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Hu Z, Biagini M, Barel LA, Le Heiget G, Ben Imeddourene A, Le Guen Y, Monties N, Guerreiro C, Remaud-Simeon M, Moulis C, Andre I, Mulard LA
Convergent Chemoenzymatic Strategy to Deliver a Diversity of Shigella flexneri Serotype-Specific O-Antigen Segments from a Unique Lightly Protected Tetrasaccharide Core
Journal of Organic Chemistry 86(3) (2021)
2058-2075
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a-D-Glcp-(1-6)-+
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
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Shigella flexneri 4a
(NCBI TaxID 984898,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella flexneri [ICD11:
XN7Y2 
]
NCBI PubMed ID: 32700907Publication DOI: 10.1021/acs.joc.0c00777Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: isabelle.andre
insa-toulouse.fr
Institutions: Unité de Chimie des Biomolécules, Institut Pasteur, UMR3523 CNRS, 28 Rue du Dr Roux, 75724 Paris Cedex 15, France, Toulouse Biotechnology Institute, TBI, Université de Toulouse, CNRS, INRA, INSA, Toulouse, France. 135, Avenue de Rangueil, F-31077 Toulouse Cedex 04, France, Université Paris Descartes, Sorbonne Paris Cité, 75006 Paris, France, Université Paris 13, Sorbonne Paris Cité, 93430 Paris, France
Progress in glycoscience is strongly dependent on the availability of broadly diverse tailor-made, well-defined, and often complex oligosaccharides. Herein, going beyond natural resources and aiming to circumvent chemical boundaries in glycochemistry, we tackle the development of an in vitro chemoenzymatic strategy holding great potential to answer the need for molecular diversity characterizing microbial cell-surface carbohydrates. The concept is exemplified in the context of Shigella flexneri, a major cause of diarrhoeal disease. Aiming at a broad serotype coverage S. flexneri glycoconjugate vaccine, a non-natural lightly protected tetrasaccharide was designed for compatibility with (i) serotype-specific glucosylations and O-acetylations defining S. flexneri O-antigens, (ii) recognition by suitable α-transglucosylases, and (iii) programmed oligomerization following enzymatic α-d-glucosylation. The tetrasaccharide core was chemically synthesized from two crystalline monosaccharide precursors. Six α-transglucosylases found in the glycoside hydrolase family 70 were shown to transfer glucosyl residues on the non-natural acceptor. The successful proof of concept is achieved for a pentasaccharide featuring the glucosylation pattern from the S. flexneri type IV O-antigen. It demonstrates the potential of appropriately planned chemoenzymatic pathways involving non-natural acceptors and low-cost donor/transglucosylase systems to achieve the demanding regioselective α-d-glucosylation of large substrates, paving the way to microbial oligosaccharides of vaccinal interest.
core, tetrasaccharide, serotype, O-antigen, Oligosaccharides, pentasaccharide, vaccine, S.flexneri
Structure type: suggested polymer biological repeating unit
Location inside paper: abstract, Fig. 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, UV, RP-HPLC, enzymatic glucosylation, HR-ESI-MS
NCBI Taxonomy refs (TaxIDs): 984898Reference(s) to other database(s): GTC:G27937NZ, GlycomeDB:
3533
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Salamone S, Guerreiro C, Cambon E, Andre I, Remaud-Simeon M, Mulard LA
Programmed chemo-enzymatic synthesis of the oligosaccharide component of a carbohydrate-based antibacterial vaccine candidate
Chemical Communications 51(13) (2015)
2581-2584
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Shigella flexneri
(NCBI TaxID 623,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacillary dysentery (shigellosis) [ICD11:
1A02 , ICD11:
SA56 , ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
NCBI PubMed ID: 25569152Publication DOI: 10.1039/c4cc08805kJournal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
Correspondence: laurence.mulard
pasteur.fr
Institutions: Université de Toulouse, INSA, UPS, INP, LISBP, 135 Avenue de Rangueil, F-31077 Toulouse, France, CNRS, UMR5504, F-31400 Toulouse, France, Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France, CNRS UMR 3523, Institut Pasteur, F-75015 Paris, France, INRA, UMR792 Ingénierie des Systèmes Biologiques et des Procédés, F-31400 Toulouse, France
The powerful chemo-enzymatic synthesis of the pentadecasaccharide hapten involved in the first synthetic carbohydrate-based vaccine candidate against endemic shigellosis is reported. The high yielding site-selective α-D-glucosylation of a lightly protected disaccharide by an engineered transglucosylase-sucrose system gave a trisaccharide, which was chemically elongated by an efficient [5+5] process.
synthesis, oligosaccharide, Shigella flexneri, vaccine
Structure type: polymer chemical repeating unit
Location inside paper: p.2581, fig.1(a)
Compound class: O-polysaccharide, O-antigen, Shigella serogroup Y antigen, rhamnoglucan
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_143253,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, HPLC, UV, glycosylation, acetylation, RP-HPLC, ESI-TOF-MS, enzymatic glucosylation
Comments, role: S. flexneri O-Ag backbone.
Related record ID(s): 30856
NCBI Taxonomy refs (TaxIDs): 623Reference(s) to other database(s): GTC:G98477AV, GlycomeDB:
3543, CCSD:
2501, CBank-STR:8288, GenDB:AFl28887
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Salamone S, Guerreiro C, Cambon E, Andre I, Remaud-Simeon M, Mulard LA
Programmed chemo-enzymatic synthesis of the oligosaccharide component of a carbohydrate-based antibacterial vaccine candidate
Chemical Communications 51(13) (2015)
2581-2584
|
a-D-Glcp-(1-4)-+
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Shigella flexneri 2a
(NCBI TaxID 42897,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacillary dysentery (shigellosis) [ICD11:
1A02 , ICD11:
SA56 , ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
The structure was elucidated in this paperNCBI PubMed ID: 25569152Publication DOI: 10.1039/c4cc08805kJournal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
Correspondence: laurence.mulard
pasteur.fr
Institutions: Université de Toulouse, INSA, UPS, INP, LISBP, 135 Avenue de Rangueil, F-31077 Toulouse, France, CNRS, UMR5504, F-31400 Toulouse, France, Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France, CNRS UMR 3523, Institut Pasteur, F-75015 Paris, France, INRA, UMR792 Ingénierie des Systèmes Biologiques et des Procédés, F-31400 Toulouse, France
The powerful chemo-enzymatic synthesis of the pentadecasaccharide hapten involved in the first synthetic carbohydrate-based vaccine candidate against endemic shigellosis is reported. The high yielding site-selective α-D-glucosylation of a lightly protected disaccharide by an engineered transglucosylase-sucrose system gave a trisaccharide, which was chemically elongated by an efficient [5+5] process.
synthesis, oligosaccharide, Shigella flexneri, vaccine
Structure type: polymer chemical repeating unit ; 2493.9602 [M+Na]+, n=3
C
98H
166N
4O
67Location inside paper: p.2581, fig.1(b), p.2583, scheme 1, compound 1
Aglycon: 2-aminoethyl
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_130687,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135806,IEDB_135807,IEDB_135808,IEDB_135809,IEDB_135813,IEDB_135817,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, HPLC, UV, glycosylation, acetylation, RP-HPLC, ESI-TOF-MS, enzymatic glucosylation
Synthetic data: chemical and enzymatic
Comments, role: Synthetic the pentadecasaccharide hapten (1) as a vaccine candidate against endemic shigellosis.
Related record ID(s): 30665
NCBI Taxonomy refs (TaxIDs): 42897Reference(s) to other database(s): GTC:G13476UX
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