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1. Compound ID: 11172
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_146694,IEDB_149144,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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2. Compound ID: 11173
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-a-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_146694,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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3. Compound ID: 11174
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-a-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_146694,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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4. Compound ID: 11175
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_146694,IEDB_149144,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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5. Compound ID: 11176
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_146694,IEDB_149144,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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6. Compound ID: 11177
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-a-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_146694,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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7. Compound ID: 11178
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-a-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_146694,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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8. Compound ID: 11179
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_146694,IEDB_149144,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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9. Compound ID: 11182
|
a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-a-D-Glcp |
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Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_146694,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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10. Compound ID: 11183
|
a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130646,IEDB_130649,IEDB_130697,IEDB_135813,IEDB_135815,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140109,IEDB_140110,IEDB_140122,IEDB_141496,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_146694,IEDB_149144,IEDB_149558,IEDB_151528,IEDB_151531,IEDB_153197,IEDB_190606,IEDB_418918,IEDB_689191,IEDB_918314,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_40,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4518
Gebus C, Cottin C, Randriantsoa M, Drouillard S, Samain E "Synthesis of a-galactosyl epitopes by metabolically engineered Escherichia coli" -
Carbohydrate Research 361 (2012) 83-90
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
NCBI 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
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical methods, genetic methods
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Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (record IDs):
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