Found 4 structures.
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1. Compound ID: 1845
|
b-D-Glcp-(1-6)-+
|
a-Neup5Ac9Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-D-Gal |
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Structure type: oligomer
Trivial name: CPS repeating unit
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136095,IEDB_136794,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142344,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149139,IEDB_149142,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_241113,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 582
Lewis AL, Nizet V, Varki A "Discovery and characterization of sialic acid O-acetylation in group B Streptococcus" -
Proceedings of the National Academy of Sciences of the USA 101(30) (2004) 11123-11128
Group B Streptococcus (GBS) is the leading cause of human neonatal sepsis and meningitis. The GBS capsular polysaccharide is a major virulence factor and the active principle of vaccines in phase II trials. All GBS capsules have a terminal α 2-3-linked sialic acid [N-acetylneuraminic acid (Neu5Ac)], which interferes with complement-mediated killing. We show here that some of the Neu5Ac residues of the GBS type III capsule are O-acetylated at carbon position 7, 8, or 9, a major modification evidently missed in previous studies. Data are consistent with initial O-acetylation at position 7, and subsequent migration of the O-acetyl ester at positions 8 and 9. O-acetylation was also present on several other GBS serotypes (Ia, Ib, II, V, and VI). Deletion of the CMP-Neu5Ac synthase gene neuA by precise, in-frame allelic replacement gave intracellular accumulation of O-acetylated Neu5Ac, whereas overexpression markedly decreased O-acetylation. Given the known GBS Neu5Ac biosynthesis pathway, these data indicate that O-acetylation occurs on free Neu5Ac, competing with the CMP-Neu5Ac synthase. O-acetylation often generates immunogenic epitopes on bacterial capsular polysaccharides and can modulate human alternate pathway complement activation. Thus, our discovery has important implications for GBS pathogenicity, immunogenicity, and vaccine design.
capsular polysaccharide, O-acetylation, roup B Streptococcus, Neuraminic Acids
NCBI PubMed ID: 15263085Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: varkiadmin@ucsd.edu
Institutions: Division of Biological Sciences, Glycobiology Research and Training Center, University of California at San Diego, La Jolla, CA 92093-0687, USA
Methods: PCR, ELISA, ESI-MS, MALDI-TOF MS, HPLC
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2. Compound ID: 12883
|
/Variants 0/-a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-+
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-4)-b-D-Glcp-(1-4)-b-D-Galp-(1-
/Variants 0/ is:
?%Ac-9)-
OR (exclusively)
?%Ac-8)-
OR (exclusively)
?%Ac-7)- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141588,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_241113,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
The structure is contained in the following publication(s):
- Article ID: 5129
Berti F, De Ricco R, Rappuoli R "Role of O-Acetylation in the Immunogenicity of Bacterial Polysaccharide Vaccines" -
Molecules 23(6) (2018) 1340
The incidence of infectious diseases caused by several bacterial pathogens such as Haemophilus influenzae type b, Streptococcus pneumoniae, and Neisseria meningitidis, has been dramatically reduced over the last 25 years through the use of glycoconjugate vaccines. The structures of the bacterial capsular polysaccharide (CPS) antigens, extracted and purified from microbial cultures and obtained with very high purity, show that many of them are decorated by O-acetyl groups. While these groups are often considered important for the structural identity of the polysaccharides, they play a major role in the functional immune response to some vaccines such as meningococcal serogroup A and Salmonella typhi Vi, but do not seem to be important for many others, such as meningococcal serogroups C, W, Y, and type III Group B Streptococcus. This review discusses the O-acetylation status of CPSs and its role in the immunological responses of these antigens.
O-acetylation, Bacterial polysaccharide, conjugate vaccines, Bacterial Vaccines, carbohydrate antigens
NCBI PubMed ID: 29865239Publication DOI: 10.3390/molecules23061340Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: rino.x.rappuoli@gsk.com
Institutions: External R&D, GSK Vaccines, 53100 Siena, Italy, External R&D, GSK Vaccines, 53100 Siena, Ital
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3. Compound ID: 12885
|
/Variants 0/-a-Neup5Ac-(2-3)-+ b-D-Galp-(1-6)-+
| |
-3)-b-D-Glcp-(1-2)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-
/Variants 0/ is:
?%Ac-9)-
OR (exclusively)
?%Ac-8)-
OR (exclusively)
?%Ac-7)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_153201,IEDB_153218,IEDB_153543,IEDB_156493,IEDB_190606,IEDB_241113,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
The structure is contained in the following publication(s):
- Article ID: 5129
Berti F, De Ricco R, Rappuoli R "Role of O-Acetylation in the Immunogenicity of Bacterial Polysaccharide Vaccines" -
Molecules 23(6) (2018) 1340
The incidence of infectious diseases caused by several bacterial pathogens such as Haemophilus influenzae type b, Streptococcus pneumoniae, and Neisseria meningitidis, has been dramatically reduced over the last 25 years through the use of glycoconjugate vaccines. The structures of the bacterial capsular polysaccharide (CPS) antigens, extracted and purified from microbial cultures and obtained with very high purity, show that many of them are decorated by O-acetyl groups. While these groups are often considered important for the structural identity of the polysaccharides, they play a major role in the functional immune response to some vaccines such as meningococcal serogroup A and Salmonella typhi Vi, but do not seem to be important for many others, such as meningococcal serogroups C, W, Y, and type III Group B Streptococcus. This review discusses the O-acetylation status of CPSs and its role in the immunological responses of these antigens.
O-acetylation, Bacterial polysaccharide, conjugate vaccines, Bacterial Vaccines, carbohydrate antigens
NCBI PubMed ID: 29865239Publication DOI: 10.3390/molecules23061340Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: rino.x.rappuoli@gsk.com
Institutions: External R&D, GSK Vaccines, 53100 Siena, Italy, External R&D, GSK Vaccines, 53100 Siena, Ital
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4. Compound ID: 12886
|
/Variants 0/-a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-+
|
-6)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-
/Variants 0/ is:
?%Ac-9)-
OR (exclusively)
?%Ac-8)-
OR (exclusively)
?%Ac-7)- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
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_241113,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
The structure is contained in the following publication(s):
- Article ID: 5129
Berti F, De Ricco R, Rappuoli R "Role of O-Acetylation in the Immunogenicity of Bacterial Polysaccharide Vaccines" -
Molecules 23(6) (2018) 1340
The incidence of infectious diseases caused by several bacterial pathogens such as Haemophilus influenzae type b, Streptococcus pneumoniae, and Neisseria meningitidis, has been dramatically reduced over the last 25 years through the use of glycoconjugate vaccines. The structures of the bacterial capsular polysaccharide (CPS) antigens, extracted and purified from microbial cultures and obtained with very high purity, show that many of them are decorated by O-acetyl groups. While these groups are often considered important for the structural identity of the polysaccharides, they play a major role in the functional immune response to some vaccines such as meningococcal serogroup A and Salmonella typhi Vi, but do not seem to be important for many others, such as meningococcal serogroups C, W, Y, and type III Group B Streptococcus. This review discusses the O-acetylation status of CPSs and its role in the immunological responses of these antigens.
O-acetylation, Bacterial polysaccharide, conjugate vaccines, Bacterial Vaccines, carbohydrate antigens
NCBI PubMed ID: 29865239Publication DOI: 10.3390/molecules23061340Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: rino.x.rappuoli@gsk.com
Institutions: External R&D, GSK Vaccines, 53100 Siena, Italy, External R&D, GSK Vaccines, 53100 Siena, Ital
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Total list of corresponding CSDB IDs (record IDs):
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