Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: bacillary dysentery [ICD11:
1A02 
, ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
The structure was elucidated in this paperNCBI PubMed ID: 24376024Publication DOI: 10.1002/cbic.201300597Journal NLM ID: 100937360Publisher: Weinheim, Germany: Wiley Interscience
Correspondence: Sylvie.Armand
cermav.cnrs.fr
Institutions: Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS), Affiliated with Grenoble University and the Institut de Chimie Moléculaire de Grenoble, Domaine Universitaire de Grenoble, 601 rue de la Chimie, B.P. 53, 38041 Grenoble cedex 9, France, Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr. Roux, 75724 Paris Cedex 15, France, NRS UMR 3523, Institut Pasteur, 28 rue du Dr. Roux, 75724 Paris Cedex 15, France
We report the enzymatic synthesis of α-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside and α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranoside by using a wild-type transglucosidase in combination with glucoamylase and glucose oxidase. It was shown that Bacillus circulans 251 cyclodextrin glucanotransferase (CGTase, EC 2.1.4.19) can efficiently couple an α-L-rhamnosyl acceptor to a maltodextrin molecule with an α-(1→4) linkage, albeit in mixture with the α-(1→3) regioisomer, thus giving two glucosylated acceptors in a single reaction. Optimisation of the CGTase coupling reaction with β-cyclodextrin as the donor substrate and methyl or allyl α-L-rhamnopyranoside as acceptors resulted in good conversion yields (42-70 %) with adjustable glycosylation regioselectivity. Moreover, the efficient chemical conversion of the products of CGTase-mediated cis-glucosylation into protected building blocks (previously used in the synthesis of O-antigen fragments of several Shigella flexneri serotypes) was substantiated. These novel chemoenzymatic strategies towards useful, convenient intermediates in the synthesis of S. flexneri serotypes 2a and 3a oligosaccharides might find applications in developments towards synthetic carbohydrate-based vaccine candidates against bacillary dysentery.
carbohydrates, Shigella flexneri, biocatalysis, cis-glycosylation, cyclodextrin glucanotransferase
Structure type: oligomer
Location inside paper: p.293, scheme 2, compounds 6a and 6b EA-OR
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158539,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, chemical methods, MS, biochemical methods, enzymatic synthesis, cis-glycosylation
Biological activity: kinetic study of the coupling activity
Enzymes that release or process the structure: cyclodextrin glucanotransferase (CGTase, EC 2.1.4.19) from Bacillus circulans 251, glucoamylase, glucose oxidase, catalase
Synthetic data: enzymatic and chemoenzymatic
Comments, role: synthetic fragment of the O-antigen of S.flexneri 3a
Related record ID(s): 30147, 30520, 30521
NCBI Taxonomy refs (TaxIDs): 424717
Show glycosyltransferases
1H NMR data: present in publication
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13C NMR data: present in publication
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There is only one chemically distinct structure:
Found 
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