N-Acetylneuraminic acid (NeuAc) (CAS: 131-48-6), also known as sialic acid, is an acetyl derivative of the amino sugar neuraminic acid. It occurs in many glycoproteins, glycolipids, and polysaccharides in both mammals and bacteria. The most abundant sialic acid, NeuAc, is synthesized in vivo from N-acetylated D-mannosamine (ManNAc) or D-glucosamine (GlcNAc). NeuAc and its activated form, CMP-NeuAc, are biosynthesized in five consecutive reactions that form the intermediates UDP-N-acetylglucosamine (UDP-GlcNAc), N-acetylmannosamine (ManNAc), ManNAc 6-phosphate, NeuAc 9-phosphate, and CMP-NeuAc. CMP-NeuAc is transported into the Golgi apparatus and, with the aid of specific sialyltransferases, added onto nonreducing positions on oligosaccharide chains of glycoproteins and glycolipids. NeuAc is widely distributed throughout human tissues and found in several fluids, including serum, cerebrospinal fluid, saliva, urine, amniotic fluid, and breast milk. It is found in high levels in the brain, adrenal ...

Gangliosides are sialic acid-containing glycosphingolipids expressed on all vertebrate cells. They are primarily positioned in the plasma membrane, with the ceramide part anchored in the membrane and the glycan part exposed on the surface of the cell. These lipids have highly diverse structures, not the least with respect to their carbohydrate chains, with N-acetylneuraminic acid (NeuAc) and N-glycolylneuraminic acid (NeuGc) being the two most common sialic acid residues in mammalian cells. Human healthy tissue is deficient in NeuGc, but since this molecule is expressed in tumors and in human fetal tissues, it is known as an onco-fetal antigen. Gangliosides perform important functions through carbohydrate-specific interactions with proteins, for example as receptors in cell-cell recognition, which can be exploited by viruses and other pathogens, and also by regulating signaling proteins through lateral interaction in the membrane. Through both mechanisms, tumor-associated gangliosides may affect

Rabbit-generated antithymocyte globulins (ATGs), which target human T cells, are widely used as immunosuppressive agents during treatment of kidney allograft recipients. However, ATGs can induce immune complex diseases, including serum sickness disease (SSD). Rabbit and human IgGs have various antigenic differences, including expression of the sialic acid Neu5Gc and α-1-3-Gal (Gal), which are not synthesized by human beings. Moreover, anti-Neu5Gc antibodies have been shown to preexist and be elicited by immunization in human subjects. This study aimed to assess the effect of SSD on long-term kidney allograft outcome and to compare the immunization status of grafted patients presenting with SSD following ATG induction treatment.. ...

We have produced over 30 peer-reviewed publications concerning mesenchymal stromal/stem cell (MSC) research with focus areas on e.g. MSC biodistribution and targeting and MSC markers.. Selected references:. Kerkelä E, Hakkarainen T, Mäkelä T, Raki M, Kampur O, Kilpinen L, Nikkilä J, Lehtonen S, Ritamo I, Pernu R, Pietilä M, Takalo R, Juvonen T, Bergström K, Kalso E, Valmu L, Laitinen S, Lehenkari P, Nystedt J. Transient Proteolytic Modification of Mesenchymal Stromal Cells Increases Lung Clearance Rate and Targeting to Injured Tissue. Stem Cells Transl Med. 2013;2(7):510-20. (inaugural IF 3.596). PM: 23734061. Nystedt J, Anderson H, Hirvonen T, Impola U, Jaatinen T, Heiskanen A, Blomqvist M, Satomaa T, Natunen J, Saarinen J, Lehenkari P, Valmu L, Laine J. Human CMP-N-acetylneuraminic acid hydroxylase is a novel stem cell marker linked to stem cell-specific mechanisms. Stem Cells. 2010;28(2):258-67. (IF 7.781). PM: 19890979. Nystedt J, Anderson H, Tikkanen J, Pietilä M, Hirvonen T, Takalo ...

Hydrolyzes the N-glycolyl group from N-glycolylglucosamine 6-phosphate (GlcNGc-6-P) in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway.

Sialic acid is a general term for N or O substituted derivatives of neuraminic acid (a 9-carbon backbone monosaccharide) which are widely expressed terminal carbohydrates on cell surface glycoproteins and glycolipids of eukaryotic cells.

