4-Methylumbelliferyl-α-Glycosides of Partially0-AcetylatedN-Acetylneuraminic Acids as Substrates of Bacterial and Viral Sialidases
- 1 January 1990
- journal article
- research article
- Published by Walter de Gruyter GmbH in Biological Chemistry Hoppe-Seyler
- Vol. 371 (2), 715-720
- https://doi.org/10.1515/bchm3.1990.371.2.715
Abstract
4-O-Acetylated, 7-O-acetylated, and 9-O-acetylated 4-methylumbelliferyl-alpha-N-acetyl-neuraminic acids (Neu4,5Ac2-MU, Neu5,7Ac2-MU, Neu5,9Ac2-MU) were tested as substrates of sialidases of Vibrio cholerae and of Clostridium perfringens. Both sialidases were unable to hydrolyse Neu4,5Ac2-MU. This compound at 1 mM concentration did not inhibit significantly the cleavage of Neu5Ac-MU, the best substrate tested. The 4-O-acetylated sialic acid glycoside is hydrolysed slowly by the sialidase from fowl plague virus. The relative substrate specificity, reflected in V/Km of the Vibrio cholerae sialidase is Neu5Ac-MU much greater than Neu5,7Ac2-MU approximately Neu5,9Ac2-MU and of the clostridial enzyme it is Neu5Ac-MU greater than Neu5,9Ac2-MU greater than Neu5,7Ac2-MU. The affinities of both enzymes for the side-chain O-acetylated sialic acid derivatives are higher than for Neu5Ac-MU. The artificial, well-defined substrates, described here, provide the opportunity to quantify the influence of sialic acid O-acetylation on the hydrolysis of sialoglycoconjugates without the side effects introduced by other parts of more complex glycans.Keywords
This publication has 7 references indexed in Scilit:
- Studies on sialic acids. XIX. Syntheses of partially O-acetylated 4-methylcoumarin-7-yl 5-acetamido-3,5-dideoxy-.ALPHA.-D-glycero-D-galacto-2-nonulopyranosidonic acids.CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
- Synthesis of 7-O-acetyl-N-acetylneuraminic acid derivative.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- O-acetylation of a cell-surface carbohydrate creates discrete molecular patterns during neural development.Proceedings of the National Academy of Sciences of the United States of America, 1987
- The Action of Sialidases on Substrates ContainingO-Acetylsialic AcidsBiological Chemistry Hoppe-Seyler, 1986
- Chemistry, Metabolism, and Biological Functions of Sialic AcidsAdvances in Carbohydrate Chemistry and Biochemistry, 1982
- “Neuraminidase-Resistant” Sialic Acid Residues of GangliosidesAdvances in experimental medicine and biology, 1980
- Zur Wirkungsspezifität der Neuraminidase. Das Verhalten isomerer N.O-Diacetyl-neuraminsäureglykoside im Submaxillarismucin von Pferd und Rind bei Einwirkung bakterieller NeuraminidaseHoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1968