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- Name help_outline 2-[(L-alanin-3-ylcarbamoyl)methyl]-2-hydroxybutanedioate Identifier CHEBI:142969 Charge -2 Formula C9H12N2O8 InChIKeyhelp_outline RACKNMPLNJKJHK-IGJIYHIXSA-L SMILEShelp_outline O=C(NC[C@H]([NH3+])C(=O)[O-])C[C@](CC(=O)[O-])(C([O-])=O)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,521 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 2-[(2-aminoethylcarbamoyl)methyl]-2-hydroxybutanedioate Identifier CHEBI:142970 Charge -1 Formula C8H13N2O6 InChIKeyhelp_outline KQWWDTIPDRWKGZ-QMMMGPOBSA-M SMILEShelp_outline O=C(NCC[NH3+])C[C@](CC(=O)[O-])(C([O-])=O)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CO2 Identifier CHEBI:16526 (CAS: 124-38-9) help_outline Charge 0 Formula CO2 InChIKeyhelp_outline CURLTUGMZLYLDI-UHFFFAOYSA-N SMILEShelp_outline O=C=O 2D coordinates Mol file for the small molecule Search links Involved in 1,006 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:59120 | RHEA:59121 | RHEA:59122 | RHEA:59123 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Molecular characterization of staphyloferrin B biosynthesis in Staphylococcus aureus.
Cheung J., Beasley F.C., Liu S., Lajoie G.A., Heinrichs D.E.
Siderophores are iron-scavenging molecules produced by many microbes. In general, they are synthesized using either non-ribosomal peptide synthetase (NRPS) or NRPS-independent siderophore (NIS) pathways. Staphylococcus aureus produces siderophores, of which the structures of staphyloferrin A and s ... >> More
Siderophores are iron-scavenging molecules produced by many microbes. In general, they are synthesized using either non-ribosomal peptide synthetase (NRPS) or NRPS-independent siderophore (NIS) pathways. Staphylococcus aureus produces siderophores, of which the structures of staphyloferrin A and staphyloferrin B are known. Recently, the NIS biosynthetic pathway for staphyloferrin A was characterized. Here we show that, in S. aureus, the previously identified sbn (siderophore biosynthesis) locus encodes enzymes required for the synthesis of staphyloferrin B, an alpha-hydroxycarboxylate siderophore comprised of l-2,3-diaminopropionic acid, citric acid, 1,2-diaminoethane and alpha-ketoglutaric acid. Staphyloferrin B NIS biosynthesis was recapitulated in vitro, using purified recombinant Sbn enzymes and the component substrates. In vitro synthesized staphyloferrin B readily promoted the growth of iron-starved S. aureus, via the ABC transporter SirABC. The SbnCEF synthetases and a decarboxylase, SbnH, were necessary and sufficient to produce staphyloferrin B in reactions containing component substrates l-2,3-diaminopropionic acid, citric acid and alpha-ketoglutaric acid. Since 1,2-diaminoethane was not required, this component of the siderophore arises from the SbnH-dependent decarboxylation of a 2,3-diaminoproprionic acid-containing intermediate. Liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) analyses of a series of enzyme reactions identified mass ions corresponding to biosynthetic intermediates, allowing for the first proposed biosynthetic pathway for staphyloferrin B. << Less
Mol. Microbiol. 74:594-608(2009) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.