Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Salmonella enterica [ICD11:
XN5VC 
];
infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 15259369Publication DOI: 10.1023/b:biom.0000029432.69418.6aJournal NLM ID: 9208478Publisher: Dordrecht: Kluwer Academic Publishers
Correspondence: roderich.suessmuth
uni-tuebingen.de
Institutions: Institut für Organische Chemie, Universität Tübingen, Tübingen, Germany, Institut für Mikrobiologie, Universität Tübingen, Tübingen, Germany
Salmochelins represent novel carbohydrate containing catecholate siderophores, which are excreted by Salmonella enterica and uropathogenic Escherichia coli strains under low-iron stress. While previous analytical data showed salmochelins to contain 2,3-dihydroxybenzoyl-L-serine and glucose, the molecular structure remained elusive. Structure elucidation with electrospray ionization-Fourier transform ion cyclotron resonance-mass spectrometry (ESI-FTICR-MS), GC-MS and 2D-NMR now revealed that salmochelins are enterobactin-related compounds, which are beta-C-glucosylated at the 5-position of a 2,3-dihydroxybenzoyl residue. The key compound salmochelin S4 is a twofold beta-C-glucosylated enterobactin analogue. Comparison of partial structures of salmochelin with a C-glycosylated compound previously characterized by another group strongly suggest that salmochelins represent the long sought compounds termed Salmonella resistance factors (SRF) or pacifarins. Transformation of iro-genes into enterobactin-producing E. coli K12 confers the ability to produce salmochelins. A detailed analysis proved iroB to be the sole gene with glycosyltransferase activity necessary for salmochelin production. Salmochelins compared to enterobactin are the better siderophores in the presence of serum albumin. This may indicate for salmochelins a considerably more important role for pathogenic processes in certain Escherichia coli and Salmonella infections than formerly assigned to enterobactin. This conclusion is supported by the location of the iro genes on pathogenicity islands of uropathogenic E. coli strains.
Escherichia coli, Salmonella enterica, salmochelins, siderophores
Structure type: monomer ; 402.10416 [M-H]-
C
16H
21NO
11Location inside paper: p. 472, Fig. 1, SX
Trivial name: salmochelin SX
Compound class: C-glycoside
Contained glycoepitopes: IEDB_150900
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, DNA techniques, acid hydrolysis, ESI-ICR-MS, methanolysis, HPLC, extraction, CC, cell growth, spectrophotometry, derivatization, HPLC-ESI-MS
Enzymes that release or process the structure: iroB
Biosynthesis and genetic data: genetic data
Related record ID(s): 51104, 51105, 51106
NCBI Taxonomy refs (TaxIDs): 28901,
83333
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error