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Literature DB >> 4748825

Kinetic studies on the acid hydrolysis of the methyl ketoside of unsubstituted and O-acetylated N-acetylneuraminic acid.

Abstract

The hydrolysis of the model compound 2-O-methyl-4,7,8,9-tetra-O-acetyl-N-acetyl-alpha-d-neuraminic acid and neuraminidase (Vibrio cholerae) closely resembled that of the O-acetylated sialic acid residues of rabbit Tamm-Horsfall glycoprotein. This confirmed that O-acetylation was responsible for the unusually slow rate of acid hydrolysis of O-acetylated sialic acid residues observed in rabbit Tamm-Horsfall glycoprotein and their resistance to hydrolysis by neuraminidase. The first-order rate constant of hydrolysis of 2-methyl-N-acetyl-alpha-d-neuraminic acid by 0.05m-H(2)SO(4) was 56-fold greater than that of 2-O-methyl-4,7,8,9-tetra-O-acetyl-N-acetyl -alpha-d-neuraminic acid. Kinetic studies have shown that in the pH range 1.00-3.30, the observed rate of hydrolysis of 2-methyl-N-acetyl-alpha-d-neuraminic acid can be attributed to acid-catalysed hydrolysis of the negatively charged CO(2) (-) form of the methyl ketoside.

Entities: Chemical Species

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Year: 1973 PMID： 4748825 PMCID： PMC1177751 DOI： 10.1042/bj1330623

Source DB: PubMed Journal: Biochem J ISSN： 0264-6021 Impact factor: 3.857

10 in total

5. Methods for the quantitative estimation of N-acetylneuraminic acid and their application to hydrolysates of sialomucoids.

Authors: D AMINOFF
Journal: Biochem J Date: 1961-11 Impact factor: 3.857

9. The sialic acids. XI. A periodate-resorcinol method for the quantitative estimation of free sialic acids and their glycosides.

Authors: G W Jourdian; L Dean; S Roseman
Journal: J Biol Chem Date: 1971-01-25 Impact factor: 5.157

10. The acid and enzymic hydrolysis of O-acetylated sialic acid residues from rabbit Tamm-Horsfall glycoprotein.

Authors: A Neuberger; W A Ratcliffe
Journal: Biochem J Date: 1972-09 Impact factor: 3.857

10 in total

1 in total

1. An autosomal dominant gene regulates the extent of 9-O-acetylation of murine erythrocyte sialic acids. A probable explanation for the variation in capacity to activate the human alternate complement pathway.

Authors: A Varki; S Kornfeld
Journal: J Exp Med Date: 1980-09-01 Impact factor: 14.307

1 in total

Kinetic studies on the acid hydrolysis of the methyl ketoside of unsubstituted and O-acetylated N-acetylneuraminic acid.

1. The thiobarbituric acid assay of sialic acids.

2. STUDIES ON THE STABILITY OF SIMPLE DERIVATIVES OF SIALIC ACID.

3. THE SENSITIVITY OF THE NEURAMINOSIDIC LINKAGE IN MUCOSUBSTANCES TOWARDS ACID AND TOWARDS NEURAMINIDASE.

4. Physical chemistry of mucins.

5. Methods for the quantitative estimation of N-acetylneuraminic acid and their application to hydrolysates of sialomucoids.

6. Quantitative estimation of sialic acids. II. A colorimetric resorcinol-hydrochloric acid method.

7. Configuration of the ketosidic bond of sialic acid.

8. The sialic acids of horse serum with special reference to their virus inhibitory properties.

9. The sialic acids. XI. A periodate-resorcinol method for the quantitative estimation of free sialic acids and their glycosides.

10. The acid and enzymic hydrolysis of O-acetylated sialic acid residues from rabbit Tamm-Horsfall glycoprotein.

1. An autosomal dominant gene regulates the extent of 9-O-acetylation of murine erythrocyte sialic acids. A probable explanation for the variation in capacity to activate the human alternate complement pathway.