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Oldrini D, Del Bino L, Arda A, Carboni F, Henriques P, Angiolini F, Quintana JI, Calloni I, Romano MR, Berti F, Jiménez-Barbero J, Margarit I, Adamo R
Structure-Guided Design of a Group B Streptococcus Type III Synthetic Glycan-Conjugate Vaccine
Chemistry: a European Journal 26(31) (2020)
7018-7025
|
b-D-Galp-(1-4)-b-D-Glcp-(1-6)-+
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1--/(1->1)3-aminopropyl/ |
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Streptococcus sp. B III
(Ancestor NCBI TaxID 1319,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus [ICD11:
XN3NM 
]
NCBI PubMed ID: 32058627Publication DOI: 10.1002/chem.202000284Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: roberto.x.adamo
gsk.com
Institutions: Research Center, GlaxoSmithKline Plc, Via Fiorentina 1, 53100, Siena, Italy, Chemical Glycobiology Lab, CIC bioGUNE, Basque Research Technology Alliance (BRTA), Bizkaia Technology Park, 48160, Derio, Spain, Ikerbasque, Basque Foundation for Science, 48013, Bilbao, Bizkaia, Spain, Department Organic Chemistry II, University of the Basque Country UPV/EHU, 48940, Leioa, Bizkaia, Spain
Identification of glycan functional epitopes is of paramount importance for rational design of glycoconjugate vaccines. We recently mapped the structural epitope of the capsular polysaccharide from type III Group B Streptococcus (GBSIII), a major cause of invasive disease in newborns, by using a dimer fragment (composed of two pentasaccharide repeating units) obtained by depolymerization complexed with a protective mAb. Although reported data had suggested a highly complex epitope contained in a helical structure composed of more than four repeating units, we showed that such dimer conjugated to a carrier protein with a proper glycosylation degree elicited functional antibodies comparably to the full-length conjugated polysaccharide. Here, starting from the X-ray crystallographic structure of the polysaccharide fragment-mAb complex, we synthesized a hexasaccharide comprising exclusively the relevant positions involved in binding. Combining competitive surface plasmon resonance and saturation transfer difference NMR spectroscopy as well as in-silico modeling, we demonstrated that this synthetic glycan was recognized by the mAb similarly to the dimer. The hexasaccharide conjugated to CRM197, a mutant of diphtheria toxin, elicited a robust functional immune response that was not inferior to the polysaccharide conjugate, indicating that it may suffice as a vaccine antigen. This is the first evidence of an X-ray crystallography-guided design of a synthetic carbohydrate-based conjugate vaccine.
carbohydrates, Streptococcus, immunology, glycoconjugates, group B Streptococcus, vaccines, chemical synthesis, Humans, LAB, Structural glycobiology
Structure type: fragment of a bigger structure
Location inside paper: p.7020, Scheme 1, compound 10
Aglycon: (1->1)3-aminopropyl
Compound class: CPS
Contained glycoepitopes: IEDB_1083495,IEDB_130646,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149138,IEDB_149143,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
Methods: X-ray, ELISA, chemical synthesis, MD simulations, STD NMR, immunological assays, SPR, immunization, conjugation, STDNMR
Synthetic data: chemical
Related record ID(s): 5185, 32171
NCBI Taxonomy refs (TaxIDs): 1319Reference(s) to other database(s): GTC:G77068RO
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Oldrini D, Del Bino L, Arda A, Carboni F, Henriques P, Angiolini F, Quintana JI, Calloni I, Romano MR, Berti F, Jiménez-Barbero J, Margarit I, Adamo R
Structure-Guided Design of a Group B Streptococcus Type III Synthetic Glycan-Conjugate Vaccine
Chemistry: a European Journal 26(31) (2020)
7018-7025
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-+
|
b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-b-D-GlcpNAc-(1--/(1->1)3-aminopropyl/ |
Show graphically |
Streptococcus sp. B III
(Ancestor NCBI TaxID 1319,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus [ICD11:
XN3NM ]
The structure was elucidated in this paperNCBI PubMed ID: 32058627Publication DOI: 10.1002/chem.202000284Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: roberto.x.adamo
gsk.com
Institutions: Research Center, GlaxoSmithKline Plc, Via Fiorentina 1, 53100, Siena, Italy, Chemical Glycobiology Lab, CIC bioGUNE, Basque Research Technology Alliance (BRTA), Bizkaia Technology Park, 48160, Derio, Spain, Ikerbasque, Basque Foundation for Science, 48013, Bilbao, Bizkaia, Spain, Department Organic Chemistry II, University of the Basque Country UPV/EHU, 48940, Leioa, Bizkaia, Spain
Identification of glycan functional epitopes is of paramount importance for rational design of glycoconjugate vaccines. We recently mapped the structural epitope of the capsular polysaccharide from type III Group B Streptococcus (GBSIII), a major cause of invasive disease in newborns, by using a dimer fragment (composed of two pentasaccharide repeating units) obtained by depolymerization complexed with a protective mAb. Although reported data had suggested a highly complex epitope contained in a helical structure composed of more than four repeating units, we showed that such dimer conjugated to a carrier protein with a proper glycosylation degree elicited functional antibodies comparably to the full-length conjugated polysaccharide. Here, starting from the X-ray crystallographic structure of the polysaccharide fragment-mAb complex, we synthesized a hexasaccharide comprising exclusively the relevant positions involved in binding. Combining competitive surface plasmon resonance and saturation transfer difference NMR spectroscopy as well as in-silico modeling, we demonstrated that this synthetic glycan was recognized by the mAb similarly to the dimer. The hexasaccharide conjugated to CRM197, a mutant of diphtheria toxin, elicited a robust functional immune response that was not inferior to the polysaccharide conjugate, indicating that it may suffice as a vaccine antigen. This is the first evidence of an X-ray crystallography-guided design of a synthetic carbohydrate-based conjugate vaccine.
