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Zhang L, Muthana MM, Yu H, McArthur JB, Qu J, Chen X
Characterizing non-hydrolyzing Neisseria meningitidis serogroup A UDP-N-acetylglucosamine (UDP-GlcNAc) 2-epimerase using UDP-N-acetylmannosamine (UDP-ManNAc) and derivatives
Carbohydrate Research 419 (2016)
18-28
Neisseria meningitidis A
(NCBI TaxID 65699,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: bacterial septicemia [ICD11:
MA15.Y 
];
meningitis [ICD11:
1D01 ];
infection due to Neisseria meningitidis [ICD11:
XN1DV ]
NCBI PubMed ID: 26598987Publication DOI: 10.1016/j.carres.2015.10.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: xiichen
ucdavis.edu
Institutions: Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, CA 95616, USA
Neisseria meningitidis serogroup A non-hydrolyzing uridine 5'-diphosphate-N-acetylglucosamine (UDP-GlcNAc) 2-epimerase (NmSacA) catalyzes the interconversion between UDP-GlcNAc and uridine 5'-diphosphate-N-acetylmannosamine (UDP-ManNAc). It is a key enzyme involved in the biosynthesis of the capsular polysaccharide [-6ManNAcα1-phosphate-]n of N. meningitidis serogroup A, one of the six serogroups (A, B, C, W-135, X, and Y) that account for most cases of N. meningitidis-caused bacterial septicemia and meningitis. N. meningitidis serogroup A is responsible for large epidemics in the developing world, especially in Africa. Here we report that UDP-ManNAc could be used as a substrate for C-terminal His6-tagged recombinant NmSacA (NmSacA-His6) in the absence of UDP-GlcNAc. NmSacA-His6 was activated by UDP-GlcNAc and inhibited by 2-acetamidoglucal and UDP. Substrate specificity study showed that NmSacA-His6 could tolerate several chemoenzymatically synthesized UDP-ManNAc derivatives as substrates although its activity was much lower than non-modified UDP-ManNAc. Homology modeling and molecular docking revealed likely structural determinants of NmSacA substrate specificity. This is the first detailed study of N. meningitidis serogroup A UDP-GlcNAc 2-epimerase.
Neisseria meningitidis, capsular polysaccharide, epimerization, modeling, meningitis, UDP-GlcNAc, UDP-GlcNAc 2-epimerase, UDP-ManNAc
Structure type: homopolymer
Location inside paper: p.18
Trivial name: oligosaccharide repeating unit, repeating unit of capsular polysaccharide
Compound class: CPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_149549,IEDB_149550,IEDB_149551,IEDB_149552
Methods: 13C NMR, 1H NMR, NMR-2D, SDS-PAGE, kinetics assays, 31P NMR, ESI-MS, chemical synthesis, genetic methods, biochemical methods, enzyme assay, chemoenzymatic synthesis
Biosynthesis and genetic data: the cloning, expression, characterization of NmSacA, an N. meningitidis serogroup A non-hydrolyzing UDP-GlcNAc 2-epimerase
3D data: 3D data
NCBI Taxonomy refs (TaxIDs): 65699Reference(s) to other database(s): GTC:G20238HN, GlycomeDB:
25952
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There is only one chemically distinct structure:
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Mondal PK, Liao G, Mondal MA, Guo Z
Chemical synthesis of the repeating unit of type ia group B streptococcus capsular polysaccharide
Organic Letters 17(5) (2015)
1102-1105
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-+
|
-4)-b-D-Glcp-(1-4)-b-D-Galp-(1- |
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Streptococcus agalactiae B Ia
(NCBI TaxID 355315,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: bacterial septicemia [ICD11:
MA15.Y ];
meningitis [ICD11:
1D01 ];
infection due to Streptococcus agalactiae [ICD11:
XN0KC ]
NCBI PubMed ID: 25674920Publication DOI: 10.1021/ol5036563Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: zwguo
chem.wayne.edu
Institutions: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States
The structure of the capsular polysaccharide (CPS) of serotype Ia group B Streptococcus (GBS) has been characterized for years, but its repeating unit, which is a challenging pentasaccharide with a branch and a difficult α-sialic acid linkage, has not been synthesized yet. In this report, an effective synthesis was developed for the serotype Ia GBS CPS repeating unit, which had a reactive functionality linked to its main-chain reducing end to enable further elaboration, such as coupling with carrier proteins. The target molecule was accomplished by a convergent [2 + 3] glycosylation strategy employing a sialo-disaccharide as donor and a branched trisaccharide as acceptor. The strategy was designed to suit the synthesis of oligomers of the repeating unit.
capsular polysaccharide, glycosylation, Streptococcus agalactiae
Structure type: polymer chemical repeating unit
Location inside paper: p.1102, fig.1
Trivial name: PS-Ia
Compound class: CPS, EPS
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_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: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, NMR-1D, glycosylation
Comments, role: published polymerization frame was shifted for conformity with other records.
Related record ID(s): 30818
NCBI Taxonomy refs (TaxIDs): 355315Reference(s) to other database(s): GTC:G97670WK, GlycomeDB:
15760
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Mondal PK, Liao G, Mondal MA, Guo Z
Chemical synthesis of the repeating unit of type ia group B streptococcus capsular polysaccharide
Organic Letters 17(5) (2015)
1102-1105
|
b-D-Glcp-(1-4)-+
|
a-Neup5Ac-(2-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-1)-EtN |
Show graphically |
Streptococcus agalactiae B Ia
(NCBI TaxID 355315,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: bacterial septicemia [ICD11:
MA15.Y ];
meningitis [ICD11:
1D01 ];
infection due to Streptococcus agalactiae [ICD11:
XN0KC ]
The structure was elucidated in this paperNCBI PubMed ID: 25674920Publication DOI: 10.1021/ol5036563Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: zwguo
chem.wayne.edu
Institutions: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States
The structure of the capsular polysaccharide (CPS) of serotype Ia group B Streptococcus (GBS) has been characterized for years, but its repeating unit, which is a challenging pentasaccharide with a branch and a difficult α-sialic acid linkage, has not been synthesized yet. In this report, an effective synthesis was developed for the serotype Ia GBS CPS repeating unit, which had a reactive functionality linked to its main-chain reducing end to enable further elaboration, such as coupling with carrier proteins. The target molecule was accomplished by a convergent [2 + 3] glycosylation strategy employing a sialo-disaccharide as donor and a branched trisaccharide as acceptor. The strategy was designed to suit the synthesis of oligomers of the repeating unit.
capsular polysaccharide, glycosylation, Streptococcus agalactiae
Structure type: oligomer
Location inside paper: abstract, p.1103, compound 2
Trivial name: repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_1075132,IEDB_120354,IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141588,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,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_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, NMR-1D, glycosylation
Synthetic data: chemical
Comments, role: repeating unit
Related record ID(s): 30641
NCBI Taxonomy refs (TaxIDs): 355315
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1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
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