CGTase-Catalysed cis -Glucosylation of L -Rhamnosides for the Preparation of Shigella flexneri 2a and 3a Haptens

Autor: Hugues Driguez, Carole Urbach, Catherine Guerreiro, Sami Halila, Laurence A. Mulard, Sylvie Armand
Přispěvatelé: Centre de Recherches sur les Macromolécules Végétales (CERMAV), Université Joseph Fourier - Grenoble 1 (UJF)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Chimie des Biomolécules - Chemistry of Biomolecules, Institut Pasteur [Paris] (IP)-Centre National de la Recherche Scientifique (CNRS), This work was supported by the French National Research Agency (ANR Project OPTIGLUC 2005–2008), We are grateful to Dr. Hans Leemhuis (University of Groningen) for providing the CGTase gene. We thank Dr. F. Lenouvel (CERMAV) for his help with CGTase purification and Dr. J. Boutet (Chimie des Biomolécules, CNRS URA 2128) for providing methyl α‐L‐rhamnopyranoside, Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), Institut Pasteur [Paris]-Centre National de la Recherche Scientifique (CNRS)
Jazyk: angličtina
Rok vydání: 2014
Předmět:
cis-glycosylation
MESH: Enzyme Stability
Glycosylation
[SDV.BIO]Life Sciences [q-bio]/Biotechnology
MESH: Shigella flexneri
carbohydrates
Oligosaccharides
Bacillus
Biochemistry
Shigella flexneri
chemistry.chemical_compound
Enzyme Stability
Organic chemistry
chemistry.chemical_classification
biology
Cyclodextrin
MESH: Kinetics
[CHIM.ORGA]Chemical Sciences/Organic chemistry
beta-Cyclodextrins
Temperature
Regioselectivity
MESH: Glycosylation
MESH: Temperature
cyclodextrin glucanotransferase
Carbohydrate Sequence
Glucosyltransferases
MESH: Haptens
Molecular Medicine
MESH: Biocatalysis
MESH: beta-Cyclodextrins
biocatalysis
Stereochemistry
Molecular Sequence Data
Coupling reaction
MESH: Bacillus
Molecular Biology
MESH: Carbohydrate Sequence
MESH: Glucosyltransferases
MESH: Molecular Sequence Data
Organic Chemistry
Substrate (chemistry)
[CHIM.CATA]Chemical Sciences/Catalysis
biology.organism_classification
carbohydrates (lipids)
Kinetics
chemistry
Biocatalysis
Bacillus circulans
Haptens
MESH: Oligosaccharides
Zdroj: ChemBioChem
ChemBioChem, 2014, 15 (2), pp.293-300. ⟨10.1002/cbic.201300597⟩
ChemBioChem, Wiley-VCH Verlag, 2014, 15 (2), pp.293-300. ⟨10.1002/cbic.201300597⟩
ISSN: 1439-4227
1439-7633
DOI: 10.1002/cbic.201300597⟩
Popis: International audience; 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.
Databáze: OpenAIRE
Externí odkaz: