Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 23000215Publication DOI: 10.1016/j.carres.2012.05.015Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: S. Drouillard sophie.drouillard
cermav.cnrs.fr
Institutions: Centre de recherche sur Macromolecules Vegetales (CERMAV-CNRS), BP 53, F-38041 Grenoble Cedex 9, France
The α-Gal epitope is a carbohydrate structure, Galα-3Galβ-4GlcNAc-R, expressed on glycoconjuguates in many mammals, but not in humans. Species that do not express this epitope have present in their serum large amounts of natural anti-Gal antibodies, which contribute to organ hyperacute rejection during xenotransplantation. We first describe the efficient conversion of lactose into isoglobotriaose (Galα-3Galβ-4Glc) using high cell density cultures of a genetically engineered Escherichia coli strain expressing the bovine gene for α-1,3-galactosyltransferase. Attempts to produce the Galili pentasaccharide (Galα-3Galβ-4GlcNAcβ-3Galβ-4Glc) by additionally expressing the Neisseria meningitis lgtA gene for β-1,3-N-acetylglucosaminyltransferase and the Helicobacter pylori gene for β-1,4-galactosyltransferase were unsuccessful and led to the formation of a series of long chain oligosaccharides formed by the repeated addition of the trisaccharide motif [Galβ-4GlcNAcβ-3Galα-3] onto a lacto-N-neotetraose primer. The replacement of LgtA by a more specific β-1,3-N-acetylglucosaminyltransferase from H. pylori, which was unable to glycosylate α-galactosides, prevented the formation of these unwanted compounds and allowed the successful formation of the Galili pentasaccharide and longer α-Gal epitopes.
Escherichia coli, Oligosaccharides, fermentation, Metabolic engineering, α-Gal epitope, a-Gal epitope
Structure type: oligomer
Location inside paper: p.83, p.89, fig.6, (1) isoGb3
Trivial name: isoglobotriaose
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
Enzymes that release or process the structure: α-1,3-galactosyltransferase (recombinant α-3GalT)
Synthetic data: enzymatic
Comments, role: genetically engineered strain Escherichia coli
Related record ID(s): 29490, 29491, 29492, 29493, 29494, 29495, 29496, 29497, 29498, 29499, 29500, 29501, 29502, 29503, 29504, 29505, 29506, 29507, 29508, 29509, 29510, 29511, 29512, 29513, 29514
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G57666OY
Show glycosyltransferases
NMR conditions: in D2O at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3 aDGalp 96.64 69.44 70.51 70.34 72.05 62.14
4 bDGalp 104.05 70.82 78.37 66.03 76.29 62.24
aDGlcp 93.05 72.34 72.73 79.84 71.29 61.22
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3 aDGalp 5.17 3.88 ? 4.06 4.23 ?
4 bDGalp 4.55 3.69 3.82 4.22 ? ?
aDGlcp 5.25 3.61 ? 3.72 ? ?
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3 aDGalp 96.64/5.17 69.44/3.88 70.51/? 70.34/4.06 72.05/4.23 62.14/?
4 bDGalp 104.05/4.55 70.82/3.69 78.37/3.82 66.03/4.22 76.29/? 62.24/?
aDGlcp 93.05/5.25 72.34/3.61 72.73/? 79.84/3.72 71.29/? 61.22/?
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3 | aDGalp | 5.17 | 3.88 | ? | 4.06 | 4.23 | ? |
| 4 | bDGalp | 4.55 | 3.69 | 3.82 | 4.22 | ? | ? |
| | aDGlcp | 5.25 | 3.61 | ? | 3.72 | ? | ? |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3 | aDGalp | 96.64 | 69.44 | 70.51 | 70.34 | 72.05 | 62.14 |
| 4 | bDGalp | 104.05 | 70.82 | 78.37 | 66.03 | 76.29 | 62.24 |
| | aDGlcp | 93.05 | 72.34 | 72.73 | 79.84 | 71.29 | 61.22 |
|
There is only one chemically distinct structure:
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