Based on a strategy previously reported by us, we have synthesized D-xylo configured cyclohexenephosphonates designed to mimic the transition state of the sialidase reaction. The double bond orientation corresponds to the benchmark inhibitor Neu5Ac2en and we could selectively introduce hydroxyalkyl substituents in order to simulate the glycerol side-chain of neuraminic acid. The inhibitory activity of a set of compounds towards bacterial sialidases was tested and interesting differences in activity were found. (C) 2003 Elsevier Ltd. All rights reserved.. ...

A recent study from the Varki lab has confirmed that sialic acid, Neu5Gc, is capable of incorporating into mouse cells through the consumption of red meat, which leads to increased incidence of hepatocellular carcinomas when administered with anti- Neu5Gc antibodies. This blog discusses the implications of red meat consumption in humans and the characterization Neu5Gc as a xeno-autoantigen capable of inducing low level inflammation leading to cancer.

For the first time, the N-glycosylation patterns of immunoglobulin G (IgGs) isolated from the serum of two varieties of knockout pigs (lacking N-glycolylneuraminic acid..

Adenocarcinoma, Animal, Ascitic-Fluid: cy, Binding-Sites-Antibody, Cells-Cultured, Complement, Cytotoxicity-Tests-Immunologic, Female, Male, Mammary-Neoplasms-Experimental, Mice, Neoplasm-Transplantation, Neuraminic-Acids: an, Neuraminidase, Vibrio: en. ...

Recombinant N-Acetylneuraminic Acid Synthase (NANS) Protein. Species: Human. Source: Escherichia coli (E. coli). Order product ABIN6381569.

Two to three million years ago, our pre-human ancestors had a single genetic mutation in their CMAH gene that protected them from a deadly form of malaria but set them up for risk for heart attacks that increases when they eat a lot of meat from any kind of mammal (PNAS, July 22, 2019). No other mammals developed this genetic mutation.. Apes, gorillas, chimpanzees, and other human progenitors were dying from a type of malaria called Plasmodium reichenowi. Then along came a pre-human with a CMAH gene changed from making a cell surface sugar-protein called Neu5Gc to another molecule called Neu5Ac (Proc Natl Acad Sci USA, Sept 6, 2005;102(36): 12819-12824). That pre-human did not die from malaria like other apes, monkeys and gorillas, so his or her children lived and proliferated, and today all humans have Neu5Ac instead of Neu5Gc. Chimpanzees share more than 99 percent of their genes with modern humans, but the CMAH gene is one of the areas of difference. As often happens in nature, the malaria ...

Existing data about Neu5Gc in human cells is controversial (16, 18, 19, 21, 22). Even in studies claiming its presence in malignant tissues, the cell type specificity of the presumed Neu5Gc was not defined. We have advanced understanding of this issue by using an affinity-purified polyclonal antibody against Neu5Gc. Our data support prior reports of Neu5Gc in human cancers and extends the finding to normal and fetal human tissues. Of course, despite our extensive efforts to define specificity, we cannot rule out the possibility of an unexpected epitope cross-reactive with this polyclonal antibody. Thus, we confirmed the presence of Neu5Gc in the normal human tissues with MS.. The inactivating mutation of CMAH in humans is genetically irreversible, no human genes have homology to CMAH, and evidence for an alternate biosynthetic pathway is lacking. Although human cells cultured in FCS appear to incorporate Neu5Gc (8, 24), this could be just passive adsorption. For example, glycolipids containing ...

Ganglioside GM1 (18:1/12:0) is a glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GM1 carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues. Gangliosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Gangliosides are very similar to globosides except that they also contain N-acetyl neuraminic acid (NANA) in varying amounts. The specific names for the gangliosides provide information about their structure. The letter G refers to ganglioside, and the subscripts M, D, T and Q indicate that the molecule contains mono-, ...

