Classification Term: 3734

N-acylneuraminic acids (ontology term: CHEMONTID:0003048)

Neuraminic acids carrying an N-acyl substituent." []

found 35 associated metabolites at no_class-level_10 metabolite taxonomy ontology rank level.

Ancestor: N-acylneuraminic acids and derivatives

Child Taxonomies: N-acylneuraminate-9-phosphates

N-acetylneuraminate

(4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2, 3-trihydroxypropyl]oxane-2-carboxylic acid

C11H19NO9 (309.106)


Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID A018; [MS2] KO008824 KEIO_ID A018 N-Acetylneuraminic acid is a sialic acid monosaccharide ubiquitous on cell membrane glycoproteins and glycolipids of mammalian cell ganglioglycerides, which plays a biological role in neurotransmission, leukocyte vasodilation, and viral or bacterial infection.

   

N-Acetyl-7-O-acetylneuraminic acid

(2S,4S,5R,6R)-6-[(1R,2R)-1-(Acetyloxy)-2,3-dihydroxypropyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate

C13H21NO10 (351.1165)


N-Acetyl-7-O-acetylneuraminic acid is a component of glycoprotein- and glycolipid-bound sialic acids present in the human erythrocyte membrane (RBC). (PMID: 12527384). N-Acetyl-7-O-acetylneuraminic acid has been detected in basaliomas and normal human skin. (PMID: 11180001). Determination of N-Acetyl-7-O-acetylneuraminic acid in human serum has been obtained by fluorometric high-performance liquid chromatography. (PMID: 2757191). N-Acetyl-7-O-acetylneuraminic acid is a component of glycoprotein- and glycolipid-bound sialic acids present in the human erythrocyte membrane (RBC). (PMID: 12527384)

   

N-Acetylneuraminate 9-phosphate

(4R,5S,6S)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

C11H20NO12P (389.0723)


N-Acetylneuraminate 9-phosphate is an intermediate in Aminosugars metabolism. N-Acetylneuraminate 9-phosphate is the 4th to last step in the synthesis of colominate and is converted from N-Acetyl-D-mannosamine-6-phosphate via the enzyme N-Acylneuraminate-9-phosphate synthase (EC 2.5.1.57). It is then converted to N-Acetylneuraminate via the enzyme N-acylneuraminate-9-phosphatase(EC 3.1.3.29). [HMDB] N-Acetylneuraminate 9-phosphate is an intermediate in Aminosugars metabolism. N-Acetylneuraminate 9-phosphate is the 4th to last step in the synthesis of colominate and is converted from N-Acetyl-D-mannosamine-6-phosphate via the enzyme N-Acylneuraminate-9-phosphate synthase (EC 2.5.1.57). It is then converted to N-Acetylneuraminate via the enzyme N-acylneuraminate-9-phosphatase(EC 3.1.3.29).

   

N-Acetyl-a-neuraminic acid

(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C11H19NO9 (309.106)


N-Acetyl-alpha-neuraminate is a sialic acid. Sialic acids are an important family of related 9-carbon sugars acids, present on the surface of many different cells and functioning in a wide range of different biological processes. They mediate a variety of cell-cell and cell-molecule interactions in eukaryotes and can be utilized by pathogens to evade the host immune response. N-acetylneuraminic acid is the most common sialic acid, and the predominant form present in humans. It can be found as a terminal sugar on a wide range of surface glycoconjugates. A number of bacteria that can colonize humans (such as E. coli) make use of N-acetylneuraminic acid as a nutrient source. N-Acetyl-a-neuraminic acid is a derivatized monosaccharide. Neuraminic acid derivatives are found widely distributed in animal tissues and in bacteria. The N- or O-substituted derivatives of neuraminic acid are collectively known as sialic acids, the predominant one being N-acetylneuraminic acid. [HMDB] N-Acetylneuraminic acid is a sialic acid monosaccharide ubiquitous on cell membrane glycoproteins and glycolipids of mammalian cell ganglioglycerides, which plays a biological role in neurotransmission, leukocyte vasodilation, and viral or bacterial infection.

