acylates the intermediate (Kdo)2-lipid IVA (Brozek, K. A., and Raetz, C. ... >> More
Overexpression of the Escherichia coli msbB gene on high copy plasmids suppresses the temperature-sensitive growth associated with mutations in the htrB gene. htrB encodes the lauroyl transferase of lipid A biosynthesis that acylates the intermediate (Kdo)2-lipid IVA (Brozek, K. A., and Raetz, C. R. H. (1990) J. Biol. Chem. 265, 15410-15417). Since msbB displays 27.5% identity and 42.2% similarity to htrB, we explored the possibility that msbB encodes a related acyltransferase. In contrast to htrB, extracts of strains with insertion mutations in msbB are not defective in transferring laurate from lauroyl acyl carrier protein to (Kdo)2-lipid IVA. However, extracts of msbB mutants do not efficiently acylate the product formed by HtrB, designated (Kdo)2-(lauroyl)-lipid IVA. Extracts of strains harboring msbB+ bearing plasmids acylate (Kdo)2-(lauroyl)-lipid IVA very rapidly compared with wild type. We solubilized and partially purified MsbB from an overproducing strain, lacking HtrB. MsbB transfers myristate or laurate, activated on ACP, to (Kdo)2-(lauroyl)-lipid IVA. Decanoyl, palmitoyl, palmitoleoyl, and (R)-3-hydroxymyristoyl-ACP are poor acyl donors. MsbB acylates (Kdo)2-(lauroyl)-lipid IVA about 100 times faster than (Kdo)2-lipid IVA. The slow, but measurable, rate whereby MsbB acts on (Kdo)2-lipid IVA may explain why overexpression of MsbB suppresses the temperature-sensitive phenotype of htrB mutations. Presumably, the acyloxyacyl group generated by excess MsbB substitutes for the one normally formed by HtrB. << Less
J. Biol. Chem. 272:10353-10360(1997) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.