Zur Biosynthese derN-Glykolyl-neuraminsäure. Die oxydative Entstehung vonN-Glykolyl-neuraminsäure ausN-Acetyl-neuraminsäure

Schoop, Hans Joseph; Schauer, Roland; Faillard, Hans

doi:10.1515/bchm2.1969.350.1.155

Cited by 45 publications

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“…In other tissues of the body it has been estimated that the portion of free sialic acid is approximately 1-2 % of the total sialic acid concentration (Schoop et al, 1969).…”

Section: Free Sialic Acid In the Human Body And In Breast Milkmentioning

confidence: 99%

The nutritional role of free sialic acid, a human milk monosaccharide, and its application as a functional food ingredient

Röhrig¹,

Choi

Baldwin

2016

Critical Reviews in Food Science and Nutrition

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N-Acetyl-d-neuraminic acid (NANA), more commonly known by its trivial name sialic acid, is an endogenous human and ubiquitous nutritional monosaccharide. As a bound sugar at the terminal positions of glycans NANA is known to play important roles in many biological events. The data that exist on the occurrence of the free monosaccharide in breast milk and nutrition, however, are less commonly discussed. In most foods of animal origin, sialic acid occurs as a mixture of NANA and N-glycolyl-d-neuraminic acid (NGNA), a hydroxylated derivative of NANA that is not found in humans. The dietary intake of NGNA has been identified as a risk factor for long-term adverse health effects. Therefore, we present summaries on the biochemistry, metabolism, bioavailability, and the data on NANA and NGNA levels that occur in diverse foods. Finally, we discuss the emerging data demonstrating that free NANA is linked to positive nutritional effects including pronounced antioxidative properties. These data and the extremely high safety profile of NANA justify dietary enrichment at levels that correspond to the dietary intake of NANA in infants through breast milk.

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“…In other tissues of the body it has been estimated that the portion of free sialic acid is approximately 1-2 % of the total sialic acid concentration (Schoop et al, 1969).…”

Section: Free Sialic Acid In the Human Body And In Breast Milkmentioning

confidence: 99%

The nutritional role of free sialic acid, a human milk monosaccharide, and its application as a functional food ingredient

Röhrig¹,

Choi

Baldwin

2016

Critical Reviews in Food Science and Nutrition

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“…The simplest explanation may be that the hydroxylase which converts NeuNAc to NeuNGl [3,34] is not absolutely specific for N-acetyl groups but can also react with 0-acetyl groups. This hypothesis is at present under investigation.…”

Section: Origin Qf'the 0-acyz Groupsmentioning

confidence: 99%

“…The glycoloyl group is formed by hydroxylation of N-acetylneuraminic acid [3]. In addition to the N-acylneuraminic acids, various N-acetyl-0-acetylneuraminic acids have been isolated from different biological sources.…”

mentioning

confidence: 99%

New Sialic Acids

Buscher

Casals-Stenzel

Schauer

1974

European Journal of Biochemistry

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101

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1. Sialic acids were released by dilute acids or by neuraminidase from glycoproteins of bovine and equine submandibular glands, from glycoproteins of equine blood plasma and from equine erythrocyte membranes. They were purified by ion-exchange chromatography and fractionated on cellulose.2. The following methods have been adapted to the structural analysis of sialic acids with regard to the nature and position of the N-acyl and 0-acyl groups. a) Thin-layer chromatography in two dimensions with intermediate ammonia treatment to remove the 0-acyl groups leading to the identification of the basic N-acylneuraniinic acids.b) Thin-layer chromatography in two dimensions with intermediate hydroxylamine treatment allowing the identification of the 0-acyl groups of sialic acids as hydroxamates. c) Gas-liquid chromatography for identification of the different N-acylated and 0-acylated sialic acids.3. The structure of the following new sialic acids have been established: a) N-glycoloyl-8-0-acetylneuraminic acid isolated from glycoproteins of bovine submandibular glands; b) N-acetyl-4-0-glycoloylneuraminic acid isolated from glycoproteins of equine submandibular glands and also occurring in equine blood plasma and equine erythrocyte membranes; c) N-acetyl-7 or 8-0-glycoloylneuraminic acid detected in glycoproteins from bovine submandibular glands.4. The 0-acetylated N-glycoloylneuraminic acid first detected in horse erythrocyte membranes by Hakomori and Saito and in horse serum by Pepper, was determined to be N-glycoloyl-4-0-acetylneuraminic acid; it was also found to occur in submandibular glands of horse.5. The sialic acid patterns from the different biological materials investigated are compared.