   

Disialyllactose

(2S,4S,5R,6R)-2-{[(1S,2R)-1-[(2R,3R,4S,6S)-6-carboxy-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C34H56N2O27 (924.307)


Disialyllactose is a naturally occurring oligosaccharide present in the cell surface and in breast milk. Disialyllactose has been identified as one of the binding sites of the C fragment of the clostridial tetanus toxin, binding with great specificity and high affinity. Clostridial neurotoxins, botulinum and tetanus, gain entry into motor neurons by binding to the sialic or N-acetylneuraminic acid (NeuAc) residues of gangliosides and specific protein receptors attached to the cells surface. Neurotoxins interact with motor neurons, blocking acetylcholine release and causing muscle paralysis and death. The glycosidic linkage between Neu5Ac and other monosaccharides is susceptible to hydrolysis at low pH, and disialyl lactose is unstable under acidic conditions. (PMID: 16713287, 16104015, 7263800, 7972078) [HMDB] Disialyllactose is a naturally occurring oligosaccharide present in the cell surface and in breast milk. Disialyllactose has been identified as one of the binding sites of the C fragment of the clostridial tetanus toxin, binding with great specificity and high affinity. Clostridial neurotoxins, botulinum and tetanus, gain entry into motor neurons by binding to the sialic or N-acetylneuraminic acid (NeuAc) residues of gangliosides and specific protein receptors attached to the cells surface. Neurotoxins interact with motor neurons, blocking acetylcholine release and causing muscle paralysis and death. The glycosidic linkage between Neu5Ac and other monosaccharides is susceptible to hydrolysis at low pH, and disialyl lactose is unstable under acidic conditions. (PMID: 16713287, 16104015, 7263800, 7972078).

   

N-Acetyl-9-O-lactoylneuraminic acid

(2S,4S,5R,6R)-6-[(1R,2R)-1,2-Dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate

C14H23NO11 (381.1271)


N-Acetyl-9-O-lactoylneuraminic acid is a sialic acid produced by sialate 9-O-lactoyltransferases. Lactoylation of CMP-N-acetylneuraminic acid, N-acetylneuramimic acid and glycoconjugate-bound N-acetylneuramimic acid has been observed, with the glycoconjugate form being the best substrate. A sialic acid produced by sialate 9-O-lactoyltransferases. Lactoylation of CMP-N-acetylneuraminic acid, N-acetylneuramimic acid and glycoconjugate-bound N-acetylneuramimic acid has been observed, with the glycoconjugate form being the best substrate. [HMDB]

   

3'-Sialyllactose

(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C23H39NO19 (633.2116)


Sialyllactose is an oligossaccharide found in both human breast milk and cows milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin. [HMDB] Sialyllactose is an oligossaccharide found in both human breast milk and cows milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin.

   

3-Sialyl Lewis

(2S,4S,5R,6R)-2-{[(2R,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-5,6-dihydroxy-2-[(1-hydroxyethylidene)amino]-1-oxo-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C31H52N2O23 (820.2961)


3-Sialyl Lewis tetrasaccharide, is a tumor-associated carbohydrate antigen. It is used as a tumor marker in colon and pancreatic cancer. When the selectin family of adhesion molecules was described, it was found that 3-Sialyl Lewis, along with sialyl Lewis(x) antigen, is a ligand for E-selectin, responsible for adhesion of several types of human carcinoma cells to endothelium. It has been suggested that such interactions play an important role in the formation of metastases by colon and pancreatic cancer cells. (PMID:12362971) [HMDB] 3-Sialyl Lewis tetrasaccharide, is a tumor-associated carbohydrate antigen. It is used as a tumor marker in colon and pancreatic cancer. When the selectin family of adhesion molecules was described, it was found that 3-Sialyl Lewis, along with sialyl Lewis(x) antigen, is a ligand for E-selectin, responsible for adhesion of several types of human carcinoma cells to endothelium. It has been suggested that such interactions play an important role in the formation of metastases by colon and pancreatic cancer cells. (PMID:12362971). C307 - Biological Agent > C268 - Antigen > C912 - Tumor Antigen

   

6-Sialyl-N-acetyllactosamine

(2S,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-4,6-dihydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C25H42N2O19 (674.2382)


