Found 34 structures.
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1. Compound ID: 47
Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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2. Compound ID: 66
Structure type: oligomer
Contained glycoepitopes: IEDB_114701,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_167188,IEDB_174332,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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3. Compound ID: 67
Structure type: oligomer
Contained glycoepitopes: IEDB_114701,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_167188,IEDB_174332,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 17
Blixt O, Van Die I, Norberg T, van den Eijnden DH "High-level expression of the Neisseria meningitidis lgtA gene in Escherichia coli and characterization of the encoded N-acetylglucosaminyltransferase as a useful catalyst in the synthesis of GlcNAcb1→3Gal and GalNAcb1-3Gal linkages" -
Glycobiology 9(10) (1999) 1061-1071
We have expressed the Neisseria meningitidis lgtA gene at a high level in Escherichia coli. The encoded β-N-acetylglucosaminyltransferase, referred to as LgtA, which in the bacterium is involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosaccharide, was obtained in an enzymatically highly active form. This glycosyltransferase appeared to be unusual in that it displays a broad acceptor specificity toward both α- and β-galactosides, whether structurally related to N- or O-protein-, or lipid-linked oligosaccharides. Product analysis by one- and two-dimensional 400 MHz 1H- and 13C NMR spectroscopy reveals that LgtA catalyzes the introduction of GlcNAc from UDP-GlcNAc in a β1→3-linkage to accepting Gal residues. The enzyme can thus be characterized as a UDP-GlcNAc:Gal α/β-R β 3-N-acetylglucosaminyltransferase. Although lactose is a highly preferred acceptor substrate the recombinant enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine revealing its potential value in the synthesis of polylactosaminoglycan structures in enzyme assisted procedures. Furthermore, LgtA shows a high donor promiscuity toward UDP-GalNAc, but not toward other UDP-sugars, and can catalyze the introduction of GalNAc in β1→3-linkage to α- or β-Gal in the acceptor structures at moderate rates. LgtA therefore shows promise to be a useful catalyst in the preparative synthesis of both GlcNAc β1→3 Gal and GalNAc β1→3 Gal linkages.
oligosaccharide, enzyme-assisted-synthesis, recombinant glycosyltransferase, glycosidic linkage, polylactosaminoglycan, recombinant glycosyltrasferase
NCBI PubMed ID: 10521543Publication DOI: 10.1093/glycob/9.10.1061Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Medical Chemistry, Vrije Universiteit, Van der Boechorstraat 7, 1081 BT Amsterdam, The Netherlands
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, enzyme-assisted synthesis, DNA techniques, glycosyltransferase assays, kinetics assays
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4. Compound ID: 1778
|
b-D-GlcpNAc-(1-3)-+
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-7)-Bn |
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Structure type: oligomer
Trivial name: repeating unit of the O-polysaccharide
Contained glycoepitopes: IEDB_131174,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_144825,IEDB_151531,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 556
Barone G, Bedini E, Unverzagt C, Parilli M "Synthesis of the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010" -
Carbohydrate Research 339(2) (2004) 393-400
The synthesis of the repeating unit of the major O-antigen component from Pseudomonas syringae pv. ribicola NVPPB 1010 is reported. The strategy used was based on the successive coupling of a trisaccharide rhamnosyl trichloroacetimidate with a rhamnosyl acceptor with a free hydroxyl group on C-2. The pentasaccharide was then obtained by coupling with a N-Troc-tri-O-acetyl-glucosamine trichloroacetimidate. The synthesis allowed the oligomerisation of the repeating unit.
