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1. (CSDB ID: 23631) | report error |
| a-Colp-(1-4)-+ | P-6:4)-+ | | | a-Colp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-D-GalpA-(1-3)-b-D-QuipNAc-(1-?)-Subst Subst = O-antigen | Show graphically |
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Vibrio cholerae O139
(NCBI TaxID 45888,
species name lookup)
, ICD11: SA55 ]; hypotension [ICD11: BA2Y , ICD11: BA2Z ]
helix.nih.govThe fragments described contain a galactose residue with cyclic 4,6-phosphate and are equipped with an amino-functionalized spacer, allowing further derivatization or direct conjugation to suitable carriers. The core Gal-(1-3)-GlcNAc disaccharide was obtained by condensation of 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside with 2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl bromide under Helferich conditions. Reductive opening of the benzylidene acetal, followed by deacetylation and selective benzylation gave 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-b-D-galactopyranosyl)-2-deoxy-b-D-glucopyranoside, which was regioselectively phosphorylated to give two isomeric 4,6-cyclic 2,2,2-trichloroethyl phosphates. The (R) phosphate was subjected to catalytic hydrogenation/hydrogenolysis to give the fully deprotected title disaccharide fragment. Glycosylation of the (S)-phosphate diol with 2,4-di-O-benzyl-3,6-dideoxy-a-L-xylo-hexopyranosyl bromide under halide-asisted conditions yielded a mixture of the tetrasaccharide and a trisaccharide, which were readily separable by chromatography. Their hydrogenation/hydrogenolysis effected global deprotection as well as reduction of the azide, to furnish the deprotected.
carbohydrates, Oligosaccharides, glycosylation, conjugate vaccine, regioselective phosphorylation
Structure type: oligomer|
2. (CSDB ID: 23940) | report error |
| P-6:4)-+ | a-Colp-(1-2)-b-D-Galp-(1--/spacer-squaric acid/ | Show graphically |
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Vibrio cholerae O139
(NCBI TaxID 45888,
species name lookup)
, ICD11: SA55 ]; hypotension [ICD11: BA2Y , ICD11: BA2Z ]helix.nih.govThe fragments described contain a galactose residue with cyclic 4,6-phosphate and are equipped with an amino-functionalized spacer, allowing further derivatization or direct conjugation to suitable carriers. The core Gal-(1-3)-GlcNAc disaccharide was obtained by condensation of 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside with 2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl bromide under Helferich conditions. Reductive opening of the benzylidene acetal, followed by deacetylation and selective benzylation gave 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-b-D-galactopyranosyl)-2-deoxy-b-D-glucopyranoside, which was regioselectively phosphorylated to give two isomeric 4,6-cyclic 2,2,2-trichloroethyl phosphates. The (R) phosphate was subjected to catalytic hydrogenation/hydrogenolysis to give the fully deprotected title disaccharide fragment. Glycosylation of the (S)-phosphate diol with 2,4-di-O-benzyl-3,6-dideoxy-a-L-xylo-hexopyranosyl bromide under halide-asisted conditions yielded a mixture of the tetrasaccharide and a trisaccharide, which were readily separable by chromatography. Their hydrogenation/hydrogenolysis effected global deprotection as well as reduction of the azide, to furnish the deprotected.
carbohydrates, Oligosaccharides, glycosylation, conjugate vaccine, regioselective phosphorylation
Structure type: oligomer|
3. (CSDB ID: 23941) | report error |
| a-Colp-(1-4)-+ | P-6:4)-+ | | | a-Colp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1--/8-amino-3,6-dioxaoctyl/ | Show graphically |
|
Show legend Show as text |
Vibrio cholerae O139
(NCBI TaxID 45888,
species name lookup)
, ICD11: SA55 ]; hypotension [ICD11: BA2Y , ICD11: BA2Z ]helix.nih.govThe fragments described contain a galactose residue with cyclic 4,6-phosphate and are equipped with an amino-functionalized spacer, allowing further derivatization or direct conjugation to suitable carriers. The core Gal-(1-3)-GlcNAc disaccharide was obtained by condensation of 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside with 2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl bromide under Helferich conditions. Reductive opening of the benzylidene acetal, followed by deacetylation and selective benzylation gave 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-b-D-galactopyranosyl)-2-deoxy-b-D-glucopyranoside, which was regioselectively phosphorylated to give two isomeric 4,6-cyclic 2,2,2-trichloroethyl phosphates. The (R) phosphate was subjected to catalytic hydrogenation/hydrogenolysis to give the fully deprotected title disaccharide fragment. Glycosylation of the (S)-phosphate diol with 2,4-di-O-benzyl-3,6-dideoxy-a-L-xylo-hexopyranosyl bromide under halide-asisted conditions yielded a mixture of the tetrasaccharide and a trisaccharide, which were readily separable by chromatography. Their hydrogenation/hydrogenolysis effected global deprotection as well as reduction of the azide, to furnish the deprotected.
carbohydrates, Oligosaccharides, glycosylation, conjugate vaccine, regioselective phosphorylation
Structure type: oligomer|
4. (CSDB ID: 23942) | report error |
| P-6:4)-+ | a-Colp-(1-2)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1--/8-amino-3,6-dioxaoctyl/ | Show graphically |
|
Show legend Show as text |
Vibrio cholerae O139
(NCBI TaxID 45888,
species name lookup)
, ICD11: SA55 ]; hypotension [ICD11: BA2Y , ICD11: BA2Z ]helix.nih.govThe fragments described contain a galactose residue with cyclic 4,6-phosphate and are equipped with an amino-functionalized spacer, allowing further derivatization or direct conjugation to suitable carriers. The core Gal-(1-3)-GlcNAc disaccharide was obtained by condensation of 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside with 2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl bromide under Helferich conditions. Reductive opening of the benzylidene acetal, followed by deacetylation and selective benzylation gave 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-b-D-galactopyranosyl)-2-deoxy-b-D-glucopyranoside, which was regioselectively phosphorylated to give two isomeric 4,6-cyclic 2,2,2-trichloroethyl phosphates. The (R) phosphate was subjected to catalytic hydrogenation/hydrogenolysis to give the fully deprotected title disaccharide fragment. Glycosylation of the (S)-phosphate diol with 2,4-di-O-benzyl-3,6-dideoxy-a-L-xylo-hexopyranosyl bromide under halide-asisted conditions yielded a mixture of the tetrasaccharide and a trisaccharide, which were readily separable by chromatography. Their hydrogenation/hydrogenolysis effected global deprotection as well as reduction of the azide, to furnish the deprotected.
carbohydrates, Oligosaccharides, glycosylation, conjugate vaccine, regioselective phosphorylation
Structure type: oligomer| New query | Export IDs | Home | Help |
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