6-Sialyl-N-acetyllactosamine is an oligosaccharide widely distributed among tissues and is involved in biological processes such as the regulation of the immune response and the progression of colon cancer. Sialylation represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. Sialic acid is commonly found alpha,3- or alpha,6-linked to galactose (Gal), alpha,6-linked to N-acetylgalactosamine (GalNAc) or alpha,8-linked to another sialic acid. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. The b-galactoside a2,6 sialyltransferase (EC 2.4.99.1, ST6Gal.I) is the only sialyltransferase so far identified able to catalyze the a2,6-sialylation of lactosamine. Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. The level of expression of the sialyl-alpha2,6-lactosaminyl structures and of ST6Gal.I show a strong dependence on neoplastic transformation and differentiation in several tissues. (PMID: 11425186) [HMDB] 6-Sialyl-N-acetyllactosamine is an oligosaccharide widely distributed among tissues and is involved in biological processes such as the regulation of the immune response and the progression of colon cancer. Sialylation represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. Sialic acid is commonly found alpha,3- or alpha,6-linked to galactose (Gal), alpha,6-linked to N-acetylgalactosamine (GalNAc) or alpha,8-linked to another sialic acid. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. The b-galactoside a2,6 sialyltransferase (EC 2.4.99.1, ST6Gal.I) is the only sialyltransferase so far identified able to catalyze the a2,6-sialylation of lactosamine. Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. The level of expression of the sialyl-alpha2,6-lactosaminyl structures and of ST6Gal.I show a strong dependence on neoplastic transformation and differentiation in several tissues. (PMID: 11425186).

   

Disialosyl galactosyl globoside

(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-oxohexyl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C36H59N3O27 (965.3336)


Disialylgalactosylgloboside is a renal cell carcinoma (RCC)-associated antigen which mediates adhesion of RCC TOS-1 cells to certain lung tissue target cells. This adhesion process may initiate preferential lung metastasis of RCC (PMID: 10675485). Biosynthesis of disialylgalactosylgloboside (DSGG) is mediated by sialyltransferases from MSGG (monosialylgalactosylgloboside) (PMID: 17123352). Antidisialosyl antibodies have been found in some patients with chronic idiopathic ataxic neuropathy (CIAN) (PMID: 12420092). Globosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Globosides are cerebrosides that contain additional carbohydrates, predominantly galactose, glucose or GalNAc. Lactosyl ceramide is a globoside found in erythrocyte plasma membranes. Globotriaosylceramide (also called ceramide trihexoside) contains glucose and two moles of galactose and accumulates, primarily in the kidneys, of patients suffering from Fabry disease. Disialylgalactosylgloboside is a renal cell carcinoma (RCC)-associated antigen which mediates adhesion of RCC TOS-1 cells to certain lung tissue target cells. This adhesion process may initiate preferential lung metastasis of RCC. (PMID: 10675485). Biosynthesis of disialylgalactosylgloboside (DSGG)is mediated by sialyltransferases from MSGG (monosialylgalactosylgloboside) (PMID: 17123352). Antidisialosyl antibodies have been found in some patients with chronic idiopathic ataxic neuropathy (CIAN) (PMID: 12420092)

   

Sialyllacto-N-tetraose a

(2S,4S,5R)-2-{[(2R,3R,4S,5S,6R)-2-{[(2S,3R,5S,6R)-2-{[(2R,3S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C37H62N2O29 (998.3438)


Sialyllacto-N-tetraose a is a sialyl oligosaccharide found in human breast milk/colostrum which has biological significance with respect to anti-adhesion of pathogenic organism, providing precursors for biosynthesis of the brain and so on. It was found that the concentration level of Sialyllacto-N-teraose a in human colostrum is higher on day 3 than on day 1 collected from the start of lactation. (PMID:17587674) [HMDB] Sialyllacto-N-tetraose a is a sialyl oligosaccharide found in human breast milk/colostrum which has biological significance with respect to anti-adhesion of pathogenic organism, providing precursors for biosynthesis of the brain and so on. It was found that the concentration level of Sialyllacto-N-teraose a in human colostrum is higher on day 3 than on day 1 collected from the start of lactation. (PMID:17587674).