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“…2 · 13 ). They were separated from the membranes or the cytosole glycoprotein fraction by centrifugation or by dialysis respectively.…”

Section: Preparation Of N-glycoloyl-and N-acetylneuraminic Acids and mentioning

confidence: 99%

Studies on the Subcellular Site of the Biosynthesis of N-Glycoloylneuraminic Acid in Porcine Submaxillary Gland

Schauer¹,

Wember²

1970

Hoppe-Seyler´s Zeitschrift für physiologische Chemie

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Slices of porcine submaxillary gland were incubated for periods ranging from 5 min to 4 h with [l-14 C]acetate in an atmosphere of oxygen. Subcellular membranes and the cytosole with the soluble glycoprotein were prepared afterwards by differential centrifugation. Both the glycoprotein-bound acylneuraminic acids of the membranes and of the cytosole compartment consisted of about 90% TV-glycoloyl-and 10% N-acetylneuraminic acid. After 5 min of incubation only the W-acetyl-and Af-glycoloylneuraminic acids of the membraneous glycoprotein were labelled. Following a longer incubation period the specific radioactivities of the acylneuraminic acids of the membranes were 3-to 20-fold higher than those of the acylneuraminic acids in the cytosole glycoprotein. Puromycin (5 X 10~4M) depressed the spe-Zusammenfassung: Untersuchungen über den subzellulären Biosyntheseort der N-Glykoloylneuraminsäure in Schweine-Submaxillaris-Drüsen. Überlebende Schnitte der Submaxillarisdrüse vom Schwein werden 5 min bis 4 h lang mit [l-14 C]Acetat unter O2 inkubiert. Durch fraktionierte Zentrifugation werden subzelluläre Membranen ("Mikrosomen") und das Cytosol mit löslichem Glykoprotein gewonnen. Die an das Glykoprotein dieser beiden zellulären Kompartimente gebundene 7V-Glykoloyl-und TV-Acetylneuraminsäure werden isoliert und auf ihre radioaktive Markierung untersucht. Sowohl die Glykoprotein-gebundenen Acylneuraminsäuren der subzellulären Membranen (Anteil an den Gesamtneuram insäuren des Drüsengewebes ca. 2-3 %) als auch des löslichen Glykoproteins im Cytosol bestehen aus ca. 90% JV-Glykoloyl-und ca. 10% 7V-Acetylneuraminsäure. cific radioactivities of glycosidically bound cytosole 7V-glycoloyl-and 7V-acetylneuraminic acids by 77 % and those of the membranes only by 24% when compared with the control experiment. Puromycin had no inhibitory effect on the metabolic pool of "free" 7V-glycoloylneuraminic acid in the porcine gland. The specific radioactivity of free 7V-glycoloylneuraminic acid was about 7-times higher than that of membrane-bound 7V-glycoloylneuraminic acid after l h of incubation. A model is proposed in which A/-glycoloyI-and TV-acetylneuraminic acids are transferred only to the growing glycoprotein-chains still attached to Subcellular membranes. The complete glycoprotein is thereafter released from the membranes and stored in the cytosole.

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Zur Biosynthese derN-Glykolyl-neuraminsäure. Die oxydative Entstehung vonN-Glykolyl-neuraminsäure ausN-Acetyl-neuraminsäure

Cited by 45 publications

References 0 publications

The nutritional role of free sialic acid, a human milk monosaccharide, and its application as a functional food ingredient

The nutritional role of free sialic acid, a human milk monosaccharide, and its application as a functional food ingredient

New Sialic Acids

Studies on the Subcellular Site of the Biosynthesis of N-Glycoloylneuraminic Acid in Porcine Submaxillary Gland

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