Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 19019146Journal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: fenglu63
nankai.edu.cn
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, PR China
D-Fucofuranose (D-Fucf) is a component of Escherichia coli O52 O antigen. This uncommon sugar is also the sugar moiety of the anticancer drug - gilvocarcin V produced by many streptomycetes. In E. coli O52, rmlA, rmlB, fcf1 and fcf2 were proposed in a previous study by our group to encode the enzymes of the dTDP-d-Fucf (the nucleotide-activated form of d-Fucf) biosynthetic pathway. In this study, Fcf1 and Fcf2 from E. coli O52 were expressed, purified and assayed for their respective activities. Novel product peaks from enzyme-substrate reactions were detected by capillary electrophoresis and the structures of the product compounds were elucidated by electro-spray ionization mass spectrometry and nuclear magnetic resonance spectroscopy. Fcf1 was confirmed to be a dTDP-6-deoxy-d-xylo-hex-4-ulopyranose reductase for the conversion of dTDP-6-deoxy-d-xylo-hex-4-ulopyranose to dTDP-d-fucopyranose (dTDP-D-Fucp), and Fcf2 a dTDP-d-Fucp mutase for the conversion of dTDP-d-Fucp to dTDP-d-Fucf. The Km of Fcf1 for dTDP-6-deoxy-d-xylo-hex-4-ulopyranose was determined to be 0.38 mM, and of Fcf2 for dTDP-d-Fucp to be 3.43 mM. The functional role of fcf1 and fcf2 in the biosynthesis of E. coli O52 O antigen were confirmed by mutation and complementation tests. This is the first time that the biosynthetic pathway of dTDP-d-Fucf has been fully characterized.
biosynthesis, O antigen, Biosynthetic Pathways, Escherichia coli O52, D-Fucofuranose (D-Fucf)
Structure type: monomer
Location inside paper: p. 1359, fig. 1
Trivial name: dTDP-6-deoxy-D-xylohex-4-ulose, dTDP-4-keto-6-deoxy-α-D-glucose, dTDP-6-dideoxy-xylo-hexos-4-ulose, dTDP-6-deoxy-α-D-xylo-hex-4-ulose, dTDP-4-oxo-6-deoxy-α-D-glucose, dTDP-6-deoxy-D-xylo-hex-4-ulopyranose, dTDP-4-keto-6-deoxy-D-glucose, dTDP-4-keto-6-deoxyglucose
Compound class: nucleoside diphosphate sugar
Contained glycoepitopes: IEDB_138113,IEDB_196259
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, sugar analysis, ESI-MS, GLC, genetic methods, HPLC, capillary electrophoresis (CE)
Enzymes that release or process the structure: RmlB, dTDP-glucose 4.6-dehydratase
Biosynthesis and genetic data: genetic data, biochemical data
Synthetic data: enzymatic
Comments, role: Substrate for biosynthesis of dTDP-D-Fucf.
Related record ID(s): 20526, 21584, 21690, 22754, 23100, 23229, 23325, 23327, 23328, 24136
NCBI Taxonomy refs (TaxIDs): 562
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There is only one chemically distinct structure:
Found 
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