Li, Y.T.; Mazzotta, M.Y.; Wan, C.C.; Orth, R.; Li, S.C., 1973: Hydrolysis of Tay-Sachs ganglioside by beta-hexosaminidase A of human liver and urine

This week, Dr. Ajit Varki of the University of California at San Diego showed for the first time that feeding genetically-engineered mice a sugar called Neu5Gc, found in red meat, caused them to produce anti-Neu5Gc antibodies that caused spontaneous cancers (Proceedings of the National Academy of Sciences, published online Dec. 29, 2014).. Several previous studies have shown that eating red meat is associated with increased risk for cancers, diabetes and heart attacks (JAMA Internal Medicine, June 2013). Substituting other protein sources, such as fish, poultry, nuts or legumes, is associated with a reduced risk of death (Archives of Internal Medicine, March 12, 2012). However, epidemiological studies only show an association between eating red meat and cancers; they do not show that eating red meat causes cancer. This new study is the first to show that feeding a component of red meat to mice causes cancers. If future studies confirm this finding, I believe that Ajit Varki will be a strong ...

Neuraminidase, 1 ml. Neuraminidases or sialidases are exoglycosidases that catalyze the cleavage of a glycosidically linked terminal N acetyl neuraminic acid from sialylated glycoconjugates.

We have found that the entrapment of neuraminidase-treated lymphocytes in the liver leads to the induction of autoimmune cellular cytotoxic reactions.. Lymphocytes from mouse spleen and thymus were incubated with neuraminidase in vitro and injected i.v. into syngeneic recipients. Lymphocytic infiltrations into the liver were seen 7 days later with both types of cells. After repeated weekly injections of asialo-lymphocytes, destruction of liver tissue became apparent. Electronmicroscopic studies showed that hepatocytes, fat storage cells, and endothelial cells were affected, mainly at the hepatic periphery.. It is concluded that the adhesion of asialo-lymphocytes to liver cells induces their cytotoxic activity. Similar reactions may occur after paramyxovirus infection due to the action of viral neuraminidase.. ...

Video articles in JoVE about sambucus nigra include Chemically-blocked Antibody Microarray for Multiplexed High-throughput Profiling of Specific Protein Glycosylation in Complex Samples, Using Unfixed, Frozen Tissues to Study Natural Mucin Distribution, A Lectin HPLC Method to Enrich Selectively-glycosylated Peptides from Complex Biological Samples, Profiling Anti-Neu5Gc IgG in Human Sera with a Sialoglycan Microarray Assay .

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Although earlier studies claimed the absence of Neu5Gc from normal human tissues, we showed thatit is also present in smaller amounts in normal human epithelial and endothelial cells in vivo (Tangvoranuntakul et al. 2003). Furthermore, we recently demonstrated that mice with a human-likedefect in the CMAH gene had no detectable Neu5Gc (Hedlund et al. 2007), effectively ruling out an alternate mammalian pathway for synthesis. This paradox is explained by our finding that humans can metabolically incorporate Neu5Gc via oral intake (Tangvoranuntakul et al. 2003). We have therefore suggested that the well-known epidemiological association of human cancers with consumption of red meat and milk (which happen to be the richest dietary sources of Neu5Gc) (Rose et al. 1986; Norat et al. 2002; Lewin et al. 2006) might be related to this unusual metabolic accumulation. Here, we have demonstrated another required component for this hypothesis - circulating antibodies that can recognize Neu5Gc on human ...

Iwata, Y., Suzuki, O. and Wakabayashi, S. (2013), Decreased surface sialic acid content is a sensitive indicator of muscle damage. Muscle Nerve, 47: 372-378. doi: 10.1002/mus.23632 ...

Tumor cells of various origins feature increased expression of sialic acid sugars on membrane glycoproteins and glycolipids and their secretion into the tumor microenvironment. Sialic acids are synthesized in and expressed by essentially every vertebrate cell, and are involved in multiple different physiologic processes. However, hypersialylation of tumor cells relative to their untransformed normal counter parts specifically benefits tumor cell growth and correlates with a poor prognosis for patients with cancer (1, 2). Sialic acids comprise a family of more than 50 carbohydrates that share a nine-carbon backbone (C1-9) to which specific chemical modifications are enzymatically attached inside the cell. The most common sialic acid derivate found in mammals is N-Acetylneuraminic acid (Neu5Ac) which bears an acetyl group on the fifth carbon atom (C5). In general, sialic acids terminate the outer end of glycans (sialoglycans), where they are enzymatically linked to other carbohydrates, such as the ...

Aliases : Solyc01g080900.3. Description : 17.6.1.4 hormone metabolism.gibberelin.synthesis-degradation.ent-kaurenoic acid hydroxylase/oxygenase ent-kaurenoic acid hydroxylase (KAO2) ent-kaurenoic acid hydroxylase 2 (KAO2). ...