   

Sialyllacto-N-neotetraose c

(2R,4S,5R,6R)-2-{[(3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C37H62N2O29 (998.3438)


Sialyllacto-N-neotetraose c is an oligosaccharide found in human breast milk. Two additional sialylated pentasaccharides include sialyllacto-N-tetraose-a and -b. Oligosaccharides containing N-acetyl (or N-glycolyl) neuraminic acid, i.e. sialylated oligosaccharides, are important components of glycoproteins and glycolipids. In nature, sialylated oligosaccharides often occur as homologous series, with incremental differences in composition, and as structural isomers with subtle differences in monosaccharide sequence and glycosyl linkage and, possibly, with presence or absence of molecular branching. A large number of such sialylated oligosaccharides occur in human milk, where they may have important biological functions. Major structural isomers of these acidic oligosaccharides in human milk are 3- and 6-sialyllactoses and the sialyllacto-N-tetraoses; appreciable amounts of 3- and 6-sialyllactosamines are found in human urine. (PMID:11471815). Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. Neutral milk oligosaccharides vary among individuals and over the course of lactation. (PMID:10683228). Sialyllacto-N-neotetraose c is an oligosaccharide found in human breast milk. Two additional sialylated pentasaccharides include sialyllacto-N-tetraose-a and -b. Oligosaccharides containing N-acetyl (or N-glycolyl) neuraminic acid, i.e. sialylated oligosaccharides, are important components of glycoproteins and glycolipids. In nature, sialylated oligosaccharides often occur as homologous series, with incremental differences in composition, and as structural isomers with subtle differences in monosaccharide sequence and glycosyl linkage and, possibly, with presence or absence of molecular branching. A large number of such sialylated oligosaccharides occur in human milk, where they may have important biological functions. Major structural isomers of these acidic oligosaccharides in human milk are 3- and 6-sialyllactoses and the sialyllacto-N-tetraoses; appreciable amounts of 3- and 6-sialyllactosamines are found in human urine. (PMID:11471815)

   

Disialyllacto-N-tetraose

(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-3-hydroxy-5-[(1-hydroxyethylidene)amino]oxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C48H79N3O37 (1289.4392)


Disialyllacto-N-tetraose is a sialyl hexasaccharide from human milk, which has also been isolated from the urine of pregnant women and has also been found in the feces of preterm human newborns. Its structure is that of lacto-N-tetraose with one of the residues of sialic acid linked alpha-(2->3) to the terminal nonreducing residue of D-galactose and the other sialic acid residue linked alpha-(2->6) to the N-acetyl-D-glucosamine residue. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID:10683228, 809156, 5363606, 1000529, 3421714) [HMDB] Disialyllacto-N-tetraose is a sialyl hexasaccharide from human milk, which has also been isolated from the urine of pregnant women and has also been found in the feces of preterm human newborns. Its structure is that of lacto-N-tetraose with one of the residues of sialic acid linked alpha-(2->3) to the terminal nonreducing residue of D-galactose and the other sialic acid residue linked alpha-(2->6) to the N-acetyl-D-glucosamine residue. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID:10683228, 809156, 5363606, 1000529, 3421714).

   

Sialyllacto-N-tetraose b

(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-3-hydroxy-5-[(1-hydroxyethylidene)amino]-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C37H62N2O29 (998.3438)


Sialyllacto-N-tetraose b is a sialylated oligosaccharide normally occurring in human breast milk. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. The acidic oligosaccharides of human milk are predominantly sialyloligosaccharides. Pathogens that bind sialic acid-containing glycans on their host mucosal surfaces may be inhibited by human milk sialyloligosaccharides. Sialyl oligosaccharides of human milk/colostrum are generally believed to be of biological significance, for example providing precursors for biosynthesis of brain. The levels of sialyllacto-N-tetraose are higher on day 3 than on day 1. These results are consistent with the view that during the first 3 d of lactation, the concentration of sialyl oligosaccharides in human colostrum change in accordance with the physiological demands of newborn infants. (PMID:9426699, 2318868, 10683228, 1778981, 17761135, 17587674) [HMDB] Sialyllacto-N-tetraose b is a sialylated oligosaccharide normally occurring in human breast milk. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. The acidic oligosaccharides of human milk are predominantly sialyloligosaccharides. Pathogens that bind sialic acid-containing glycans on their host mucosal surfaces may be inhibited by human milk sialyloligosaccharides. Sialyl oligosaccharides of human milk/colostrum are generally believed to be of biological significance, for example providing precursors for biosynthesis of brain. The levels of sialyllacto-N-tetraose are higher on day 3 than on day 1. These results are consistent with the view that during the first 3 d of lactation, the concentration of sialyl oligosaccharides in human colostrum change in accordance with the physiological demands of newborn infants. (PMID:9426699, 2318868, 10683228, 1778981, 17761135, 17587674).