carbohydrates, Streptococcus, immunology, glycoconjugates, group B Streptococcus, vaccines, chemical synthesis, Humans, LAB, Structural glycobiology
Structure type: fragment of a bigger structure
Location inside paper: p.7020, Scheme 1, compound 1
Aglycon: (1->1)3-aminopropyl
Compound class: CPS
Contained glycoepitopes: IEDB_1083493,IEDB_1083495,IEDB_130646,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_1391966,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149138,IEDB_149143,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
Methods: X-ray, ELISA, chemical synthesis, MD simulations, STD NMR, immunological assays, SPR, immunization, conjugation, STDNMR
Biological activity: OPKA titers measured after the third immunization for hexasaccharide-CRM(197) glycoconjugate was 369.
Synthetic data: chemical
Related record ID(s): 5184, 32171
NCBI Taxonomy refs (TaxIDs): 1319Reference(s) to other database(s): GTC:G43676HY
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There is only one chemically distinct structure:
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Oldrini D, Del Bino L, Arda A, Carboni F, Henriques P, Angiolini F, Quintana JI, Calloni I, Romano MR, Berti F, Jiménez-Barbero J, Margarit I, Adamo R
Structure-Guided Design of a Group B Streptococcus Type III Synthetic Glycan-Conjugate Vaccine
Chemistry: a European Journal 26(31) (2020)
7018-7025
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-+
|
-4)-b-D-Glcp-(1-6)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1- |
Show graphically |
Streptococcus sp. B III
(Ancestor NCBI TaxID 1319,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus [ICD11:
XN3NM ]
NCBI PubMed ID: 32058627Publication DOI: 10.1002/chem.202000284Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: roberto.x.adamo
gsk.com
Institutions: Research Center, GlaxoSmithKline Plc, Via Fiorentina 1, 53100, Siena, Italy, Chemical Glycobiology Lab, CIC bioGUNE, Basque Research Technology Alliance (BRTA), Bizkaia Technology Park, 48160, Derio, Spain, Ikerbasque, Basque Foundation for Science, 48013, Bilbao, Bizkaia, Spain, Department Organic Chemistry II, University of the Basque Country UPV/EHU, 48940, Leioa, Bizkaia, Spain
Identification of glycan functional epitopes is of paramount importance for rational design of glycoconjugate vaccines. We recently mapped the structural epitope of the capsular polysaccharide from type III Group B Streptococcus (GBSIII), a major cause of invasive disease in newborns, by using a dimer fragment (composed of two pentasaccharide repeating units) obtained by depolymerization complexed with a protective mAb. Although reported data had suggested a highly complex epitope contained in a helical structure composed of more than four repeating units, we showed that such dimer conjugated to a carrier protein with a proper glycosylation degree elicited functional antibodies comparably to the full-length conjugated polysaccharide. Here, starting from the X-ray crystallographic structure of the polysaccharide fragment-mAb complex, we synthesized a hexasaccharide comprising exclusively the relevant positions involved in binding. Combining competitive surface plasmon resonance and saturation transfer difference NMR spectroscopy as well as in-silico modeling, we demonstrated that this synthetic glycan was recognized by the mAb similarly to the dimer. The hexasaccharide conjugated to CRM197, a mutant of diphtheria toxin, elicited a robust functional immune response that was not inferior to the polysaccharide conjugate, indicating that it may suffice as a vaccine antigen. This is the first evidence of an X-ray crystallography-guided design of a synthetic carbohydrate-based conjugate vaccine.
carbohydrates, Streptococcus, immunology, glycoconjugates, group B Streptococcus, vaccines, chemical synthesis, Humans, LAB, Structural glycobiology
Structure type: polymer chemical repeating unit
Location inside paper: p.7020, Fig. 1
Trivial name: PS-III
Compound class: CPS, EPS, polysaccharide
Contained glycoepitopes: IEDB_1083493,IEDB_1083495,IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_1392542,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142344,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_143634,IEDB_146100,IEDB_146107,IEDB_146664,IEDB_149138,IEDB_149139,IEDB_149141,IEDB_149142,IEDB_149143,IEDB_149144,IEDB_149145,IEDB_149147,IEDB_149148,IEDB_149150,IEDB_149151,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_161524,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
Methods: X-ray, ELISA, chemical synthesis, MD simulations, STD NMR, immunological assays, SPR, immunization, conjugation, STDNMR
Comments, role: Streptococcus sp. group B type III; published polymerization frame was shifted for conformity with other records.
Related record ID(s): 5184, 5185
NCBI Taxonomy refs (TaxIDs): 1319Reference(s) to other database(s): GTC:G35073UM, GlycomeDB:
11408, CCSD:
43274, CBank-STR:17387
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There is only one chemically distinct structure:
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