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Chemoenzymatic Syntheses of Sialylated Oligosaccharides Containing C5-Modified Neuraminic Acids for Dual Inhibition of Hemagglutinins and Neuraminidases.
- Source :
- Chemistry - A European Journal; 7/20/2015, Vol. 21 Issue 30, p10903-10912, 10p
- Publication Year :
- 2015
-
Abstract
- A fast chemoenzymatic synthesis of sialylated oligosaccharides containing C5-modified neuraminic acids is reported. Analogues of GM<subscript>3</subscript> and GM<subscript>2</subscript> ganglioside saccharidic portions where the acetyl group of Neu NAc has been replaced by a phenylacetyl (PhAc) or a propanoyl (Prop) moiety have been efficiently prepared with metabolically engineered E. coli bacteria. GM<subscript>3</subscript> analogues were either obtained by chemoselective modification of biosynthetic N-acetyl-sialyllactoside (GM<subscript>3</subscript> NAc) or by direct bacterial synthesis using C5-modified neuraminic acid precursors. The latter strategy proved to be very versatile as it led to an efficient synthesis of GM<subscript>2</subscript> analogues. These glycomimetics were assessed against hemagglutinins and sialidases. In particular, the GM<subscript>3</subscript> NPhAc displayed a binding affinity for Maackia amurensis agglutinin (MAA) similar to that of GM<subscript>3</subscript> NAc, while being resistant to hydrolysis by Vibrio cholerae ( VC) neuraminidase. A preliminary study with influenza viruses also confirmed a selective inhibition of N1 neuraminidase by GM<subscript>3</subscript> NPhAc, suggesting potential developments for the detection of flu viruses and for fighting them. [ABSTRACT FROM AUTHOR]
- Subjects :
- ENZYMATIC analysis
BACTERIA
VIRUSES
GANGLIOSIDES
CANCER treatment
Subjects
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 21
- Issue :
- 30
- Database :
- Complementary Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 108355091
- Full Text :
- https://doi.org/10.1002/chem.201500708