repeating unit, Oligosaccharides, O-chain, glycosylation, Pseudomonas ribicola
NCBI PubMed ID: 14698898Publication DOI: 10.1016/j.carres.2003.10.002Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: parrilli@unina.it
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli ''Federico II'', Complesso Universitario Monte Santangelo, Via Cintia 4, 80126 Napoli, Italy, Bioorganische Chemie, Gebaude NWI, Universitat Bayreuth,95440 Bayreuth, Germany
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5. Compound ID: 4053
Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1496
Bedini E, De Castro C, Erbs G, Mangoni L, Dow JM, Newman MA, Parrilli M, Unverzagt C "Structure-dependent modulation of a pathogen response in plants by synthetic O-antigen polysaccharides" -
Journal of the American Chemical Society 127(8) (2005) 2414-2416
Many phytopathogenic bacteria display lipopolysaccharides (LPS) with the O-chain repeating unit [α-L-Rha-(1→3)-α-L-Rha-(1→3)-α-L-Rha-(1→2)](n). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP)
Lipopolysaccharide, structure, O-antigen, molecular dynamics, NMR spectroscopy, conformational analysis, Pseudomonas syringae, gene expression, rhamnan, Arabidopsis
NCBI PubMed ID: 15724995Journal NLM ID: 7503056Publisher: American Chemical Society
Institutions: Dipartimento di Chimica Organica e Biochimica Complesso, Universitario Monte Sant'Angelo, Via Cintia 4, 80126, Napoli, Italy, Section for Plant Pathology, Royal Veterinary and Agricultural University, Thorvaldsensvej 40, 1871 Frederiksberg, Denmark, BIOMERIT Research Centre, Department of Microbiology, BioSciences Institute, National University of Ireland, Cork, Ireland, Bioorganische Chemie, Gebäude NWI, Universität Bayreuth, D-95440 Bayreuth, Germany
Methods: NMR-2D, NMR, chemical synthesis, biological assays, MD simulations
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6. Compound ID: 4054
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rha-(1-7)-Bn |
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Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1496
Bedini E, De Castro C, Erbs G, Mangoni L, Dow JM, Newman MA, Parrilli M, Unverzagt C "Structure-dependent modulation of a pathogen response in plants by synthetic O-antigen polysaccharides" -
Journal of the American Chemical Society 127(8) (2005) 2414-2416
Many phytopathogenic bacteria display lipopolysaccharides (LPS) with the O-chain repeating unit [α-L-Rha-(1→3)-α-L-Rha-(1→3)-α-L-Rha-(1→2)](n). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP)
Lipopolysaccharide, structure, O-antigen, molecular dynamics, NMR spectroscopy, conformational analysis, Pseudomonas syringae, gene expression, rhamnan, Arabidopsis
NCBI PubMed ID: 15724995Journal NLM ID: 7503056Publisher: American Chemical Society
Institutions: Dipartimento di Chimica Organica e Biochimica Complesso, Universitario Monte Sant'Angelo, Via Cintia 4, 80126, Napoli, Italy, Section for Plant Pathology, Royal Veterinary and Agricultural University, Thorvaldsensvej 40, 1871 Frederiksberg, Denmark, BIOMERIT Research Centre, Department of Microbiology, BioSciences Institute, National University of Ireland, Cork, Ireland, Bioorganische Chemie, Gebäude NWI, Universität Bayreuth, D-95440 Bayreuth, Germany
Methods: NMR-2D, NMR, chemical synthesis, biological assays, MD simulations
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7. Compound ID: 4055
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rha-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rha-(1-7)-Bn |
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Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_2116141,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1496
Bedini E, De Castro C, Erbs G, Mangoni L, Dow JM, Newman MA, Parrilli M, Unverzagt C "Structure-dependent modulation of a pathogen response in plants by synthetic O-antigen polysaccharides" -
Journal of the American Chemical Society 127(8) (2005) 2414-2416
Many phytopathogenic bacteria display lipopolysaccharides (LPS) with the O-chain repeating unit [α-L-Rha-(1→3)-α-L-Rha-(1→3)-α-L-Rha-(1→2)](n). This trisaccharide unit was synthesized and oligomerized to obtain hexa- and nonasaccharides. The deprotected rhamnans were effective in suppressing the hypersensitive response (HR) and in inducing PR-1 gene expression in Arabidopsis thaliana. Conformational analysis of the oligorhamnans by NMR spectroscopy and molecular dynamics calculations revealed that a coiled structure develops with increasing chain length of the oligosaccharide. This is associated with increasing efficacy in HR suppression and PR-1 gene expression. We therefore infer that the coiled structure of phytopathogenic bacteria is a plant-recognizable pathogen-associated molecular pattern (PAMP)