   

Sialyl Lewisa penta

(2S,4S,5R,6R)-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C43H72N2O33 (1144.4017)


Sialyl Lewisa pentasaccharide is a human E-selectin (endothelial adhesion molecule) ligand. The cell adhesion molecule E-selectin, which is expressed on cytokine-stimulated endothelial cells, binds to neutrophils, monocytes, and a subpopulation of memory T-cells. This protein has an established role at the initial stepins the recruitment of leukocytes to sites of inflammation, and there is also much interest in the part that it plays in the hematogenous spread of cancer cells. Interference with selectin binding results in inhibition of the later steps that promote leukocyte extravasation. There is therefore much interest in defining the ligands that support adhesion, as a lead to design of adhesion inhibitors that may serve as drugs for the treatment of disorders of inflammation and for minimizing risk of metastasis during surgical resections of tumors.

As predicted from the presence of a lectin-like module at the amino-terminal endof the extracellular domain, E-selectin is a carbohydrate-binding protein. The established ligands for E-selectin include a family of blood group-related fucooligosaccharides that occur as differentiation antigens of granulocytes and monocytes (Lex and 3-sialyl-Lex) and of epithelial tumors (Lea and 3-sialyl-Lea). Adhesion to the sialyl antigens is substantially greater than to the asialo analogues (PMID:7507478)

.

Sialyl Lewisa pentasaccharide is a human E-selectin (endothelial adhesion molecule) ligand. The cell adhesion molecule E-selectin, which is expressed on cytokine-stimulated endothelial cells, binds to neutrophils, monocytes, and a subpopulation of memory T-cells. This protein has an established role at the initial stepins the recruitment of leukocytes to sites of inflammation, and there is also much interest in the part that it plays in the hematogenous spread of cancer cells. Interference with selectin binding results in inhibition of the later steps that promote leukocyte extravasation. There is therefore much interest in defining the ligands that support adhesion, as a lead to design of adhesion inhibitors that may serve as drugs for the treatment of disorders of inflammation and for minimizing risk of metastasis during surgical resections of tumors.

   

3'-Sialyllactosamine

(2S,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-5-amino-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C23H40N2O18 (632.2276)


3-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228)

.

Helicobacter pylori-induced activation of neutrophils occurs by lectinophagocytosis, the recognition of sialylated glycoconjugates (3-sialyllactosamine was the most efficient inhibitor) on the neutrophil cell surface by a bacterial adhesin leads to phagocytosis and an oxidative burst with the production of reactive oxygen metabolites. (PMID: 11087709)

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3-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228)

   

LS tetrasaccharide d

(2S,4S,5R,6R)-2-{[(2S,3R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C37H62N2O29 (998.3438)


LS tetrasaccharide d is a human milk oligosaccharide. (PMID:16603372) [HMDB] LS tetrasaccharide d is a human milk oligosaccharide. (PMID:16603372).

   

Sialyl Lex penta

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-4-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C43H72N2O33 (1144.4017)


In human leukocytes, sialyl Lex determinants bind selectins expressed on the blood vessel, endothelial cells and platelets, causing various cellular interactions and inducing inflammation. The sialyl Lex determinants of CD11/CD18 are shown to bind to E-selection in vitro, suggesting their involvement in the selectin-mediated adhesion process. ("Biology of the Sialic Acids" by Abraham Rosenberg) [HMDB] In human leukocytes, sialyl Lex determinants bind selectins expressed on the blood vessel, endothelial cells and platelets, causing various cellular interactions and inducing inflammation. The sialyl Lex determinants of CD11/CD18 are shown to bind to E-selection in vitro, suggesting their involvement in the selectin-mediated adhesion process. ("Biology of the Sialic Acids" by Abraham Rosenberg).

