Biomaterial Database

Interaction of N-acetyl-4-epi-D-neuraminic acid with key enzymes of sialic acid metabolism. 1988

H J Gross, and A Kovac, and U Rose, and H Watzlawick, and R Brossmer

Institut für Biochemie II, Universität Heidelberg, Federal Republic of Germany.

In spite of the axially orientated hydroxy group at C-4, the benzyl alpha-glycoside of N-acetyl-4-epi-D-neuraminic acid (4-epi-NeuAc) is a substrate for sialidases from Vibrio cholerae, Clostridium perfringens, and Arthrobacter ureafaciens, although to an extent which differs depending on the enzyme. Surprisingly, V. cholerae sialidase is by far the slowest acting enzyme; this is in contrast to its usual behavior. Fowl plague virus sialidase and bovine testis sialidase also cleave this glycoside slowly. 4-Epi-NeuAc is not a substrate for N-acetylneuraminic acid aldolase from C. perfringens but reversibly inhibits the enzyme with a Ki = 2.3 mM. The N-acetylneuraminic acid analogue is not converted to the corresponding CMP-glycoside by CMP-sialic acid synthase from bovine brain; however, it is an effective reversible inhibitor of the enzyme. The kinetic properties were analyzed with an assay system at pH 9 as well as an assay system at pH 7.5. The results from Dixon and Hanes plots did not agree. Therefore, no conclusions about the mechanism of the inhibition could be reached. This is the first reported sialic acid analogue which can act as an inhibitor of CMP-sialic acid synthase.

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D009439	Neuraminidase	An enzyme that catalyzes the hydrolysis of alpha-2,3, alpha-2,6-, and alpha-2,8-glycosidic linkages (at a decreasing rate, respectively) of terminal sialic residues in oligosaccharides, glycoproteins, glycolipids, colominic acid, and synthetic substrate. (From Enzyme Nomenclature, 1992)	Sialidase,Exo-alpha-Sialidase,N-Acylneuraminate Glycohydrolases,Oligosaccharide Sialidase,Exo alpha Sialidase,Glycohydrolases, N-Acylneuraminate,N Acylneuraminate Glycohydrolases,Sialidase, Oligosaccharide
D002417	Cattle	Domesticated bovine animals of the genus Bos, usually kept on a farm or ranch and used for the production of meat or dairy products or for heavy labor.	Beef Cow,Bos grunniens,Bos indicus,Bos indicus Cattle,Bos taurus,Cow,Cow, Domestic,Dairy Cow,Holstein Cow,Indicine Cattle,Taurine Cattle,Taurus Cattle,Yak,Zebu,Beef Cows,Bos indicus Cattles,Cattle, Bos indicus,Cattle, Indicine,Cattle, Taurine,Cattle, Taurus,Cattles, Bos indicus,Cattles, Indicine,Cattles, Taurine,Cattles, Taurus,Cow, Beef,Cow, Dairy,Cow, Holstein,Cows,Dairy Cows,Domestic Cow,Domestic Cows,Indicine Cattles,Taurine Cattles,Taurus Cattles,Yaks,Zebus
D005470	Fluorometry	An analytical method for detecting and measuring FLUORESCENCE in compounds or targets such as cells, proteins, or nucleotides, or targets previously labeled with FLUORESCENCE AGENTS.	Fluorimetry,Fluorometric Analysis,Analysis, Fluorometric
D000216	N-Acylneuraminate Cytidylyltransferase	An enzyme that forms CMP-acylneuraminic acids, which donate the N-acylneuraminic acid residues to the terminal sugar residue of a ganglioside or glycoprotein. EC 2.7.7.43.	Acylneuraminate Cytidylyltransferase,CMP Sialate Pyrophosphorylase,CMP Sialate Synthase,CMP-N-Acetylneuraminic Acid Synthetase,CMP-Sialic Acid Synthetase,Cytidine 5'-Monophosphosialic Acid Synthetase,Cytidine 5-Monophosphosialate Synthase,CMP N Acetylneuraminic Acid Synthetase,CMP Sialic Acid Synthetase,Cytidine 5 Monophosphosialate Synthase,Cytidine 5' Monophosphosialic Acid Synthetase,Cytidylyltransferase, Acylneuraminate,Cytidylyltransferase, N-Acylneuraminate,N Acylneuraminate Cytidylyltransferase,Pyrophosphorylase, CMP Sialate,Sialate Pyrophosphorylase, CMP,Sialate Synthase, CMP,Synthase, CMP Sialate,Synthase, Cytidine 5-Monophosphosialate,Synthetase, CMP-N-Acetylneuraminic Acid,Synthetase, CMP-Sialic Acid
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012794	Sialic Acids	A group of naturally occurring N-and O-acyl derivatives of the deoxyamino sugar neuraminic acid. They are ubiquitously distributed in many tissues.	N-Acetylneuraminic Acids,Acids, N-Acetylneuraminic,Acids, Sialic,N Acetylneuraminic Acids
D013045	Species Specificity	The restriction of a characteristic behavior, anatomical structure or physical system, such as immune response; metabolic response, or gene or gene variant to the members of one species. It refers to that property which differentiates one species from another but it is also used for phylogenetic levels higher or lower than the species.	Species Specificities,Specificities, Species,Specificity, Species
D013053	Spectrophotometry	The art or process of comparing photometrically the relative intensities of the light in different parts of the spectrum.
D019158	N-Acetylneuraminic Acid	An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518)	Sialic Acid,Acid, N-Acetylneuraminic,Acid, Sialic,N Acetylneuraminic Acid