Lipopolysaccharide, structure, O-antigen, molecular dynamics, NMR spectroscopy, conformational analysis, Pseudomonas syringae, gene expression, rhamnan, Arabidopsis
NCBI PubMed ID: 15724995Journal NLM ID: 7503056Publisher: American Chemical Society
Institutions: Dipartimento di Chimica Organica e Biochimica Complesso, Universitario Monte Sant'Angelo, Via Cintia 4, 80126, Napoli, Italy, Section for Plant Pathology, Royal Veterinary and Agricultural University, Thorvaldsensvej 40, 1871 Frederiksberg, Denmark, BIOMERIT Research Centre, Department of Microbiology, BioSciences Institute, National University of Ireland, Cork, Ireland, Bioorganische Chemie, Gebäude NWI, Universität Bayreuth, D-95440 Bayreuth, Germany
Methods: NMR-2D, NMR, chemical synthesis, biological assays, MD simulations
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8. Compound ID: 6879
|
a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-7)-Bn |
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Structure type: oligomer
Trivial name: rhamnan oligosaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 3148
De Castro C, Carannante A, Lanzetta R, Liparoti V, Molinaro A, Parrilli M "Core oligosaccharide structure from the highly phytopathogenic A. tumefaciens TT111 and conformational analysis of the putative rhamnan epitope" -
Glycobiology 341(18) (2006) 2954-2958
The structure of the complex mixture of the core oligosaccharide components of the lipooligosaccharide fraction of Agrobacterium tumefaciens strain TT111 was determined directly on the deacetylated products, by means of spectroscopical methods. The Rhamnan oligosaccharide elongating the inner Kdo residue shares structural features with other polysaccharide from well-known plant pathogenic bacteria. Its conformation was determined thorough extensive Molecular Dynamic analysis and anneals forming an epitope similar to that recognised from the plant defence system
Lipooligosaccharide, NMR spectroscopy, structure elucidation, conformational analysis, Agrobacterium tumefaciens
NCBI PubMed ID: 16877750Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: decastro@unina.it
Institutions: Department of Organic Chemistry and Biochemistry, University of Naples, Complesso Universitario Monte Sant' Angelo, Via Cintia 4, 80126 Napoli, Italy
Methods: methylation, NMR, SDS-PAGE, alkaline degradation, MALDI-MS, composition analysis
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9. Compound ID: 15075
|
b-D-Galf-(1-2)-b-D-Galf-(1-4)-+
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b-D-Galp-(1-2)-+ |
| |
a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-Galp-(1-6)-a-D-GlcpNAc-(1-7)-Bn |
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Structure type: oligomer
; 1435.4856 [M+Na]+
Trivial name: mucin oligosaccharide
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_146100,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_241097,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 5883
Agustí R, Giorgi ME, Mendoza VM, Kashiwagi GA, de Lederkremer RM, Gallo-Rodriguez C "Synthesis of the O-linked hexasaccharide containing β-D-Galp-(1→2)-D-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides" -
Organic and Biomolecular Chemistry 23(6) (2015) 1213-1222
The hexasaccharide β-D-Galp-(1→2)-[β-D-Galp-(1→3)]-β-D-Galp-(1→6)-[β-D-Galp(1→2)-β-D-Galf(1→4)]-D-GlcNAc (10) and its β-D-Galf-(1→2)-β-D-Galf containing isomer (7) are the largest carbohydrates in mucins of some strains of Trypanosoma cruzi. The terminal β-D-Galp units are sites of sialylation by the parasite trans-sialidase. Hexasaccharide 10 was chemically synthesized for the first time by a [3+3] nitrilium based convergent approach, using the trichloroacetimidate method of glycosylation. The (1)H NMR spectrum of its alditol was identical to the spectrum of the product released by β-elimination from the parasite mucin. The trans-sialylation reaction studied on the benzyl glycoside of 10 showed two monosialylated products whose relative abundance changed with time. On the other hand, only one product was produced by sialylation of the benzyl glycoside of 7. A preparative synthesis of the latter and spectroscopic analysis of the product unequivocally established the sialylation site at the less hindered (1→3)-linked galactopyranose.
