Chemoenzymatic Syntheses of Sialylated Oligosaccharides Containing C5-Modified Neuraminic Acids for Dual Inhibition of Hemagglutinins and Neuraminidases
作者： Lémonia Birikaki , Stéphanie Pradeau , Sylvie Armand , Bernard Priem , Luis Márquez-Domínguez
关键词: Sialidase 、 Maackia 、 Neuraminidase 、 Neuraminic acid 、 Stereochemistry 、 Agglutinin 、 Ganglioside 、 Escherichia coli 、 Vibrio cholerae 、 Biochemistry 、 Chemistry 、 General chemistry
摘要: A fast chemoenzymatic synthesis of sialylated oligosaccharides containing C5-modified neuraminic acids is reported. Analogues GM3 and GM2 ganglioside saccharidic portions where the acetyl group NeuNAc has been replaced by a phenylacetyl (PhAc) or propanoyl (Prop) moiety have efficiently prepared with metabolically engineered E. coli bacteria. analogues were either obtained chemoselective modification biosynthetic N-acetyl-sialyllactoside (GM3 NAc) direct bacterial using acid precursors. The latter strategy proved to be very versatile as it led an efficient analogues. These glycomimetics assessed against hemagglutinins sialidases. In particular, NPhAc displayed binding affinity for Maackia amurensis agglutinin (MAA) similar that NAc, while being resistant hydrolysis Vibrio cholerae (VC) neuraminidase. preliminary study influenza viruses also confirmed selective inhibition N1 neuraminidase NPhAc, suggesting potential developments detection flu fighting them.
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