In N-acetylneuraminic acid, apart from O9 and O8, a possible glycosylation site is the O4 position. For example, gangliosides HLG-2 and HPG-7 are considered to be potential lead compounds for carbohydrate-based drug development to treat neural disorders. However, the construction of their α(1 → 4) fucosyl sialic acid and α(2 → 4) linkages between sialic acids is difficult because of the regioselec ...

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Export GlyConnect composition list related to glycosylation_site_structure with id 10100000001015 Hex:1 HexNAc:1 NeuAc:1 NeuGc:1 # id : 51 / avg mass :981.8679 ...

Plasmodium falciparum malaria merozoites require erythrocyte sialic acid for optimal invasion of human erythrocytes. Since mouse erythrocytes have the form of sialic acid found on human erythrocytes (N-acetyl neuraminic acid), mouse erythrocytes were tested for invasion in vitro. The Camp and 7G8 strains of P. falciparum invaded mouse erythrocytes at 17-45% of the invasion rate of human erythrocytes. Newly invaded mouse erythrocytes morphologically resembled parasitized human erythrocytes as shown on Giemsa-stained blood films and by electron microscopy. The rim of parasitized mouse erythrocytes contained the P. falciparum 155-kD protein, which is on the rim of ring-infected human erythrocytes. Camp but not 7G8 invaded rat erythrocytes, indicating receptor heterogeneity. These data suggest that it may be possible to adapt the asexual erythrocytic stage of P. falciparum to rodents. The development of a rodent model of P. falciparum malaria could facilitate vaccine development. ...

We isolated a high-purity carp glycophorin from carp erythrocyte membranes and prepared the oligosaccharide fraction from glycophorin by β-elimination [1]. The oligosaccharide fraction was separated into two components (P-1 and P-2) using a Glyco-Pak DEAE column. These O-linked oligosaccharides (P-1 and P-2) were composed of glucose, galactose, fucose, N-acetylgalactosamine and N-glycolylneuraminic acid (NeuGc). The P-1 and P-2 contained one and two NeuGc residues, respectively, and the P-1 exhibited bacteriostatic activity [1]. Using NMR and GC-MS, we determined that the structure of the bacteriostatic P-1 was NeuGcα2→6 (Fucα1→4) (Glcα1→3) Galβ1→4GalNAc-ol. This O-linked oligosaccharide was unique for a vertebrate with respect to the hexosamine and hexose linkages and its non-chain structure.

Abstract:Background: The metabolic syndrome comprises an array of cardiovascular disease (CVD) risk; the clustering of CVD risk factors in the metabolic syndrome suggests a common underlying mechanism. Circulating serum sialic acid, an inflammatory marker has recently been shown to be a strong predictor of cardiovascular mortality, and obesity-related diseases. Objective: is to study the relationship between serum total sialic acid and metabolic variables in type 2 diabetes with and without metabolic syndrome.Subject and Methods: One hundred type 2 diabetic mellitus patients (52 of them had metabolic syndrome and 48 without it) were recruited from the National Diabetic Center, Al-Mustansiriya University during the period from June 2011 to January 2012. One hundred apparently healthy control matched for age and sex were participated in this study. Fasting venous blood samples were collected from all participants, the level of HbA1c was estimated by high performance liquid chromatography. Total ...

4AHO: Structural Insights Into the Recovery of Aldolase Activity in N-Acetylneuraminic Acid Lyase by Replacement of the Catalytically Active Lysine with Gamma-Thialysine by Using a Chemical Mutagenesis Strategy.

4AMA: Structural Insights Into the Recovery of Aldolase Activity in N-Acetylneuraminic Acid Lyase by Replacement of the Catalytically Active Lysine with Gamma-Thialysine by Using a Chemical Mutagenesis Strategy.

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Complete information for NANS gene (Protein Coding), N-Acetylneuraminate Synthase, including: function, proteins, disorders, pathways, orthologs, and expression. GeneCards - The Human Gene Compendium

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[button size=small text=MSDS & Datasheet link=/wp-content/uploads/media/BCDatasheets_C_10.26/CXXXX/C-6008-25.pdf]N-AcetyIneuraminic Acid, Sialic acid; NANA; Neu5Ac, 25mg

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