Oligosaccharides, galactofuranose, glycosylation, Trypanosoma cruzi, mucins, Nitrilium, Parasite, trans-sialidase
NCBI PubMed ID: 25703305Publication DOI: 10.1016/j.bmc.2015.01.056Journal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: R.M. de Lederkremer
; C. Gallo-Rodriguez
Institutions: CIHIDECAR, Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Methods: 13C NMR, 1H NMR, TLC, HPAEC, chemical synthesis, HPAEC-PAD, sialylation, ESI-TOF-MS
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10. Compound ID: 15076
|
b-D-Galp-(1-2)-b-D-Galf-(1-4)-+
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b-D-Galp-(1-2)-+ |
| |
a-Neup5Ac-(2-3)-b-D-Galp-(1-3)-b-D-Galp-(1-6)-a-D-GlcpNAc-(1-7)-Bn |
Show graphically |
Structure type: oligomer
Trivial name: mucin oligosaccharide
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_146100,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_241097,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 5883
Agustí R, Giorgi ME, Mendoza VM, Kashiwagi GA, de Lederkremer RM, Gallo-Rodriguez C "Synthesis of the O-linked hexasaccharide containing β-D-Galp-(1→2)-D-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides" -
Organic and Biomolecular Chemistry 23(6) (2015) 1213-1222
The hexasaccharide β-D-Galp-(1→2)-[β-D-Galp-(1→3)]-β-D-Galp-(1→6)-[β-D-Galp(1→2)-β-D-Galf(1→4)]-D-GlcNAc (10) and its β-D-Galf-(1→2)-β-D-Galf containing isomer (7) are the largest carbohydrates in mucins of some strains of Trypanosoma cruzi. The terminal β-D-Galp units are sites of sialylation by the parasite trans-sialidase. Hexasaccharide 10 was chemically synthesized for the first time by a [3+3] nitrilium based convergent approach, using the trichloroacetimidate method of glycosylation. The (1)H NMR spectrum of its alditol was identical to the spectrum of the product released by β-elimination from the parasite mucin. The trans-sialylation reaction studied on the benzyl glycoside of 10 showed two monosialylated products whose relative abundance changed with time. On the other hand, only one product was produced by sialylation of the benzyl glycoside of 7. A preparative synthesis of the latter and spectroscopic analysis of the product unequivocally established the sialylation site at the less hindered (1→3)-linked galactopyranose.
Oligosaccharides, galactofuranose, glycosylation, Trypanosoma cruzi, mucins, Nitrilium, Parasite, trans-sialidase
NCBI PubMed ID: 25703305Publication DOI: 10.1016/j.bmc.2015.01.056Journal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: R.M. de Lederkremer
; C. Gallo-Rodriguez
Institutions: CIHIDECAR, Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Methods: 13C NMR, 1H NMR, TLC, HPAEC, chemical synthesis, HPAEC-PAD, sialylation, ESI-TOF-MS
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11. Compound ID: 15077
|
b-D-Galp-(1-3)-+
|
b-D-Galp-(1-2)-b-D-Galp-(1-6)-+
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-2)-b-D-Galf-(1-4)-a-D-GlcpNAc-(1-7)-Bn |
Show graphically |
Structure type: oligomer
Trivial name: mucin oligosaccharide
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_146100,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_241097,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 5883
Agustí R, Giorgi ME, Mendoza VM, Kashiwagi GA, de Lederkremer RM, Gallo-Rodriguez C "Synthesis of the O-linked hexasaccharide containing β-D-Galp-(1→2)-D-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides" -
Organic and Biomolecular Chemistry 23(6) (2015) 1213-1222
The hexasaccharide β-D-Galp-(1→2)-[β-D-Galp-(1→3)]-β-D-Galp-(1→6)-[β-D-Galp(1→2)-β-D-Galf(1→4)]-D-GlcNAc (10) and its β-D-Galf-(1→2)-β-D-Galf containing isomer (7) are the largest carbohydrates in mucins of some strains of Trypanosoma cruzi. The terminal β-D-Galp units are sites of sialylation by the parasite trans-sialidase. Hexasaccharide 10 was chemically synthesized for the first time by a [3+3] nitrilium based convergent approach, using the trichloroacetimidate method of glycosylation. The (1)H NMR spectrum of its alditol was identical to the spectrum of the product released by β-elimination from the parasite mucin. The trans-sialylation reaction studied on the benzyl glycoside of 10 showed two monosialylated products whose relative abundance changed with time. On the other hand, only one product was produced by sialylation of the benzyl glycoside of 7. A preparative synthesis of the latter and spectroscopic analysis of the product unequivocally established the sialylation site at the less hindered (1→3)-linked galactopyranose.
