Synthesis of Neuraminidase‐Resistant Sialyllactose Mimetics from <i>N</i>‐Acyl Mannosamines using Metabolically Engineered <i>Escherichia coli</i> - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2023

Synthesis of Neuraminidase‐Resistant Sialyllactose Mimetics from N‐Acyl Mannosamines using Metabolically Engineered Escherichia coli

Résumé

Herein, we describe the efficient gram-scale synthesis of α2,3and α2,6-sialyllactose oligosaccharides as well as mimetics from N-acyl mannosamines and lactose in metabolically engineered bacterial cells grown at high cell density. We designed new Escherichia coli strains co-expressing sialic acid synthase and N-acylneuraminate cytidylyltransferase from Campylobacter jejuni together with the α2,3sialyltransferase from Neisseria meningitidis or the α2,6sialyltransferase from Photobacterium sp. JT-ISH-224. Using their mannose transporter, these new strains actively internalized N-acetylmannosamine (ManNAc) and its N-propanoyl (N-Prop), N-butanoyl (N-But) and N-phenylacetyl (N-PhAc) analogs and converted them into the corresponding sialylated oligosaccharides, with overall yields between 10 % and 39 % (200-700 mg.L À 1 of culture). The three α2,6-sialyllactose analogs showed similar binding affinity for Sambucus nigra SNAÀ I lectin as for the natural oligosaccharide. They also proved to be stable competitive inhibitors of Vibrio cholerae neuraminidase. These N-acyl sialosides therefore hold promise for the development of anti-adhesion therapy against influenza viral infections.
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Dates et versions

hal-04231571 , version 1 (06-10-2023)

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Paul Rivollier, Eric Samain, Sylvie Armand, Isabelle Jeacomine, Emeline Richard, et al.. Synthesis of Neuraminidase‐Resistant Sialyllactose Mimetics from N‐Acyl Mannosamines using Metabolically Engineered Escherichia coli. Chemistry - A European Journal, 2023, 29 (46), ⟨10.1002/chem.202301555⟩. ⟨hal-04231571⟩
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