   

Sialyl Lex tetra

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-6-{[(2R,3R,4S,5R)-2,4,5,6-tetrahydroxy-1-oxohexan-3-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C37H62N2O28 (982.3489)


Sialyl Lewis X (sLeX) is a tetra-saccharide glycoconjugate of membrane proteins. It acts as a ligand for the selectin proteins during cell adhesion of inflammatory process. Aberrant overexpression of sLeX is also a characteristic of various cancer cells, especially for highly malignant ones. In this paper, the sLeX-specific RNA aptamer was selected using a random RNA library and its affinity and specificity were measured by Surface Plasmon Resonance technique. (PMID: 11178986 ) [HMDB] Sialyl Lewis X (sLeX) is a tetra-saccharide glycoconjugate of membrane proteins. It acts as a ligand for the selectin proteins during cell adhesion of inflammatory process. Aberrant overexpression of sLeX is also a characteristic of various cancer cells, especially for highly malignant ones. In this paper, the sLeX-specific RNA aptamer was selected using a random RNA library and its affinity and specificity were measured by Surface Plasmon Resonance technique. (PMID: 11178986).

   

Sialyllacto-N-tetraose c

2-({6-[(6-{[3,5-dihydroxy-2-(hydroxymethyl)-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate

C37H62N2O29 (998.3438)


Sialyllacto-N-tetraose c is a sialylated oligosaccharide normally occurring in human breast milk. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. The acidic oligosaccharides of human milk are predominantly sialyloligosaccharides. Pathogens that bind sialic acid-containing glycans on their host mucosal surfaces may be inhibited by human milk sialyloligosaccharides. Sialyl oligosaccharides of human milk/colostrum are generally believed to be of biological significance, for example providing precursors for biosynthesis of brain. The levels of sialyllacto-N-tetraose are higher on day 3 than on day 1. These results are consistent with the view that during the first 3 d of lactation, the concentration of sialyl oligosaccharides in human colostrum change in accordance with the physiological demands of newborn infants. (PMID: 9426699, 2318868; 10683228, 1778981, 17761135, 17587674) [HMDB] Sialyllacto-N-tetraose c is a sialylated oligosaccharide normally occurring in human breast milk. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. The acidic oligosaccharides of human milk are predominantly sialyloligosaccharides. Pathogens that bind sialic acid-containing glycans on their host mucosal surfaces may be inhibited by human milk sialyloligosaccharides. Sialyl oligosaccharides of human milk/colostrum are generally believed to be of biological significance, for example providing precursors for biosynthesis of brain. The levels of sialyllacto-N-tetraose are higher on day 3 than on day 1. These results are consistent with the view that during the first 3 d of lactation, the concentration of sialyl oligosaccharides in human colostrum change in accordance with the physiological demands of newborn infants. (PMID: 9426699, 2318868; 10683228, 1778981, 17761135, 17587674).

   

Sialyl Lea tetra

(2S,4S,5R)-2-{[(2R,3R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,5S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-{[(2R,3S,4S,5R)-2,4,5,6-tetrahydroxy-1-oxohexan-3-yl]oxy}-5-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C37H62N2O28 (982.3489)


Sialyl Lea tetra is a sialylated oligosaccharide normally occurring in human breast milk, with N-acetylglucosamine as the reducing-end residue. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. Sialyl Lewis a is increasingly expressed in melanoma cells, and hypothetically immunotherapy eliciting a humoral response could be therapeutically effective against tumors. (PMID: 9426699, 2318868; 10683228, 1778981) [HMDB] Sialyl Lea tetra is a sialylated oligosaccharide normally occurring in human breast milk, with N-acetylglucosamine as the reducing-end residue. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. Sialyl Lewis a is increasingly expressed in melanoma cells, and hypothetically immunotherapy eliciting a humoral response could be therapeutically effective against tumors. (PMID: 9426699, 2318868; 10683228, 1778981).

   

O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-Gluc

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C51H85N3O39 (1363.476)


O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-Glucose is a naturally occurring sialylated oligosaccharide. Oligosaccharide chains in glycoproteins, glycolipids, and proteoglycans have been reported which reveal that carbohydrate structures participate in various biological events as well as in modifying protein function. (PMID: 16503611) [HMDB] O-(N-acetyl-α-neuraminosyl)-(2->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)- D-Gluc is a naturally occurring sialylated oligosaccharide. Oligosaccharide chains in glycoproteins, glycolipids, and proteoglycans have been reported which reveal that carbohydrate structures participate in various biological events as well as in modifying protein function. (PMID: 16503611).

   

O-6-deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)]-O-2-

(2R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-({[(3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C57H95N3O43 (1509.5339)


O-6-deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-Glucose is an oligosaccharide isolated from human milk. (PMID: 3182857) [HMDB] O-6-deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-Glucose is an oligosaccharide isolated from human milk. (PMID: 3182857).

   

Disialyllacto-N-fucopentaose II

(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-[(1-hydroxyethylidene)amino]-3-{[(2S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C54H89N3O41 (1435.4971)


Disialyllacto-N-fucopentaose II is a sialylated oligosaccharide of human milk. Neutral milk oligosaccharides vary among individuals and over the course of lactation. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID: 10683228, 1778981, 2327786) [HMDB] Disialyllacto-N-fucopentaose II is a sialylated oligosaccharide of human milk. Neutral milk oligosaccharides vary among individuals and over the course of lactation. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID: 10683228, 1778981, 2327786).

   

Neu5Aca2-3Galb1-3GlcN(Neu5Aca2-6)(Fuca1-4)Acb1-3Galb1-4Glc

2-({2-[(2-{[3,5-dihydroxy-2-(hydroxymethyl)-6-({1,2,5-trihydroxy-6-oxo-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-3-yl}oxy)oxan-4-yl]oxy}-5-hydroxy-6-[({4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxan-2-yl}oxy)methyl]-3-[(1-hydroxyethylidene)amino]oxan-4-yl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate

C53H89N3O39 (1391.5073)


Neu5Aca2-3Galb1-3GlcN(Neu5Aca2-6)(Fuca1-4)Acb1-3Galb1-4Glc is a disialylated oligosaccharide from human breast milk. (PMID:2327786) [HMDB] Neu5Aca2-3Galb1-3GlcN(Neu5Aca2-6)(Fuca1-4)Acb1-3Galb1-4Glc is a disialylated oligosaccharide from human breast milk. (PMID:2327786).

   

Disialyllacto-N-hexaose II

2-[(4-{[4-({2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxan-2-yl}oxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-({3,5-dihydroxy-2-[({4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)methyl]-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl}oxy)-3-hydroxy-5-[(1-hydroxyethylidene)amino]oxan-2-yl)methoxy]-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate

C62H102N4O47 (1654.5714)


Disialyllacto-N-hexaose II is a sialylated oligosaccharide of human milk. Neutral milk oligosaccharides vary among individuals and over the course of lactation. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID: 10683228, 1778981) [HMDB] Disialyllacto-N-hexaose II is a sialylated oligosaccharide of human milk. Neutral milk oligosaccharides vary among individuals and over the course of lactation. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID: 10683228, 1778981).

   

6'-Sialyllactosamine

(2R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-5-amino-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

C23H40N2O18 (632.2276)


6-Sialyllactosamine is one of the most abundant sialyloligosaccharide found in bovine milk. One of the most abundant sialyloligosaccharide found in bovine milk.

   

NeuNGc

(4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C11H19NO10 (325.1009)


NeuNGc, also known as N-Glycolylneuraminic acid or Neu5GC, is classified as a member of the N-acylneuraminic acids. N-acylneuraminic acids are neuraminic acids carrying an N-acyl substituent. NeuNGc is considered to be soluble (in water) and acidic

   

(2R,4R,5S,6S)-2,4-Dihydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

(2S,4S,5R,6R)-2,4-Dihydroxy-5-(2-hydroxyacetamido)-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate

C11H19NO10 (325.1009)


Isolated from beef serum

   

3'-Sialyl-N-acetyllactosamine

2-{[2-({4,6-dihydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl}oxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate

C25H42N2O19 (674.2382)


   

3h-Sialic acid

2,4-Dihydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate

C11H19NO9 (309.106)


   

Neu5NAcalpha2->6lactose

4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(3,4,5-trihydroxy-6-{[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl)methoxy]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C23H39NO19 (633.2116)


   

NeuAc(alpha->6)GalNAc(alpha1->O)Ser

2-{[6-(2-amino-2-carboxyethoxy)-5-acetamido-3,4-dihydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C22H37N3O16 (599.2174)


   

sialyl Lewis x antigen

2-{[3,5-dihydroxy-2-({6-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl}oxy)-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate

C31H52N2O23 (820.2961)


   

sialyl-lewisx

2-{[2-({1,2-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-oxo-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-3-yl}oxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylate

C31H52N2O23 (820.2961)