Oligosaccharides, galactofuranose, glycosylation, Trypanosoma cruzi, mucins, Nitrilium, Parasite, trans-sialidase
NCBI PubMed ID: 25703305Publication DOI: 10.1016/j.bmc.2015.01.056Journal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: R.M. de Lederkremer
; C. Gallo-Rodriguez
Institutions: CIHIDECAR, Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Methods: 13C NMR, 1H NMR, TLC, HPAEC, chemical synthesis, HPAEC-PAD, sialylation, ESI-TOF-MS
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12. Compound ID: 19462
Structure type: oligomer
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_190606,IEDB_885812
The structure is contained in the following publication(s):
- Article ID: 5306
Marino C, Rinflerch A, de Lederkremer RM "Galactofuranose antigens, a target for diagnosis of fungal infections in humans" -
Future Science OA 3(3) (2017) FSO199
The use of biomarkers for the detection of fungal infections is of interest to complement histopathological and culture methods. Since the production of antibodies in immunocompromised patients is scarce, detection of a specific antigen could be effective for early diagnosis. D-Galactofuranose (Galf) is the antigenic epitope in glycoconjugates of several pathogenic fungi. Since Galf is not biosynthesized by mammals, it is an attractive candidate for diagnosis of infection. A monoclonal antibody that recognizes Galf is commercialized for detection of aspergillosis. The linkage of Galf in the natural glycans and the chemical structures of the synthesized Galf-containing oligosaccharides are described in this paper. The oligosaccharides could be used for the synthesis of artificial carbohydrate-based antigens, not enough exploited for diagnosis.
galactofuranose, immune response, diagnosis, biomarkers, fungal infections, synthetic haptens
NCBI PubMed ID: 28883999Publication DOI: 10.4155/fsoa-2017-0030Journal NLM ID: 101665030Publisher: London: Future Science Group
Correspondence: Marino C
; de Lederkremer RM
Institutions: Universidad de Buenos Aires, Consejo Nacional de Investigaciones Científicas y Técnicas, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellón II, Ciudad Universitaria, Buenos Aires, Argentina, Servicio de Dermatología, Dermatología Experimental, Hospital Italiano de Buenos Aires, Buenos Aires, Argentina
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13. Compound ID: 21645
Structure type: monomer
; 254.115423
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 8728
Kadhim MJ, Mohammed GJ, Hussein HM "Analysis of bioactive metabolites from Candida albicans using (GCMS) and evaluation of antibacterial activity" -
International Journal of Pharmaceutical and Clinical Research 8(7) (2016) 655-670
The objectives of this research were analysis of the secondary metabolite produced by Candida albicans and evaluation antibacterial activity. Bioactives are chemical compounds often referred to as secondary metabolites. Thirty nine bioactive compounds were identified in the methanolic extract of Candida albicans. The identification of bioactive chemical compounds is based on the peak area, retention time molecular weight and molecular formula. GC-MS analysis of Candida albicans revealed the existence of the 1,4-Benzendiol, 2,6-bis (1,1-dimethylethyl)-, Thieno[2,3-c]furan-3-carboniterile, 2-amino-4,6-dihydro-4,4,6,6-te, Z-8-Methyl-9-tetradecenoic acid, i-Propyl 9-tetradecenoate, 9,12,15,-Octadecatrienoic, 2-[(trimethylsilyl)oxy]-1-[(trimethyl, 17-Octadecynoic acid, Oxime-, methoxy-phenyl-, Edulanll, p-Menth-1-en-3-one, semicarbazone, 5,7-dodecadiyn-1,12-diol, Methyl 2-O-benzyl-d-arabinofuranoside, Erythritol, d-Glycero-l-gluco-heptose, D-Glucose, 6-O-α-D-galactopyranosyl-, l-Gala-l-ido-octonic lactone, Desulphosingrin, 2(3H)-Furanone, 3-butyldihydro-, β-Hydroxyquebrachamine, 1,4-benzendiol, 2,6-bis(1,1-dimethylethyl)-, 9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triol,(3β,5Z,7E)-,N-(4,6-Dimethyl-2-pyrimi-dinyl)-4-(4-nitrobenzylideneamino)benzel, 2,7-Diphenyl-1,6-dioxopyridazino [4,5:2’,3’] pyrrolo[4’,5’-d]pyridazin, 2-Methyl-9-β-D-ribofuranosylhypoxanthine, Ergosta-5, 22-dien-3-ol,acetate,(3β,22E)-, 10-Heptadecen-8-ynoic acid, methyl ester, (E)-, Chromone, 5-hydroxy-6,7,8-trimethoxy-2,3-dimethyl-, 1-Methyl-8-propyl-3,6-diazahomoadamantan-9-ol, 1-(4-Amino-furazan-3-yl)-5-dimethylaminomethyl-1H-[1,2,3]triazole, 5-Bromo-8-[(4-hydroxybenzylidene) amino]quinolone, Carbamic acid, N-methyl-,(6-chloro-2-methyl-1,1-dioxidobenzo), d-Mannose, α-D-Glucopyranoside, O-α-D-glucopyranosyl-(1.fwdarw.3)-β-D-, 12-Methyl-oxa-cyclododecan-2-one, Acetamide, N-methyl-N-[4-[2acetoxymethyl-1-pyrrolidyl]-2-butyn, Acetamide, N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2butynyl]-, Estra-1,3,5(10)-triene-17β-ol, Curan-17-oic acid, 19,20-dihydroxy-,methyl ester,(19S)-, 2,5,5,8A-Tetramethyl-6,7,8,8atetrahydro-5H-chromen-8-ol and 6-Octadecenoic acid. Proteus mirabilis was very highly antifungal activity (6.19±0.20) mm while Neriumolender (Alkaloids) has maximum zone formation (7.67±0.21) mm against Aspergillus fumigatus.
Candida albicans, antibacterial activity, GC-MS, antifungal activity, secondary metabolites, FT-IR
WWW link: https://www.researchgate.net/publication/306314562_Analysis_of_bioactive_metabolites_from_Candida_albicans_using_GC-MS_and_evaluation_of_antibacterial_activityInstitutions: Department of Genetic Engineering, Al-Qasim Green University, Iraq, College of Science, Al-Qadisyia University, Iraq
Methods: GC-MS, antibacterial assay, antifungal activity test, FT-IR
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14. Compound ID: 22276
Structure type: monomer
; 255.1185 [M+H]+
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9101
Dewi RT, Ekapratiwi Y, Sundowo A, Ariani N, Yolanda T, Filaila E "Bioconversion of quercetin glucosides from Dendrophthoe pentandra leaf using Aspergillus acueletus LS04-3" -
AIP Conference Proceedings 2175(1) (2019) ID 020048
Mistletoe (Dendrophthoe pentandra Miq.) leaves serve as a herbal medicine, particularly used in Indonesian folk medicine, for treating various immunological disorders and cancers. One major active compound of mistletoe plant was flavonoid that occured in the form of glycosides (quercetin-3-O-rhamnoside) instead of aglycone (quercetin). Quercetin from the flavonoid group had high bioactivities than that in glycosidic form. The fermentation of flavonoid glycoside with filamentous fungi resulted in the conversion of bioactive compounds. The objectives of this study were to explore the derivatives of quercetin-3-O-rhamnoside during fungal fermentation of water-extracted mistletoe (D. pentandra Miq.) leaves (B) by A. acueletus LS04-3 and investigate the influence of glucose (B+G), yeast (B+Y), and both glucose and yeast (B+G+Y) in the medium on the metabolism of quercetin-3-O-rhamnosidebased on HPLC and LCMS-MS analysis. Based on HPLC analysis, the addition of yeast to the medium (B+Y) increased the conversion of glucoside to quercetin almost twice as much as that on the control medium (B), during the first day of incubation period (D-1). The 10% increase of quercetin peak was only seen on the third day of incubation in B+G medium, when compared to the control sample (B). Moreover, LCMS-MS analysis revealed that quercetin-3-O-rhamnoside and quercetin were detected as the major components in fermented mistletoe leaves. Furthermore, quercetin-3-galactoside-7-glucoside and robinetin were found in the medium that had been added with glucose. The study suggest that glycosilation could also occur in processes other than hydrolisis of glycoside because external glucose would affect the energy metabolism and sugar activation of the microbe. Our finding expanded the understanding of the mistletoe leaf fermentation process and provided further guidance for the biotransformation of quercetin-3-O-rhamnoside in scale up production.
quercetin, bioconversion, quercetin-3-O-rhamnoside, Aspergillus acueletus
Publication DOI: 10.1063/1.5134612Journal NLM ID: 101515450Publisher: New York: American Institute of Physics
Correspondence: Dewi RT
Institutions: Research Center for Chemistry LIPI, Kawasan PUSPIPTEK, Serpong, Indonesia
Methods: HPLC, biosynthetic methods, extraction, cell growth, LC-MS/MS, evaporation
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15. Compound ID: 22304
Structure type: oligomer
; 425.1341 [M+Na]+
C18H26O10
Trivial name: icariside F2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9147
Eldin AM, Kamel Z, Hossam N "Purification and identification of surface active amphiphilic candidates produced by Geotrichum candidum MK880487 possessing antifungal property" -
Journal of Dispersion Science and Technology 2020 (2020) ID 1813157
The present study was held to optimize production, purify and identify biosurfactant from yeast strain Geotrichum candidum MK880487. Biosurfactant production was done on modified Hua medium and optimized in shake-flask method. Soybean oil (8%, v/v), KNO3 (0.75 g/L) and yeast extract (0.3 g/L) were the best carbon and nitrogen sources, respectively, with C:N ratio of 200:1, pH 8 at 30 °C for 168 h. Production scale-up was achieved on 2.5 L bioreactor as batch method. The resulting crude biosurfactant extract with yield of 1.75 g/L was purified by reversed phase column preparative HPLC. The resulting most active fraction F47 significantly reduced water surface tension by 51.92%. Chemical characterization using TLC, GC-MS, FTIR and LC-MS/MS methods revealed the biosurfactant to contain mainly glycolipid structure existing as mixture of Icariside F2, Cardenolide Di-Hexopyranoside and Di Galactosyl Di Acyl Glycerol glycolipid that collectively showed potential antifungal activity toward Macrophomina phaseolina.
biosurfactant, LC-MS/MS, biocontrol, Geotrichum candidum
Publication DOI: 10.1080/01932691.2020.1813157Journal NLM ID: 9878574Publisher: New York, M. Dekker
Correspondence: Eldin AM
Institutions: Department of Soil Microbiology, Soils, Waters and Environmental Research Institute, Agricultural Research Center, Giza, Egypt, Department of Microbiology, Faculty of Science, Cairo University, Giza, Egypt
Methods: IR, GC-MS, TLC, HPLC, viscosity measurement, extraction, LC-ESI-MS, cell growth, evaporation, centrifugation, antifungal activity test
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